Unit 5 — End of Topic Tests (reviewer copy: all keys and model answers visible)
End of Topic Test: What a covalent bond is & Naming molecular compounds & Reading Lewis diagrams & Drawing Lewis diagrams (u05-t1 · 5 forms × 21 items · 105 total)
David's notes for James:
OVERSUBSCRIBED GATE (confirm the two subsumptions): 23 scope lessons CMB-001..023 > 20 objective + 1 FRQ rows (D6 fixes 20+1; third oversubscribed gate after U2-G1/U6-G1). CMB-006 (Prefixes for counting atoms) and CMB-012 (Single, double, and triple bonds) carry no row, each with a recorded subsumption rationale in blueprint.scope_lessons_without_rows: the prefix table is the working vocabulary of THREE placed rows (seq 13 naming applies prefixes, seq 14 decodes them into subscripts, seq 19 prefix-names the molecular member), and bond-multiplicity vocabulary is directly exercised by seq 9 (classify drawn bonds), seq 10 (count shared pairs per bond order) and seq 18 (conversion makes double/triple bonds). Documented side effect: their articles drop out of the V-T7 spec-corpus scan (their instances were hand-watched through QC). Your gate's cold list is ignored per the topic-only ruling (ANSWERS #3).
NUMERIC conventions (confirm, all 20 numeric items): integer:true, unit in answer.unit ('atoms'/'electrons'/'bonds'/'valence electrons'), sigFigs = digit count, precisionAssessed:false + gradingNote (counts have no sig-fig contract — the U2-G1 seq-11 convention), display = the graded value, wrongValueDiagnostics [{value, misconception, feedback}] on all 20 (exported from feedback.anticipatedWrong); internal `check` self-verification expressions are authoring machinery and are NOT exported. The R15 scaffold rows carry `scaffold` = the POST-ANSWER worked solution.
TEXT-ENTRY grading contract (confirm, 15 items): seq 13/19 = typed compound NAMES graded case-insensitively (contract stated in every gradingNote; caseSensitive:false lives on the source forms as authoring machinery), with unelided prefix variants accepted as alternates (tetraphosphorus hexaoxide, diiodine pentaoxide — CMB-007's own extraNotes accept unelided forms); seq 14 = typed FORMULAS, element symbols case-significant (Br is not BR), Unicode-subscript display with the plain-digit typing (BrF5) accepted — nothing typed ever requires sub/superscripts (V-T12). unit:null / sigFigs:null on all 15 by recorded convention (a typed name/formula has neither) — this is the known shared-exporter text-contract scoping gap, SIXTH occurrence (U2-G1/U2-G5/U2-G4/U4-G2/U4-G3/U6-G1 precedents); the gate-local _verify_james_export.py re-runs the full verification suite with the one interaction-scoping correction. wrongValueDiagnostics ride on all 15.
PACKAGING INSTANCE SWEEP (confirm the three re-freshenings — a NEW deterministic check this gate contributes): the shared freshness validator scans the WORD register only, so instances carried as Unicode-subscript FORMULAS or prefix-NAME answer strings are invisible to it. A gate-local packaging sweep (_packaging_instance_sweep.py) checked every bank instance in that register against STUDENT-SEEN scope text and caught three QC-loop replacement instances that were taught in scope: B#8 OF2 -> CH2F2 (OF2's Lewis diagram is practiced in CMB-015/017 fluency and drawn in CMB-020's production), C#13 Cl2O -> SeF4 'selenium tetrafluoride' ('Dichlorine monoxide is Cl2O' is a CMB-008 worked example), D#13 N2O5 -> I2O5 'diiodine pentoxide' (N2O5 is counted in a CMB-005 fluency stem AND the swap had verbatim-recreated your CMB-007 gate item pool[18], already consumed by A#13's placement). All three re-blinded (fresh reviewers, 2/2 key picks + 4/4 typed matches) and re-passed by the authoritative QC model. PROPOSED shared strengthening (documented, not applied — _shared read-only this wave): a formula/name-register V-T7 lane.
RECORDED, NOT PATCHED (sweep judgments — your call if you want swaps): E#10 keeps its PBr3 Lewis-diagram figure although CMB-009 teaches PBr3's NAME in a fluency check — a different skill register (the drawn electron layout E#10 asks about is never shown in scope, so nothing recallable answers it). B#19 runs SO2 'sulfur dioxide' — SO2 appears ONLY in authoring-facing extraNotes (the CMB-013/021 resonance-exclusion lists, never student-seen) and the item is naming-only with no structure implied (B#19's original BCl3 seed instance was swapped because boron is a metalloid outside the taught two-nonmetals prefix branch). Prefix-name FRAGMENT shares (dichloride/dioxide/tetrafluoride/monofluoride...) are inherent naming-system vocabulary — B#13's 'disulfur dichloride' vs the taught 'sulfur dichloride' (SCl2) is the tested di--on-first discrimination, not a leak. E#20 CBr4 and B#8's new CH2F2 appear only in OUT-of-scope later lessons (CMB-024/028/040) — the gate is taken first.
ADJUDICATED INSTANCE FAMILIES (confirm — the gate's structural adjudication): U5-G1's instances are nature-fixed per element (molecules built from the classroom-safe nonmetal palette H/C/N/O/P/S + the four halogens; hydrogen's two-electron count and helium's matching role are literal RULE CONTENT; group numbers 14-17 quoted in-stem ARE the tested group->valence mapping), so cross-slot word/number exclusivity is structurally unsatisfiable. 16 families recorded in gate_config.json (8 element-palette, 3 own-lesson rule/consumed-palette, 5 number families incl. the seq-20 electron totals under CMB-022's stems-supply-the-total specNotes convention), enforced by the gate-local validate_with_adjudications.py wrapper over the UNTOUCHED shared validator (U3-G3 protocol; 519 nature-fixed V-T7 lines 100% excused, 0 uncovered, all other scans fully armed). The proposed shared A7 relief key (U2-G2/_proposed_shared_A7.md) would retire these wrappers — awaiting sign-off. Also recorded: NO extra_task_idioms were needed (the A2 runtime derivation covers every canonical clause) and the detection lexicon was consciously NOT extended (selenium/tellurium/germanium/silicon/... are heavily present in your own spec text; additions would re-flag ledger-audited exactly-once uses — the U4-G1 ADJ-4 lane, you and David decide).
NOTA REPLACEMENTS (ANSWERS #2, confirm): your pool[54] and pool[56] CMB-019 gate items carried a None-of-the-above option -> replaced at A#15 and C#15 with misconception-keyed distractors (A#15: 'the element written first in the formula' — which blind round 1 then caught RESOLVING to the true central atom in SiHCl3, an F2 hard fail, re-keyed to a 'no single central atom' claim; C#15 analogous). No other NOTA/AOTA; V-T5 PASS and the export's own scan re-confirms. The U5 wave note about CMB-028's keyed None-of-the-above (fixed in your v2 specs) was verified N/A at placement — CMB-028 is U5-G2 scope.
SEED CENSUS + FRESHENINGS (SEED RULING — confirm): 48 placements from your pool of 69 (form A 21 / B 16 / C 9 / D 2 — your curation depth; form E fully authored); 23 spares; final census 48 seed-carried / 57 authored. 4 must_freshen + many freshness_same_lesson placements freshened in content with structures/keys/misconception classes kept (P4 particles, SeO3, SeBr4, BrF5, IF7, Mg3N2, HOBr, CHCl3-FRQ, ...); anonymized-atoms license (U3-G3 precedent) exercised at rows 6, 7(B-E), 11(B/C/D), 16(C/D/E), 18 — behavior/rule discriminations that are element-free by design. QC-loop instance swaps on seed slots: B#8 (GeF4 -> OF2 -> CH2F2, see the sweep note), B#19 (BCl3 -> SO2, metalloid branch), plus authored-slot swaps C#13/D#13/E#20 (SnCl4 -> CBr4: tin is a METAL — CMB-009's metal-first->ionic rule contradicts a molecular Lewis premise; same 32-electron total preserved).
FRQ (confirm the topology_change flag): seq 21 = CMB-023's five-step Lewis routine as a typed diagram-PLAN, parts (a) count valence electrons / (b) justify the skeleton / (c) finish the diagram + run both checks; rubric 30/30/40 = 100 split losslessly; molecules CHCl3 / SiBr4 / PF3 / ethanol-with-given-backbone / CH3F. FLAG: your two FRQ-adjacent seeds were CONVERSION cases (OCS, HFCO — both corpus-consumed by CMB-023's own article) and their replacements are NO-conversion cases, making all five forms uniform no-conversion (V-T1 parity); the step-5 conversion skill is assessed at seq 18 (mcq) and seq 20 (checking) instead. Confirm this parity trade. Standing typed-plan delivery note below.
FRQ FIGURE FIELD (delivery note, differs from U6-G1's marker): each exported seq-21 item carries figure = {figureShape: 'model_answer_diagram', modelAnswerFigureSpecs: {c: <the correct finished diagram, structured>}} — this is KEY-SIDE grader material (part (c)'s model drawing), NOT a student-rendered stimulus; never show it before grading. Our blind harness STRIPS it from reviewer packets for exactly that reason (a shared-packet-builder gap, documented for the maintainer). If you prefer the U6-G1 marker-only shape ({figureRequired, figureShape}), say so and we re-cut the export.
IMAGE-OPTION DELIVERY REQUIREMENT (seq 16/17): the key and distractors are the internal ids 'Picture 1..4' (R2 image-XOR-text — the strings are never rendered, never aria) and the actual drawings live in figure.optionFigureSpecs, carried verbatim; the items are answerable ONLY with those option figures rendered (deterministic lewis-diagram/particulate specs, structure strings written to render neutrally per R23). Confirm your renderer ships them; our blind harness needed a gate-local augmenter for these families plus the lewis-diagram stimuli (the shared packet builder's fig_text lacks them and its style strings would leak 'deliberately wrong' — documented, not applied).
OBSCURE-BUT-REAL instances (recorded, R23-covered — figures/context carry everything needed): CSe2, H2S2, CH3SH, H2Te, the IBr/BrF interhalogen panel, and the packaging additions SeF4 + I2O5 (both textbook prefix-naming compounds); BBr3/PBr5 appear at seq 4 as FORMULA-READING only (no Lewis claim). Cross-form near-parallel names recorded (C#13 'selenium tetrafluoride' vs D#19 'selenium hexafluoride'; C#13/E#13 share the 'tetrafluoride' fragment) — different forms, no student sees both.
Instance hygiene (binding course-wide rule, re-swept at packaging): zero uranium/plutonium/radium/actinide/enrichment/reactor/weapon/radiation/fission tokens anywhere in the export (0 hits); the palette is classroom-safe throughout (Rb/Cs/Sr/K/Li/Mg ionic partners, Se/Te/Ge/Sn/Si/B/P/S/N/C/H + halogens, noble gases Ar/Kr/Xe as non-bonding scenery).
FRQ delivery: your `prod` draw-on-paper class is delivered as a typed diagram-PLAN task (state kinds/recipes/counts/spacing; rubric grades the same observables). Confirm this mapping (pending from the U01-G1 round-trip).
full notes file
# u05-t1 — notes/queries from David's side (U5-G1)
1. OVERSUBSCRIBED GATE (confirm the two subsumptions): 23 scope lessons CMB-001..023 > 20 objective + 1 FRQ rows (D6 fixes 20+1; third oversubscribed gate after U2-G1/U6-G1). CMB-006 (Prefixes for counting atoms) and CMB-012 (Single, double, and triple bonds) carry no row, each with a recorded subsumption rationale in blueprint.scope_lessons_without_rows: the prefix table is the working vocabulary of THREE placed rows (seq 13 naming applies prefixes, seq 14 decodes them into subscripts, seq 19 prefix-names the molecular member), and bond-multiplicity vocabulary is directly exercised by seq 9 (classify drawn bonds), seq 10 (count shared pairs per bond order) and seq 18 (conversion makes double/triple bonds). Documented side effect: their articles drop out of the V-T7 spec-corpus scan (their instances were hand-watched through QC). Your gate's cold list is ignored per the topic-only ruling (ANSWERS #3).
2. INTERACTION FORMATS (confirm): per form 13 mcq / 4 numeric ENTRY (seq 4 CMB-005 atom counting, seq 10 CMB-015 electrons-around-an-atom, seq 11 CMB-016 bonds-still-needed, seq 12 CMB-017 valence totals — HS numeric-entry rule, never numeric-answer mcq) / 3 text ENTRY (seq 13 CMB-007 prefix NAME, seq 14 CMB-008 typed FORMULA, seq 19 CMB-009 name-the-molecular-member) / 1 FRQ (seq 21 CMB-023 five-step Lewis routine). Figure rows: seq 5 particulate panels, seq 8/9/10/20 Lewis-diagram stimuli, seq 16/17 image-option items.
3. NUMERIC conventions (confirm, all 20 numeric items): integer:true, unit in answer.unit ('atoms'/'electrons'/'bonds'/'valence electrons'), sigFigs = digit count, precisionAssessed:false + gradingNote (counts have no sig-fig contract — the U2-G1 seq-11 convention), display = the graded value, wrongValueDiagnostics [{value, misconception, feedback}] on all 20 (exported from feedback.anticipatedWrong); internal `check` self-verification expressions are authoring machinery and are NOT exported. The R15 scaffold rows carry `scaffold` = the POST-ANSWER worked solution.
4. TEXT-ENTRY grading contract (confirm, 15 items): seq 13/19 = typed compound NAMES graded case-insensitively (contract stated in every gradingNote; caseSensitive:false lives on the source forms as authoring machinery), with unelided prefix variants accepted as alternates (tetraphosphorus hexaoxide, diiodine pentaoxide — CMB-007's own extraNotes accept unelided forms); seq 14 = typed FORMULAS, element symbols case-significant (Br is not BR), Unicode-subscript display with the plain-digit typing (BrF5) accepted — nothing typed ever requires sub/superscripts (V-T12). unit:null / sigFigs:null on all 15 by recorded convention (a typed name/formula has neither) — this is the known shared-exporter text-contract scoping gap, SIXTH occurrence (U2-G1/U2-G5/U2-G4/U4-G2/U4-G3/U6-G1 precedents); the gate-local _verify_james_export.py re-runs the full verification suite with the one interaction-scoping correction. wrongValueDiagnostics ride on all 15.
5. PACKAGING INSTANCE SWEEP (confirm the three re-freshenings — a NEW deterministic check this gate contributes): the shared freshness validator scans the WORD register only, so instances carried as Unicode-subscript FORMULAS or prefix-NAME answer strings are invisible to it. A gate-local packaging sweep (_packaging_instance_sweep.py) checked every bank instance in that register against STUDENT-SEEN scope text and caught three QC-loop replacement instances that were taught in scope: B#8 OF2 -> CH2F2 (OF2's Lewis diagram is practiced in CMB-015/017 fluency and drawn in CMB-020's production), C#13 Cl2O -> SeF4 'selenium tetrafluoride' ('Dichlorine monoxide is Cl2O' is a CMB-008 worked example), D#13 N2O5 -> I2O5 'diiodine pentoxide' (N2O5 is counted in a CMB-005 fluency stem AND the swap had verbatim-recreated your CMB-007 gate item pool[18], already consumed by A#13's placement). All three re-blinded (fresh reviewers, 2/2 key picks + 4/4 typed matches) and re-passed by the authoritative QC model. PROPOSED shared strengthening (documented, not applied — _shared read-only this wave): a formula/name-register V-T7 lane.
6. RECORDED, NOT PATCHED (sweep judgments — your call if you want swaps): E#10 keeps its PBr3 Lewis-diagram figure although CMB-009 teaches PBr3's NAME in a fluency check — a different skill register (the drawn electron layout E#10 asks about is never shown in scope, so nothing recallable answers it). B#19 runs SO2 'sulfur dioxide' — SO2 appears ONLY in authoring-facing extraNotes (the CMB-013/021 resonance-exclusion lists, never student-seen) and the item is naming-only with no structure implied (B#19's original BCl3 seed instance was swapped because boron is a metalloid outside the taught two-nonmetals prefix branch). Prefix-name FRAGMENT shares (dichloride/dioxide/tetrafluoride/monofluoride...) are inherent naming-system vocabulary — B#13's 'disulfur dichloride' vs the taught 'sulfur dichloride' (SCl2) is the tested di--on-first discrimination, not a leak. E#20 CBr4 and B#8's new CH2F2 appear only in OUT-of-scope later lessons (CMB-024/028/040) — the gate is taken first.
7. ADJUDICATED INSTANCE FAMILIES (confirm — the gate's structural adjudication): U5-G1's instances are nature-fixed per element (molecules built from the classroom-safe nonmetal palette H/C/N/O/P/S + the four halogens; hydrogen's two-electron count and helium's matching role are literal RULE CONTENT; group numbers 14-17 quoted in-stem ARE the tested group->valence mapping), so cross-slot word/number exclusivity is structurally unsatisfiable. 16 families recorded in gate_config.json (8 element-palette, 3 own-lesson rule/consumed-palette, 5 number families incl. the seq-20 electron totals under CMB-022's stems-supply-the-total specNotes convention), enforced by the gate-local validate_with_adjudications.py wrapper over the UNTOUCHED shared validator (U3-G3 protocol; 519 nature-fixed V-T7 lines 100% excused, 0 uncovered, all other scans fully armed). The proposed shared A7 relief key (U2-G2/_proposed_shared_A7.md) would retire these wrappers — awaiting sign-off. Also recorded: NO extra_task_idioms were needed (the A2 runtime derivation covers every canonical clause) and the detection lexicon was consciously NOT extended (selenium/tellurium/germanium/silicon/... are heavily present in your own spec text; additions would re-flag ledger-audited exactly-once uses — the U4-G1 ADJ-4 lane, you and David decide).
8. NOTA REPLACEMENTS (ANSWERS #2, confirm): your pool[54] and pool[56] CMB-019 gate items carried a None-of-the-above option -> replaced at A#15 and C#15 with misconception-keyed distractors (A#15: 'the element written first in the formula' — which blind round 1 then caught RESOLVING to the true central atom in SiHCl3, an F2 hard fail, re-keyed to a 'no single central atom' claim; C#15 analogous). No other NOTA/AOTA; V-T5 PASS and the export's own scan re-confirms. The U5 wave note about CMB-028's keyed None-of-the-above (fixed in your v2 specs) was verified N/A at placement — CMB-028 is U5-G2 scope.
9. SEED CENSUS + FRESHENINGS (SEED RULING — confirm): 48 placements from your pool of 69 (form A 21 / B 16 / C 9 / D 2 — your curation depth; form E fully authored); 23 spares; final census 48 seed-carried / 57 authored. 4 must_freshen + many freshness_same_lesson placements freshened in content with structures/keys/misconception classes kept (P4 particles, SeO3, SeBr4, BrF5, IF7, Mg3N2, HOBr, CHCl3-FRQ, ...); anonymized-atoms license (U3-G3 precedent) exercised at rows 6, 7(B-E), 11(B/C/D), 16(C/D/E), 18 — behavior/rule discriminations that are element-free by design. QC-loop instance swaps on seed slots: B#8 (GeF4 -> OF2 -> CH2F2, see the sweep note), B#19 (BCl3 -> SO2, metalloid branch), plus authored-slot swaps C#13/D#13/E#20 (SnCl4 -> CBr4: tin is a METAL — CMB-009's metal-first->ionic rule contradicts a molecular Lewis premise; same 32-electron total preserved).
10. FRQ (confirm the topology_change flag): seq 21 = CMB-023's five-step Lewis routine as a typed diagram-PLAN, parts (a) count valence electrons / (b) justify the skeleton / (c) finish the diagram + run both checks; rubric 30/30/40 = 100 split losslessly; molecules CHCl3 / SiBr4 / PF3 / ethanol-with-given-backbone / CH3F. FLAG: your two FRQ-adjacent seeds were CONVERSION cases (OCS, HFCO — both corpus-consumed by CMB-023's own article) and their replacements are NO-conversion cases, making all five forms uniform no-conversion (V-T1 parity); the step-5 conversion skill is assessed at seq 18 (mcq) and seq 20 (checking) instead. Confirm this parity trade. Standing typed-plan delivery note below.
11. FRQ FIGURE FIELD (delivery note, differs from U6-G1's marker): each exported seq-21 item carries figure = {figureShape: 'model_answer_diagram', modelAnswerFigureSpecs: {c: <the correct finished diagram, structured>}} — this is KEY-SIDE grader material (part (c)'s model drawing), NOT a student-rendered stimulus; never show it before grading. Our blind harness STRIPS it from reviewer packets for exactly that reason (a shared-packet-builder gap, documented for the maintainer). If you prefer the U6-G1 marker-only shape ({figureRequired, figureShape}), say so and we re-cut the export.
12. IMAGE-OPTION DELIVERY REQUIREMENT (seq 16/17): the key and distractors are the internal ids 'Picture 1..4' (R2 image-XOR-text — the strings are never rendered, never aria) and the actual drawings live in figure.optionFigureSpecs, carried verbatim; the items are answerable ONLY with those option figures rendered (deterministic lewis-diagram/particulate specs, structure strings written to render neutrally per R23). Confirm your renderer ships them; our blind harness needed a gate-local augmenter for these families plus the lewis-diagram stimuli (the shared packet builder's fig_text lacks them and its style strings would leak 'deliberately wrong' — documented, not applied).
13. OBSCURE-BUT-REAL instances (recorded, R23-covered — figures/context carry everything needed): CSe2, H2S2, CH3SH, H2Te, the IBr/BrF interhalogen panel, and the packaging additions SeF4 + I2O5 (both textbook prefix-naming compounds); BBr3/PBr5 appear at seq 4 as FORMULA-READING only (no Lewis claim). Cross-form near-parallel names recorded (C#13 'selenium tetrafluoride' vs D#19 'selenium hexafluoride'; C#13/E#13 share the 'tetrafluoride' fragment) — different forms, no student sees both.
14. Instance hygiene (binding course-wide rule, re-swept at packaging): zero uranium/plutonium/radium/actinide/enrichment/reactor/weapon/radiation/fission tokens anywhere in the export (0 hits); the palette is classroom-safe throughout (Rb/Cs/Sr/K/Li/Mg ionic partners, Se/Te/Ge/Sn/Si/B/P/S/N/C/H + halogens, noble gases Ar/Kr/Xe as non-bonding scenery).
Which sentence states the octet pattern for molecules?
In most stable molecules each atom is surrounded by eight electrons, counting every shared pair for both atoms, while hydrogen is surrounded by two. KEY
In most stable molecules each atom is surrounded by eight electrons, counting every shared pair for only one of its two atoms, while hydrogen is surrounded by two.
In every stable molecule each atom, hydrogen included, is surrounded by eight electrons, counting shared pairs for both atoms.
In most stable molecules each atom is surrounded by eight of its own unshared electrons, with shared pairs left uncounted.
How many bromine atoms are in one molecule of SeBr₄?
Answer: 4 atoms KEY
also accepted: 4 atoms, 4.0
wrongValueDiagnostics
[
{
"value": 1,
"misconception": "you read the first element's count — the subscript 4 sits after Br, so it counts bromine",
"feedback": "This answer is wrong — you read the first element's count — the subscript 4 sits after Br, so it counts bromine."
},
{
"value": 5,
"misconception": "you counted every atom in the molecule — the question asks for the bromine atoms alone",
"feedback": "This answer is wrong — you counted every atom in the molecule — the question asks for the bromine atoms alone."
}
]
feedback
{
"keyExplanation": "The subscript after Br is 4, so one SeBr₄ molecule contains 4 bromine atoms. The selenium, with no subscript, counts as one atom — but it is not bromine.",
"anticipatedWrong": [
{
"value": 1,
"misconception": "you read the first element's count — the subscript 4 sits after Br, so it counts bromine",
"feedback": "This answer is wrong — you read the first element's count — the subscript 4 sits after Br, so it counts bromine."
},
{
"value": 5,
"misconception": "you counted every atom in the molecule — the question asks for the bromine atoms alone",
"feedback": "This answer is wrong — you counted every atom in the molecule — the question asks for the bromine atoms alone."
}
]
}
Diagrams 1 and 2 in the figure each show two bonded atoms, one bond per diagram. Which classification is correct?
FIGURE (particulate-bond-panels · stimulus) — panels: [{"panel": "1", "description": "a circle labeled Rb⁺ and a separate circle labeled F⁻, with a curved arrow showing one electron moved from Rb to F"}, {"panel… · style: "clean textbook particulate diagrams, boxed panels"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "particulate-bond-panels",
"panels": [
{
"panel": "1",
"description": "a circle labeled Rb⁺ and a separate circle labeled F⁻, with a curved arrow showing one electron moved from Rb to F"
},
{
"panel": "2",
"description": "a larger circle labeled Se overlapping a smaller circle labeled H, with two dots in the overlap region"
}
],
"style": "clean textbook particulate diagrams, boxed panels"
}
}
Diagram 1 shows transfer, and diagram 2 shows sharing. KEY
Diagram 1 shows sharing, and diagram 2 shows transfer.
Bond 1: two atoms, X and Y, hold one shared pair of electrons between them. Bond 2: one electron moves completely from atom M onto atom Z. Which classification is correct?
Bond 1 is covalent, and bond 2 is not covalent. KEY
In the Lewis diagram of hydrazine, N₂H₄, shown in the figure, the labels 1 and 2 tag two electron pairs. Which classification is correct?
FIGURE (lewis-diagram · stimulus) — molecule: "N₂H₄" · structure: "two N symbols joined by one line, each N also joined by single lines to two H symbols; one dot pair on each N drawn radially; the N–N line labeled 1, the do… · style: "clean Lewis diagram; lone pairs radial, dots equidistant; pair markers as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "N₂H₄",
"structure": "two N symbols joined by one line, each N also joined by single lines to two H symbols; one dot pair on each N drawn radially; the N–N line labeled 1, the dot pair on the right N labeled 2",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant; pair markers as small numbered arrows"
}
}
Pair 1 is a bonding pair, and pair 2 is a lone pair. KEY
Pair 1 is a lone pair, and pair 2 is a bonding pair.
The figure shows the Lewis diagram of diacetylene, C₄H₂, with the bond between the two middle atoms labeled 1. Classify bond 1.
FIGURE (lewis-diagram · stimulus) — molecule: "C₄H₂" · structure: "H-C≡C-C≡C-H in a row: one line between each H and its C, three lines between the first and second chain atoms and between the third and fourth, one line bet… · style: "clean Lewis diagram; bond labels as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₄H₂",
"structure": "H-C≡C-C≡C-H in a row: one line between each H and its C, three lines between the first and second chain atoms and between the third and fourth, one line between the two middle atoms labeled 1; no dots anywhere",
"style": "clean Lewis diagram; bond labels as small numbered arrows"
}
}
A single bond. KEY
A triple bond.
A double bond.
No bond.
CMB-015 · medium · application · seq 10 · seed:U5-G1/pool[42] (CMB-015 gateItems) — CO2 (015 article instance) -> SeO2 per ledger; double-bond counting facet kept · numeric
The figure shows the Lewis diagram of selenium dioxide, SeO₂, as drawn in this course. How many electrons surround the selenium atom?
FIGURE (lewis-diagram · stimulus) — molecule: "SeO₂" · structure: "Se central; two lines to the left O (a double bond) and one line to the right O (a single bond); one dot pair on the Se; two dot pairs on the double-bonded … · style: "clean textbook Lewis diagram, drawn exactly as described"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SeO₂",
"structure": "Se central; two lines to the left O (a double bond) and one line to the right O (a single bond); one dot pair on the Se; two dot pairs on the double-bonded O; three dot pairs on the single-bonded O; all lone pairs radial",
"style": "clean textbook Lewis diagram, drawn exactly as described"
}
}
Answer: 8 electrons KEY
also accepted: 8 electrons, 8.0
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the pairs, not the electrons — four pairs touch the selenium, and each pair holds two electrons",
"feedback": "This answer is wrong — you counted the pairs, not the electrons — four pairs touch the selenium, and each pair holds two electrons."
},
{
"value": 6,
"misconception": "you counted the double bond as one shared pair — a double bond is two shared pairs, four electrons",
"feedback": "This answer is wrong — you counted the double bond as one shared pair — a double bond is two shared pairs, four electrons."
},
{
"value": 18,
"misconception": "you counted every electron in the diagram — the oxygens' lone pairs belong to the oxygens, not the selenium",
"feedback": "This answer is wrong — you counted every electron in the diagram — the oxygens' lone pairs belong to the oxygens, not the selenium."
}
]
feedback
{
"keyExplanation": "Count what is drawn around the selenium: the double bond is two shared pairs (4 electrons), the single bond is one shared pair (2), and the selenium's own lone pair adds 2. 4 + 2 + 2 = 8 electrons.",
"anticipatedWrong": [
{
"value": 4,
"misconception": "you counted the pairs, not the electrons — four pairs touch the selenium, and each pair holds two electrons",
"feedback": "This answer is wrong — you counted the pairs, not the electrons — four pairs touch the selenium, and each pair holds two electrons."
},
{
"value": 6,
"misconception": "you counted the double bond as one shared pair — a double bond is two shared pairs, four electrons",
"feedback": "This answer is wrong — you counted the double bond as one shared pair — a double bond is two shared pairs, four electrons."
},
{
"value": 18,
"misconception": "you counted every electron in the diagram — the oxygens' lone pairs belong to the oxygens, not the selenium",
"feedback": "This answer is wrong — you counted every electron in the diagram — the oxygens' lone pairs belong to the oxygens, not the selenium."
}
]
}
CMB-016 · medium · application · seq 11 · seed:U5-G1/pool[45] (CMB-016 gateItems) — iodine/Group-17 -> tellurium/Group-16 per ledger (fresh element + fresh value); misconception family kept · numeric
Tellurium is in Group 16, so a tellurium atom has six valence electrons. How many covalent bonds does tellurium typically form?
Answer: 2 bonds KEY
also accepted: 2 bonds, 2.0
scaffold
[
"Write down the values in the question:",
"valence electrons = 6",
"Write down the relationship:",
"typical bonds = 8 − valence electrons",
"Substitute in the values, and calculate:",
"typical bonds = 8 − 6",
"typical bonds = 2"
]
wrongValueDiagnostics
[
{
"value": 16,
"misconception": "you used the group number as the bond count — Group 16 atoms have six valence electrons and need just two more",
"feedback": "This answer is wrong — you used the group number as the bond count — Group 16 atoms have six valence electrons and need just two more."
},
{
"value": 6,
"misconception": "you found the valence count and stopped — six is the valence count, and the bonds equal 8 − 6",
"feedback": "This answer is wrong — you found the valence count and stopped — six is the valence count, and the bonds equal 8 − 6."
},
{
"value": 8,
"misconception": "you answered with the octet target — eight is the electron goal, not the number of bonds",
"feedback": "This answer is wrong — you answered with the octet target — eight is the electron goal, not the number of bonds."
}
]
feedback
{
"keyExplanation": "Write down the values in the question:\nvalence electrons = 6\nWrite down the relationship:\ntypical bonds = 8 − valence electrons\nSubstitute in the values, and calculate:\ntypical bonds = 8 − 6\ntypical bonds = 2",
"anticipatedWrong": [
{
"value": 16,
"misconception": "you used the group number as the bond count — Group 16 atoms have six valence electrons and need just two more",
"feedback": "This answer is wrong — you used the group number as the bond count — Group 16 atoms have six valence electrons and need just two more."
},
{
"value": 6,
"misconception": "you found the valence count and stopped — six is the valence count, and the bonds equal 8 − 6",
"feedback": "This answer is wrong — you found the valence count and stopped — six is the valence count, and the bonds equal 8 − 6."
},
{
"value": 8,
"misconception": "you answered with the octet target — eight is the electron goal, not the number of bonds",
"feedback": "This answer is wrong — you answered with the octet target — eight is the electron goal, not the number of bonds."
}
]
}
CMB-017 · medium · application · seq 12 · seed:U5-G1/pool[48] (CMB-017 gateItems) — PCl3/26 -> SnBr4/32 per stage-2 patched ledger (the CBr4 draft kept 'carbon', an own-lesson 017 material); trap set kept · numeric
Tin is a Group 14 element; bromine is a Group 17 element. For one SnBr₄ molecule, what is the total number of valence electrons?
Answer: 32 valence electrons KEY
also accepted: 32 valence electrons, 32 electrons, 32.0
scaffold
[
"Write down the values in the question:",
"tin: 1 atom × 4 valence electrons",
"bromine: 4 atoms × 7 valence electrons",
"Write down the relationship:",
"total valence electrons = the sum over every element of (atoms × valence electrons)",
"Substitute in the values, and calculate:",
"total valence electrons = (1 × 4) + (4 × 7) = 4 + 28 = 32"
]
wrongValueDiagnostics
[
{
"value": 11,
"misconception": "you counted one bromine — the subscript 4 means four bromine atoms",
"feedback": "This answer is wrong — you counted one bromine — the subscript 4 means four bromine atoms."
},
{
"value": 82,
"misconception": "you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven",
"feedback": "This answer is wrong — you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven."
},
{
"value": 5,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
feedback
{
"keyExplanation": "tin: 1 atom × 4 valence electrons\nbromine: 4 atoms × 7 valence electrons\ntotal valence electrons = (1 × 4) + (4 × 7) = 4 + 28 = 32",
"anticipatedWrong": [
{
"value": 11,
"misconception": "you counted one bromine — the subscript 4 means four bromine atoms",
"feedback": "This answer is wrong — you counted one bromine — the subscript 4 means four bromine atoms."
},
{
"value": 82,
"misconception": "you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven",
"feedback": "This answer is wrong — you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven."
},
{
"value": 5,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
}
CMB-007 · medium · application · seq 13 · seed:U5-G1/pool[18] (CMB-007 gateItems) — N2O5 (007 article instance) -> P4O6 per ledger; elision teaching and wrong-answer diagnostics kept · text
Name the binary molecular compound P₄O₆.
Answer: tetraphosphorus hexoxide KEY
also accepted: tetraphosphorus hexaoxide, Tetraphosphorus hexoxide
wrongValueDiagnostics
[
{
"value": "phosphorus hexoxide",
"misconception": "you dropped tetra- — only mono- is dropped, and only on the first element",
"feedback": "This answer is wrong — you dropped tetra- — only mono- is dropped, and only on the first element."
},
{
"value": "tetraphosphorus oxide",
"misconception": "you left the six oxygens uncounted — the second element needs hex(a)-",
"feedback": "This answer is wrong — you left the six oxygens uncounted — the second element needs hex(a)-."
}
]
feedback
{
"keyExplanation": "Four phosphorus atoms keep tetra-, six oxygens take hexa-, and hexa- + oxide elides to hexoxide. P₄O₆ is tetraphosphorus hexoxide.",
"anticipatedWrong": [
{
"value": "phosphorus hexoxide",
"misconception": "you dropped tetra- — only mono- is dropped, and only on the first element",
"feedback": "This answer is wrong — you dropped tetra- — only mono- is dropped, and only on the first element."
},
{
"value": "tetraphosphorus oxide",
"misconception": "you left the six oxygens uncounted — the second element needs hex(a)-",
"feedback": "This answer is wrong — you left the six oxygens uncounted — the second element needs hex(a)-."
}
]
}
CMB-008 · medium · application · seq 14 · seed:U5-G1/pool[21] (CMB-008 gateItems) — IF5 (008 article instance) -> BrF5 per ledger; diagnostics kept · text
Write the formula of bromine pentafluoride.
Answer: BrF₅ KEY
also accepted: BrF5
wrongValueDiagnostics
[
{
"value": "Br₅F",
"misconception": "you attached the count to the wrong element — penta- belongs to fluoride, so the 5 follows F",
"feedback": "This answer is wrong — you attached the count to the wrong element — penta- belongs to fluoride, so the 5 follows F."
},
{
"value": "BrF",
"misconception": "you dropped the count — penta- means the formula needs a 5 after F",
"feedback": "This answer is wrong — you dropped the count — penta- means the formula needs a 5 after F."
}
]
feedback
{
"keyExplanation": "Bromine has no prefix — one Br, no subscript. penta- means five, so F takes the subscript 5. Bromine pentafluoride is BrF₅.",
"anticipatedWrong": [
{
"value": "Br₅F",
"misconception": "you attached the count to the wrong element — penta- belongs to fluoride, so the 5 follows F",
"feedback": "This answer is wrong — you attached the count to the wrong element — penta- belongs to fluoride, so the 5 follows F."
},
{
"value": "BrF",
"misconception": "you dropped the count — penta- means the formula needs a 5 after F",
"feedback": "This answer is wrong — you dropped the count — penta- means the formula needs a 5 after F."
}
]
}
CMB-019 · medium · application · seq 15 · seed:U5-G1/pool[54] (CMB-019 gateItems) — CCl2F2 (019 article instance) -> SiHCl3 per ledger; 'None of the above' distractor REPLACED with the written-order misconception · mcq4
Which atom is the central atom of SiHCl₃, the industrial gas trichlorosilane?
Silicon KEY
Chlorine
Hydrogen
The molecule has no single central atom.
CMB-018 · medium · application · seq 16 · seed:U5-G1/pool[52] (CMB-018 gateItems) — BrCl (018 article instance) -> IBr per ledger; image-option format and error classes kept · mcq4
Which picture shows the correct Lewis diagram of IBr, iodine monobromide? Both of its elements come from Group 17.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "IBr",
"structure": "I–Br joined by one line; three dot pairs on the I and three dot pairs on the Br, drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "IBr (wrong)",
"structure": "I and Br symbols side by side with NO line between them; three dot pairs on the I; three dot pairs plus one extra dot pair on the Br (all 14 electrons drawn as dots)",
"style": "clean Lewis diagram, deliberately missing the bond line"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "IBr (wrong)",
"structure": "I–Br joined by one line; only TWO dot pairs on each atom (10 electrons drawn in total)",
"style": "clean Lewis diagram, deliberately short of lone pairs"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "IBr (wrong)",
"structure": "a circle labeled I⁺ and a separate circle labeled Br⁻ with a curved arrow showing one electron moved from I to Br — a transfer picture, no line, no shared dots",
"style": "particulate transfer diagram, deliberately the wrong representation"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-020 · hard · transfer · seq 17 · seed:U5-G1/pool[59] (CMB-020 gateItems) — CCl4 (020 article instance) -> GeCl4 per ledger; image-option format and error classes kept · mcq4
Which picture shows the correct Lewis diagram of germanium tetrachloride, GeCl₄? Germanium is a Group 14 element; chlorine is a Group 17 element.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "GeCl₄",
"structure": "Ge central, joined by one line to each of four Cl symbols; three dot pairs on each Cl, drawn radially; no dots on the Ge",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "GeCl₄ (wrong)",
"structure": "a Cl central, joined by lines to the Ge and the other three Cl symbols; three dot pairs on each outer atom",
"style": "clean Lewis diagram, deliberately wrong central atom"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "GeCl₄ (wrong)",
"structure": "Ge central with four lines to Cl symbols; TWO dot pairs on the Ge and two dot pairs on each Cl (28 electrons drawn)",
"style": "clean Lewis diagram, deliberately misplacing lone pairs on the central atom"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "GeCl₄ (wrong)",
"structure": "Ge central with four lines to Cl symbols; only TWO dot pairs on each Cl (24 electrons drawn in total)",
"style": "clean Lewis diagram, deliberately short of the 32-electron total"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-021 · hard · transfer · seq 18 · seed:U5-G1/pool[62] (CMB-021 gateItems) — VERBATIM (element-free); misconceptions authored · mcq4
A student is drawing a Lewis diagram. Every electron is placed as single bonds and lone pairs, yet the central atom sits at only six electrons. What should the student do next?
Move a lone pair from an outer atom into the bond, making a double bond. KEY
Add two more electrons to the central atom.
Move a lone pair from the central atom onto an outer atom.
Erase a lone pair from an outer atom and leave it out of the diagram.
CMB-009 · hard · transfer · seq 19 · seed:U5-G1/pool[24] = demo_curated[0] (james_curated, dedup — both refs) — Na3N (009 article instance) -> Mg3N2 per ledger; diagnostics re-keyed to the 2:3 charge balance · text
Name Mg₃N₂.
Answer: magnesium nitride KEY
also accepted: Magnesium nitride
wrongValueDiagnostics
[
{
"value": "trimagnesium dinitride",
"misconception": "you counted with prefixes — magnesium is a metal, so Mg₃N₂ is ionic, and ionic names never use prefixes",
"feedback": "This answer is wrong — you counted with prefixes — magnesium is a metal, so Mg₃N₂ is ionic, and ionic names never use prefixes."
},
{
"value": "magnesium(II) nitride",
"misconception": "you added a Roman numeral — magnesium forms only Mg²⁺, so no numeral is needed and none is written",
"feedback": "This answer is wrong — you added a Roman numeral — magnesium forms only Mg²⁺, so no numeral is needed and none is written."
}
]
feedback
{
"keyExplanation": "First element: magnesium, a metal — ionic naming, no prefixes. The subscripts come from the charges (three Mg²⁺ balance two N³⁻), so the name is simply magnesium nitride.",
"anticipatedWrong": [
{
"value": "trimagnesium dinitride",
"misconception": "you counted with prefixes — magnesium is a metal, so Mg₃N₂ is ionic, and ionic names never use prefixes",
"feedback": "This answer is wrong — you counted with prefixes — magnesium is a metal, so Mg₃N₂ is ionic, and ionic names never use prefixes."
},
{
"value": "magnesium(II) nitride",
"misconception": "you added a Roman numeral — magnesium forms only Mg²⁺, so no numeral is needed and none is written",
"feedback": "This answer is wrong — you added a Roman numeral — magnesium forms only Mg²⁺, so no numeral is needed and none is written."
}
]
}
CMB-022 · hard · transfer · seq 20 · seed:U5-G1/pool[63] (CMB-022 gateItems) — HOCl (022 article instance) -> HOBr per ledger; wrong-placement case kept (same 14-electron topology) · mcq4
The figure shows a student's Lewis diagram of HOBr. The correct total for HOBr is 14 electrons in all. Run the two checks. What is the verdict?
FIGURE (lewis-diagram · stimulus) — molecule: "HOBr (a student's wrong diagram)" · structure: "H–O–Br in a row with single lines; THREE radial lone pairs on the O; only TWO radial lone pairs on the Br" · style: "clean textbook Lewis diagram, deliberately wrong"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "HOBr (a student's wrong diagram)",
"structure": "H–O–Br in a row with single lines; THREE radial lone pairs on the O; only TWO radial lone pairs on the Br",
"style": "clean textbook Lewis diagram, deliberately wrong"
}
}
The total is right, but the second check fails. KEY
The diagram is correct.
The total number of electrons shown is too high.
The total number of electrons shown is too low.
CMB-023 · medium · application · seq 21 · seed:U5-G1/prod_seeds[6] (CMB-023 gate prod, = pool[66]/[67] family) — CH2Cl2 -> CHCl3 per ledger; routine and checklist structure kept · frq
Use the five-step routine to plan the Lewis diagram of chloroform, CHCl₃. Carbon is a Group 14 element, chlorine is a Group 17 element, and hydrogen carries one valence electron. Write your answer in the answer box:
FIGURE (model_answer_diagram · model_answer_diagram) — see raw specraw spec
{
"figureShape": "model_answer_diagram",
"modelAnswerFigureSpecs": {
"c": {
"figureType": "lewis-diagram",
"molecule": "CHCl₃",
"structure": "C central joined by single lines to one H and three Cl symbols; three radial lone pairs on each Cl; no dots on C or H",
"style": "clean textbook Lewis diagram"
}
}
}
Use the five-step routine to plan the Lewis diagram of chloroform, CHCl₃. Carbon is a Group 14 element, chlorine is a Group 17 element, and hydrogen carries one valence electron. Write your answer in the answer box:
(a) State the total number of valence electrons, showing the count for each element.
(b) Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
(c) Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and every atom reaches its target: eight, or two for a hydrogen atom.
Part a. State the total number of valence electrons, showing the count for each element.
Part b. Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
Model: Carbon is the central atom because it can form the most bonds — four, while hydrogen and chlorine each form one. The skeleton is the carbon in the middle joined by single lines to the hydrogen and to each of the three chlorines: four lines, using 8 of the 26 electrons.
Part c. Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and every atom reaches its target: eight, or two for a hydrogen atom.
Model: The remaining 18 electrons sit as three lone pairs on each chlorine, pointing straight out with the dots side by side; the carbon and the hydrogen carry no dots. Check 1: four lines (8) plus nine lone pairs (18) = 26 electrons drawn, matching the total. Check 2: the carbon counts its four shared pairs = 8; each chlorine counts one shared pair plus three lone pairs = 8; the hydrogen counts its one shared pair = 2. Both checks pass, so step 5 (conversion) is not needed.
Full model answer. (a) carbon: 1 atom × 4 valence electrons = 4; hydrogen: 1 atom × 1 = 1; chlorine: 3 atoms × 7 = 21. Total = 4 + 1 + 21 = 26 valence electrons.
(b) Carbon is the central atom because it can form the most bonds — four, while hydrogen and chlorine each form one. The skeleton is the carbon in the middle joined by single lines to the hydrogen and to each of the three chlorines: four lines, using 8 of the 26 electrons.
(c) The remaining 18 electrons sit as three lone pairs on each chlorine, pointing straight out with the dots side by side; the carbon and the hydrogen carry no dots. Check 1: four lines (8) plus nine lone pairs (18) = 26 electrons drawn, matching the total. Check 2: the carbon counts its four shared pairs = 8; each chlorine counts one shared pair plus three lone pairs = 8; the hydrogen counts its one shared pair = 2. Both checks pass, so step 5 (conversion) is not needed.
Sucrose — table sugar — is built of separate, neutral C₁₂H₂₂O₁₁ units, each a bound group of atoms with no charges anywhere. What kind of substance is sucrose?
A molecular substance. KEY
An ionic compound.
A metallic substance.
An element.
CMB-010 · easy · recall · seq 2 · AUTHORED (line-meaning facet of the taught code; element-free) · mcq4
In any Lewis diagram, what does a straight line drawn between two element symbols stand for?
One shared pair — two electrons held by both atoms at once. KEY
One single electron shared between the two atoms.
Two electrons that belong entirely to one of the two atoms.
An electron that has moved from one atom to the other.
Butane has the molecular formula C₄H₁₀. How many atoms in total does one butane molecule contain?
Answer: 14 atoms KEY
also accepted: 14 atoms, 14.0
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted the elements, not the atoms — add the two subscripts: 4 + 10",
"feedback": "This answer is wrong — you counted the elements, not the atoms — add the two subscripts: 4 + 10."
},
{
"value": 10,
"misconception": "you took the largest subscript as the total — every element's count joins the sum",
"feedback": "This answer is wrong — you took the largest subscript as the total — every element's count joins the sum."
},
{
"value": 4,
"misconception": "you read only the first subscript — the 10 hydrogens count too",
"feedback": "This answer is wrong — you read only the first subscript — the 10 hydrogens count too."
}
]
feedback
{
"keyExplanation": "Each subscript counts its own element: 4 carbon and 10 hydrogen. The total is 4 + 10 = 14 atoms in one butane molecule.",
"anticipatedWrong": [
{
"value": 2,
"misconception": "you counted the elements, not the atoms — add the two subscripts: 4 + 10",
"feedback": "This answer is wrong — you counted the elements, not the atoms — add the two subscripts: 4 + 10."
},
{
"value": 10,
"misconception": "you took the largest subscript as the total — every element's count joins the sum",
"feedback": "This answer is wrong — you took the largest subscript as the total — every element's count joins the sum."
},
{
"value": 4,
"misconception": "you read only the first subscript — the 10 hydrogens count too",
"feedback": "This answer is wrong — you read only the first subscript — the 10 hydrogens count too."
}
]
}
CMB-001 · medium · application · seq 5 · AUTHORED to the seed pattern (panel order flipped: sharing first); Cs->Cl / P-H per ledger · mcq4
Diagrams 1 and 2 in the figure each show one two-atom pairing. Which classification is correct?
FIGURE (particulate-bond-panels · stimulus) — panels: [{"panel": "1", "description": "a larger circle labeled P overlapping a smaller circle labeled H, with two dots in the overlap region"}, {"panel": "2", "desc… · style: "clean textbook particulate diagrams, boxed panels"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "particulate-bond-panels",
"panels": [
{
"panel": "1",
"description": "a larger circle labeled P overlapping a smaller circle labeled H, with two dots in the overlap region"
},
{
"panel": "2",
"description": "a circle labeled Cs⁺ and a separate circle labeled Cl⁻, with a curved arrow showing one electron moved from Cs to Cl"
}
],
"style": "clean textbook particulate diagrams, boxed panels"
}
}
Diagram 1 shows sharing, and diagram 2 shows transfer. KEY
Diagram 1 shows transfer, and diagram 2 shows sharing.
Two atoms share one pair of electrons. Why do the two atoms stay together?
Both nuclei attract the same shared electrons, which pulls the two atoms together. KEY
Each atom's outer shell is full, and full shells lock the atoms in place.
One atom has taken the other's electron, and the opposite charges attract.
The overlapping of the two atoms' shells sticks them together on contact.
CMB-011 · medium · application · seq 8 · seed:U5-G1/pool[31] (CMB-011 gateItems) — NF3 (011 article instance) -> GeF4 per ledger -> OF2 (QC wave 2) -> CH2F2 (packaging sweep: OF2 is student-practiced in CMB-015/CMB-017 fluency + CMB-020 production; CH2F2's only unit presence is out-of-scope CMB-028); count-trap structure kept · mcq4
How many lone pairs does the whole Lewis diagram of CH₂F₂ shown in the figure contain?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₂F₂" · structure: "C central, joined by one line to each of two H symbols and one line to each of two F symbols; three dot pairs on each F, drawn radially; no dots on the C or… · style: "clean Lewis diagram; lone pairs radial, dots equidistant"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₂F₂",
"structure": "C central, joined by one line to each of two H symbols and one line to each of two F symbols; three dot pairs on each F, drawn radially; no dots on the C or the H symbols",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
}
The figure shows the Lewis diagram of 1-butene, C₄H₈, with the three bonds along the chain labeled 1, 2, and 3. Which statement classifies bonds 1, 2, and 3?
FIGURE (lewis-diagram · stimulus) — molecule: "C₄H₈" · structure: "a four-atom chain: two lines between the first and second chain atoms labeled 1, one line between the second and third labeled 2, one line between the third… · style: "clean Lewis diagram; bond labels as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₄H₈",
"structure": "a four-atom chain: two lines between the first and second chain atoms labeled 1, one line between the second and third labeled 2, one line between the third and fourth labeled 3; H atoms joined by single lines so the chain atoms carry 2, 1, 2, and 3 hydrogens in order; no dots anywhere",
"style": "clean Lewis diagram; bond labels as small numbered arrows"
}
}
Bond 1 is a double bond; bonds 2 and 3 are single bonds. KEY
All three bonds are single bonds.
All three bonds are double bonds.
Bond 1 is a triple bond; bonds 2 and 3 are single bonds.
The figure shows the Lewis diagram of disilane, Si₂H₆. How many electrons surround the left silicon atom?
FIGURE (lewis-diagram · stimulus) — molecule: "Si₂H₆" · structure: "two Si symbols joined by one line; each Si also joined by single lines to three H symbols; no dots anywhere" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "Si₂H₆",
"structure": "two Si symbols joined by one line; each Si also joined by single lines to three H symbols; no dots anywhere",
"style": "clean textbook Lewis diagram"
}
}
Answer: 8 electrons KEY
also accepted: 8 electrons, 8.0
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the lines, not the electrons — each of the four lines is a pair of two electrons",
"feedback": "This answer is wrong — you counted the lines, not the electrons — each of the four lines is a pair of two electrons."
},
{
"value": 6,
"misconception": "you skipped the silicon–silicon bond — its shared pair surrounds the left silicon too",
"feedback": "This answer is wrong — you skipped the silicon–silicon bond — its shared pair surrounds the left silicon too."
},
{
"value": 14,
"misconception": "you counted every electron in the diagram — count only the pairs touching the left silicon",
"feedback": "This answer is wrong — you counted every electron in the diagram — count only the pairs touching the left silicon."
}
]
feedback
{
"keyExplanation": "Four lines touch the left silicon: three Si–H bonds and the Si–Si bond. Each line is one shared pair of two electrons: 4 × 2 = 8 electrons surround the left silicon.",
"anticipatedWrong": [
{
"value": 4,
"misconception": "you counted the lines, not the electrons — each of the four lines is a pair of two electrons",
"feedback": "This answer is wrong — you counted the lines, not the electrons — each of the four lines is a pair of two electrons."
},
{
"value": 6,
"misconception": "you skipped the silicon–silicon bond — its shared pair surrounds the left silicon too",
"feedback": "This answer is wrong — you skipped the silicon–silicon bond — its shared pair surrounds the left silicon too."
},
{
"value": 14,
"misconception": "you counted every electron in the diagram — count only the pairs touching the left silicon",
"feedback": "This answer is wrong — you counted every electron in the diagram — count only the pairs touching the left silicon."
}
]
}
CMB-016 · medium · application · seq 11 · seed:U5-G1/pool[46] (CMB-016 gateItems) — nitrogen/hydrogen case ANONYMIZED per ledger (element E + one-bond partner J); partner-chain logic kept · numeric
In one molecule, an atom of element E bonds only to atoms of element J, and each J atom forms exactly one bond. An E atom has five valence electrons, and every atom reaches its typical bond count. How many J atoms does the E atom bond to?
Answer: 3 atoms KEY
also accepted: 3 atoms, 3.0
scaffold
[
"Write down the values in the question:",
"valence electrons of E = 5",
"Write down the relationship:",
"typical bonds = 8 − valence electrons",
"Substitute in the values, and calculate:",
"typical bonds = 8 − 5 = 3",
"Each J atom forms one bond, so three bonds means 3 J atoms."
]
wrongValueDiagnostics
[
{
"value": 5,
"misconception": "you used E's valence count as the number of partners — the partners equal the bonds, which is 8 − 5",
"feedback": "This answer is wrong — you used E's valence count as the number of partners — the partners equal the bonds, which is 8 − 5."
},
{
"value": 8,
"misconception": "you used the full octet count as the number of partners — eight is the electron target, not the bond count",
"feedback": "This answer is wrong — you used the full octet count as the number of partners — eight is the electron target, not the bond count."
},
{
"value": 1,
"misconception": "you assumed E, like its partner, forms just one bond — E needs three more electrons, so it forms three bonds",
"feedback": "This answer is wrong — you assumed E, like its partner, forms just one bond — E needs three more electrons, so it forms three bonds."
}
]
feedback
{
"keyExplanation": "E typically forms 8 − 5 = 3 bonds. Each J atom forms one bond, so each bond uses one J atom. Three bonds means three J atoms.",
"anticipatedWrong": [
{
"value": 5,
"misconception": "you used E's valence count as the number of partners — the partners equal the bonds, which is 8 − 5",
"feedback": "This answer is wrong — you used E's valence count as the number of partners — the partners equal the bonds, which is 8 − 5."
},
{
"value": 8,
"misconception": "you used the full octet count as the number of partners — eight is the electron target, not the bond count",
"feedback": "This answer is wrong — you used the full octet count as the number of partners — eight is the electron target, not the bond count."
},
{
"value": 1,
"misconception": "you assumed E, like its partner, forms just one bond — E needs three more electrons, so it forms three bonds",
"feedback": "This answer is wrong — you assumed E, like its partner, forms just one bond — E needs three more electrons, so it forms three bonds."
}
]
}
CMB-017 · medium · application · seq 12 · seed:U5-G1/pool[49] (CMB-017 gateItems) — C2H6/14 -> BI3/24 per stage-2 patched ledger (the CH2F2 draft kept carbon/hydrogen/fluorine, all own-lesson 017 materials); trap set kept · numeric
Boron has three valence electrons, and iodine belongs to Group 17. In one BI₃ molecule, what is the total number of valence electrons?
Answer: 24 valence electrons KEY
also accepted: 24 valence electrons, 24 electrons, 24.0
scaffold
[
"Write down the values in the question:",
"boron: 1 atom × 3 valence electrons",
"iodine: 3 atoms × 7 valence electrons",
"Write down the relationship:",
"total valence electrons = the sum over every element of (atoms × valence electrons)",
"Substitute in the values, and calculate:",
"total valence electrons = 3 + 21 = 24"
]
wrongValueDiagnostics
[
{
"value": 10,
"misconception": "you counted one iodine — the subscript 3 means three iodine atoms",
"feedback": "This answer is wrong — you counted one iodine — the subscript 3 means three iodine atoms."
},
{
"value": 54,
"misconception": "you used iodine's group number 17 as its valence count — Group 17 atoms have seven valence electrons",
"feedback": "This answer is wrong — you used iodine's group number 17 as its valence count — Group 17 atoms have seven valence electrons."
},
{
"value": 4,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
feedback
{
"keyExplanation": "boron: 1 atom × 3 valence electrons\niodine: 3 atoms × 7 valence electrons\ntotal valence electrons = (1 × 3) + (3 × 7) = 3 + 21 = 24",
"anticipatedWrong": [
{
"value": 10,
"misconception": "you counted one iodine — the subscript 3 means three iodine atoms",
"feedback": "This answer is wrong — you counted one iodine — the subscript 3 means three iodine atoms."
},
{
"value": 54,
"misconception": "you used iodine's group number 17 as its valence count — Group 17 atoms have seven valence electrons",
"feedback": "This answer is wrong — you used iodine's group number 17 as its valence count — Group 17 atoms have seven valence electrons."
},
{
"value": 4,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
}
CMB-007 · medium · application · seq 13 · seed:U5-G1/pool[19] (CMB-007 gateItems) — CS2 (007 article instance) -> S2Cl2 per ledger; the mono-drop teaching becomes a di-on-first-element case, diagnostics re-keyed · text
Name the binary molecular compound S₂Cl₂.
Answer: disulfur dichloride KEY
also accepted: disulphur dichloride, Disulfur dichloride
wrongValueDiagnostics
[
{
"value": "sulfur dichloride",
"misconception": "you dropped di- from the first element — only mono- is ever dropped; two sulfurs need di-",
"feedback": "This answer is wrong — you dropped di- from the first element — only mono- is ever dropped; two sulfurs need di-."
},
{
"value": "disulfur chloride",
"misconception": "you left the two chlorines uncounted — the second element needs di- too",
"feedback": "This answer is wrong — you left the two chlorines uncounted — the second element needs di- too."
},
{
"value": "disulfur dichlorine",
"misconception": "you skipped the -ide ending — the second element's ending changes to -ide",
"feedback": "This answer is wrong — you skipped the -ide ending — the second element's ending changes to -ide."
}
]
feedback
{
"keyExplanation": "Two sulfurs take di- (a prefix other than mono- is never dropped, even on the first element), and two chlorines take di- with the -ide ending. S₂Cl₂ is disulfur dichloride.",
"anticipatedWrong": [
{
"value": "sulfur dichloride",
"misconception": "you dropped di- from the first element — only mono- is ever dropped; two sulfurs need di-",
"feedback": "This answer is wrong — you dropped di- from the first element — only mono- is ever dropped; two sulfurs need di-."
},
{
"value": "disulfur chloride",
"misconception": "you left the two chlorines uncounted — the second element needs di- too",
"feedback": "This answer is wrong — you left the two chlorines uncounted — the second element needs di- too."
},
{
"value": "disulfur dichlorine",
"misconception": "you skipped the -ide ending — the second element's ending changes to -ide",
"feedback": "This answer is wrong — you skipped the -ide ending — the second element's ending changes to -ide."
}
]
}
CMB-008 · medium · application · seq 14 · seed:U5-G1/pool[22] (CMB-008 gateItems) — P4O10 (008 article instance) -> IF7 per ledger; the deca- decode moves to form D, diagnostics re-keyed to hepta- · text
Write the formula of iodine heptafluoride.
Answer: IF₇ KEY
also accepted: IF7
wrongValueDiagnostics
[
{
"value": "I₇F",
"misconception": "you attached the count to the wrong element — hepta- belongs to fluoride, so the 7 follows F",
"feedback": "This answer is wrong — you attached the count to the wrong element — hepta- belongs to fluoride, so the 7 follows F."
},
{
"value": "IF₆",
"misconception": "you slid one prefix down — hexa- is 6; hepta- is 7",
"feedback": "This answer is wrong — you slid one prefix down — hexa- is 6; hepta- is 7."
}
]
feedback
{
"keyExplanation": "Iodine has no prefix — one I, no subscript. hepta- means seven, so F takes the subscript 7. Iodine heptafluoride is IF₇.",
"anticipatedWrong": [
{
"value": "I₇F",
"misconception": "you attached the count to the wrong element — hepta- belongs to fluoride, so the 7 follows F",
"feedback": "This answer is wrong — you attached the count to the wrong element — hepta- belongs to fluoride, so the 7 follows F."
},
{
"value": "IF₆",
"misconception": "you slid one prefix down — hexa- is 6; hepta- is 7",
"feedback": "This answer is wrong — you slid one prefix down — hexa- is 6; hepta- is 7."
}
]
}
A student picks hydrogen as the central atom of H₂Te, saying there are two hydrogens and they are written first. Why is the student wrong?
Hydrogen forms only one bond, and a central atom must bond to more than one atom. KEY
Tellurium is heavier than hydrogen, and the heavier atom takes the center.
The central atom is whichever element the formula names last.
The central atom is the element with the most atoms in the formula.
CMB-018 · medium · application · seq 16 · AUTHORED to the seed pattern (BrF per ledger) · mcq4
Which picture shows the correct Lewis diagram of BrF, bromine monofluoride? Both of its elements belong to Group 17.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "BrF",
"structure": "Br–F joined by one line; three dot pairs on the Br and three dot pairs on the F, drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "BrF (wrong)",
"structure": "Br–F joined by one line; only TWO dot pairs on each atom (10 electrons drawn in total)",
"style": "clean Lewis diagram, deliberately short of lone pairs"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "BrF (wrong)",
"structure": "Br and F symbols side by side with NO line; three dot pairs on the F, four dot pairs on the Br (all 14 electrons as dots)",
"style": "clean Lewis diagram, deliberately missing the bond line"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "BrF (wrong)",
"structure": "Br=F joined by two parallel lines; two dot pairs on the Br and three dot pairs on the F",
"style": "clean Lewis diagram, deliberately over-bonded"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-020 · hard · transfer · seq 17 · AUTHORED to the seed pattern (CH3I per ledger) · mcq4
Which picture shows the correct Lewis diagram of CH₃I? Carbon belongs to Group 14, hydrogen supplies one valence electron apiece, and iodine belongs to Group 17.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃I",
"structure": "C central, joined by single lines to three H symbols and to I; three dot pairs on the I, drawn radially; no dots on C or H",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃I (wrong)",
"structure": "C central with lines to three H and to I; one dot pair on each H and one dot pair on the I",
"style": "clean Lewis diagram, deliberately putting dots on hydrogens"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃I (wrong)",
"structure": "I central, joined by lines to the C and the three H symbols; three dot pairs on the C",
"style": "clean Lewis diagram, deliberately wrong central atom"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃I (wrong)",
"structure": "C central with lines to three H and to I; only TWO dot pairs on the I (12 electrons drawn)",
"style": "clean Lewis diagram, deliberately short of the total"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-021 · hard · transfer · seq 18 · AUTHORED (what-conversion-changes facet, element-free) · mcq4
While finishing a Lewis diagram, a student converts a lone pair on an outer atom into a second shared pair with the central atom. What happens to the electron counts?
The central atom gains two, and the diagram's total stays the same. KEY
The diagram's total number of electrons rises by two.
The outer atom drops to six electrons.
Both atoms gain two electrons each, so the total rises by four.
CMB-009 · hard · transfer · seq 19 · seed:U5-G1/pool[25] = demo_curated[1] (james_curated, dedup — both refs) — ClF3 (009 article instance) -> BCl3 per ledger; diagnostics kept · text
Name SO₂.
Answer: sulfur dioxide KEY
also accepted: Sulfur dioxide, sulphur dioxide
wrongValueDiagnostics
[
{
"value": "sulfur oxide",
"misconception": "you skipped the count — two oxygens need di-",
"feedback": "This answer is wrong — you skipped the count — two oxygens need di-."
},
{
"value": "monosulfur dioxide",
"misconception": "you kept mono- on the first element — mono- is always dropped there",
"feedback": "This answer is wrong — you kept mono- on the first element — mono- is always dropped there."
},
{
"value": "disulfur oxide",
"misconception": "you attached the prefix to the wrong element — each prefix counts the element it sits in front of",
"feedback": "This answer is wrong — you attached the prefix to the wrong element — each prefix counts the element it sits in front of."
}
]
feedback
{
"keyExplanation": "Sulfur and oxygen are both nonmetals, so SO₂ takes prefix naming: one sulfur keeps no prefix (mono- is dropped on the first element), and two oxygens take di- with the -ide ending — sulfur dioxide.",
"anticipatedWrong": [
{
"value": "sulfur oxide",
"misconception": "you skipped the count — two oxygens need di-",
"feedback": "This answer is wrong — you skipped the count — two oxygens need di-."
},
{
"value": "monosulfur dioxide",
"misconception": "you kept mono- on the first element — mono- is always dropped there",
"feedback": "This answer is wrong — you kept mono- on the first element — mono- is always dropped there."
},
{
"value": "disulfur oxide",
"misconception": "you attached the prefix to the wrong element — each prefix counts the element it sits in front of",
"feedback": "This answer is wrong — you attached the prefix to the wrong element — each prefix counts the element it sits in front of."
}
]
}
CMB-022 · hard · transfer · seq 20 · seed:U5-G1/pool[64] (CMB-022 gateItems) — CO2 (022 article instance) -> carbon diselenide CSe2 per ledger (obscure-but-real flagged; the figure carries the drawn structure); starving-carbon case kept · mcq4
The figure shows a student's Lewis diagram of CSe₂, carbon diselenide. The total electron count of 16 is correct. Which atom, if any, fails the second check?
FIGURE (lewis-diagram · stimulus) — molecule: "CSe₂ (a student's wrong diagram)" · structure: "Se–C–Se with SINGLE lines; three radial lone pairs on each Se; no dots on the C" · style: "clean textbook Lewis diagram, deliberately wrong"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CSe₂ (a student's wrong diagram)",
"structure": "Se–C–Se with SINGLE lines; three radial lone pairs on each Se; no dots on the C",
"style": "clean textbook Lewis diagram, deliberately wrong"
}
}
Use the five-step routine to plan the Lewis diagram of silicon tetrabromide, SiBr₄. Silicon belongs to Group 14 and bromine belongs to Group 17. Show your plan in the answer box:
FIGURE (model_answer_diagram · model_answer_diagram) — see raw specraw spec
{
"figureShape": "model_answer_diagram",
"modelAnswerFigureSpecs": {
"c": {
"figureType": "lewis-diagram",
"molecule": "SiBr₄",
"structure": "Si central joined by single lines to four Br symbols; three radial lone pairs on each Br; no dots on Si",
"style": "clean textbook Lewis diagram"
}
}
}
Use the five-step routine to plan the Lewis diagram of silicon tetrabromide, SiBr₄. Silicon belongs to Group 14 and bromine belongs to Group 17. Show your plan in the answer box:
(a) State the total number of valence electrons, showing the count for each element.
(b) Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
(c) Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and every atom reaches eight.
Part a. State the total number of valence electrons, showing the count for each element.
Part b. Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
Model: Silicon is the central atom because it can form the most bonds — four, while bromine forms one. The skeleton is the silicon in the middle joined by a single line to each of the four bromines: four lines, using 8 of the 32 electrons.
Part c. Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and every atom reaches eight.
Model: The remaining 24 electrons sit as three lone pairs on each bromine, pointing straight out with the dots side by side; the silicon carries no dots. Check 1: four lines (8) plus twelve lone pairs (24) = 32 electrons drawn, matching the total. Check 2: the silicon counts its four shared pairs = 8; each bromine counts one shared pair plus three lone pairs = 8. Both checks pass, so step 5 (conversion) is not needed.
Full model answer. (a) silicon: 1 atom × 4 valence electrons = 4; bromine: 4 atoms × 7 = 28. Total = 4 + 28 = 32 valence electrons.
(b) Silicon is the central atom because it can form the most bonds — four, while bromine forms one. The skeleton is the silicon in the middle joined by a single line to each of the four bromines: four lines, using 8 of the 32 electrons.
(c) The remaining 24 electrons sit as three lone pairs on each bromine, pointing straight out with the dots side by side; the silicon carries no dots. Check 1: four lines (8) plus twelve lone pairs (24) = 32 electrons drawn, matching the total. Check 2: the silicon counts its four shared pairs = 8; each bromine counts one shared pair plus three lone pairs = 8. Both checks pass, so step 5 (conversion) is not needed.
Hydrogen atoms in molecules are surrounded by two electrons, not eight. Which noble gas has the electron count that hydrogen's two matches?
Helium KEY
Neon
Argon
No noble gas — hydrogen sits outside the pattern entirely.
CMB-005 · easy · application · seq 4 · AUTHORED (element-count facet; BBr3 per stage-2 patched ledger — the acetaldehyde draft kept 'carbon', an own-lesson 005 material; formula-reading only, no Lewis claim on the electron-poor boron) · numeric
Count the bromine atoms in one molecule of BBr₃.
Answer: 3 atoms KEY
also accepted: 3 atoms, 3.0
wrongValueDiagnostics
[
{
"value": 1,
"misconception": "you read the first element's count — the subscript 3 sits after Br, so it counts bromine",
"feedback": "This answer is wrong — you read the first element's count — the subscript 3 sits after Br, so it counts bromine."
},
{
"value": 4,
"misconception": "you counted every atom in the molecule — the question asks for the bromine atoms alone",
"feedback": "This answer is wrong — you counted every atom in the molecule — the question asks for the bromine atoms alone."
}
]
feedback
{
"keyExplanation": "The subscript after Br is 3, so one BBr₃ molecule contains 3 bromine atoms. The boron, with no subscript, counts as one atom — but it is not bromine.",
"anticipatedWrong": [
{
"value": 1,
"misconception": "you read the first element's count — the subscript 3 sits after Br, so it counts bromine",
"feedback": "This answer is wrong — you read the first element's count — the subscript 3 sits after Br, so it counts bromine."
},
{
"value": 4,
"misconception": "you counted every atom in the molecule — the question asks for the bromine atoms alone",
"feedback": "This answer is wrong — you counted every atom in the molecule — the question asks for the bromine atoms alone."
}
]
}
CMB-001 · medium · application · seq 5 · AUTHORED to the seed pattern; Sr->S / I-F per ledger · mcq4
Each of diagrams 1 and 2 in the figure shows a single two-atom bond. Which classification is correct?
FIGURE (particulate-bond-panels · stimulus) — panels: [{"panel": "1", "description": "a circle labeled Sr²⁺ and a separate circle labeled S²⁻, with a curved arrow showing two electrons moved from Sr to S"}, {"pa… · style: "clean textbook particulate diagrams, boxed panels"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "particulate-bond-panels",
"panels": [
{
"panel": "1",
"description": "a circle labeled Sr²⁺ and a separate circle labeled S²⁻, with a curved arrow showing two electrons moved from Sr to S"
},
{
"panel": "2",
"description": "a larger circle labeled I overlapping a smaller circle labeled F, with two dots in the overlap region"
}
],
"style": "clean textbook particulate diagrams, boxed panels"
}
}
Diagram 1 shows transfer, and diagram 2 shows sharing. KEY
Diagram 1 shows sharing, and diagram 2 shows transfer.
Four bonds are described. Bond 1: one electron moves completely from atom A onto atom D. Bond 2: atoms E and G hold one shared pair of electrons between them. Bond 3: two electrons move completely from atom J onto atom L. Bond 4: one electron moves completely from atom Q onto atom R. Which bond is covalent?
Two atoms of the same element share three pairs of electrons. Which statement explains why the atoms stay together?
Both nuclei attract the same shared electrons, which pulls the two atoms together. KEY
Each nucleus attracts only the electrons it originally contributed.
The two atoms carry opposite whole charges that attract.
Wanting a full outer shell pulls each atom toward the other.
CMB-011 · medium · application · seq 8 · AUTHORED (classify facet on methylamine CH3NH2 per ledger; seed pool[30] pattern) · mcq4
The figure shows the Lewis diagram of methylamine, CH₃NH₂, with tags 1 and 2 on two of its electron pairs. Which classification is correct?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃NH₂" · structure: "C joined by single lines to three H symbols and to N; N joined by single lines to two H symbols; one dot pair on the N drawn radially; the C–N line labeled … · style: "clean Lewis diagram; lone pairs radial, dots equidistant; pair markers as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃NH₂",
"structure": "C joined by single lines to three H symbols and to N; N joined by single lines to two H symbols; one dot pair on the N drawn radially; the C–N line labeled 1, the dot pair on N labeled 2",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant; pair markers as small numbered arrows"
}
}
Pair 1 is a bonding pair, and pair 2 is a lone pair. KEY
Pair 1 is a lone pair, and pair 2 is a bonding pair.
Both pairs are bonding pairs.
Neither pair is a bonding pair, because the marked line touches two different elements.
The figure shows the Lewis diagram of diimide, N₂H₂, with the bond between the two middle atoms labeled 1. Classify bond 1.
FIGURE (lewis-diagram · stimulus) — molecule: "N₂H₂" · structure: "an H-N=N-H chain: one line between each H and its neighbor, two lines between the two middle symbols labeled 1, one dot pair on each middle atom drawn radia… · style: "clean Lewis diagram; lone pairs radial, dots equidistant; bond labels as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "N₂H₂",
"structure": "an H-N=N-H chain: one line between each H and its neighbor, two lines between the two middle symbols labeled 1, one dot pair on each middle atom drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant; bond labels as small numbered arrows"
}
}
A double bond. KEY
A single bond.
A triple bond.
Two single bonds.
CMB-015 · medium · application · seq 10 · AUTHORED (triple-bond counting facet on propyne C3H4 per ledger — the seed family's triple facet relocated here, drift recorded) · numeric
The figure shows the Lewis diagram of propyne, C₃H₄. How many electrons surround the middle atom of the chain?
FIGURE (lewis-diagram · stimulus) — molecule: "C₃H₄" · structure: "a three-carbon row: the first C joined by single lines to three H symbols and by one line to the middle C; three lines between the middle C and the third C;… · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₃H₄",
"structure": "a three-carbon row: the first C joined by single lines to three H symbols and by one line to the middle C; three lines between the middle C and the third C; one line between the third C and its H; no dots anywhere",
"style": "clean textbook Lewis diagram"
}
}
Answer: 8 electrons KEY
also accepted: 8 electrons, 8.0
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the triple bond as one shared pair — a triple bond is three shared pairs, six electrons",
"feedback": "This answer is wrong — you counted the triple bond as one shared pair — a triple bond is three shared pairs, six electrons."
},
{
"value": 6,
"misconception": "you stopped at the triple bond — the single bond's shared pair also surrounds the middle carbon",
"feedback": "This answer is wrong — you stopped at the triple bond — the single bond's shared pair also surrounds the middle carbon."
},
{
"value": 16,
"misconception": "you counted every electron in the diagram — count only the pairs touching the middle carbon",
"feedback": "This answer is wrong — you counted every electron in the diagram — count only the pairs touching the middle carbon."
}
]
feedback
{
"keyExplanation": "The triple bond is three shared pairs: 6 electrons. The single bond to the neighboring carbon adds one more pair: 2 electrons. 6 + 2 = 8 electrons surround the middle carbon.",
"anticipatedWrong": [
{
"value": 4,
"misconception": "you counted the triple bond as one shared pair — a triple bond is three shared pairs, six electrons",
"feedback": "This answer is wrong — you counted the triple bond as one shared pair — a triple bond is three shared pairs, six electrons."
},
{
"value": 6,
"misconception": "you stopped at the triple bond — the single bond's shared pair also surrounds the middle carbon",
"feedback": "This answer is wrong — you stopped at the triple bond — the single bond's shared pair also surrounds the middle carbon."
},
{
"value": 16,
"misconception": "you counted every electron in the diagram — count only the pairs touching the middle carbon",
"feedback": "This answer is wrong — you counted every electron in the diagram — count only the pairs touching the middle carbon."
}
]
}
CMB-016 · medium · application · seq 11 · AUTHORED (anonymous 4-valence case; stage-2 patch: the drafted 7-valence case answered 1, which V-T6 bans as a bare power of ten) · numeric
An atom of element Q has four valence electrons. How many covalent bonds does Q typically form?
Answer: 4 bonds KEY
also accepted: 4 bonds, 4.0
scaffold
[
"Write down the values in the question:",
"valence electrons = 4",
"Write down the relationship:",
"typical bonds = 8 − valence electrons",
"Substitute in the values, and calculate:",
"typical bonds = 8 − 4",
"typical bonds = 4"
]
wrongValueDiagnostics
[
{
"value": 8,
"misconception": "you answered with the octet target — eight is the electron goal, not the number of bonds",
"feedback": "This answer is wrong — you answered with the octet target — eight is the electron goal, not the number of bonds."
},
{
"value": 12,
"misconception": "you added the valence count to eight — the relationship subtracts it: bonds = 8 − 4",
"feedback": "This answer is wrong — you added the valence count to eight — the relationship subtracts it: bonds = 8 − 4."
}
]
feedback
{
"keyExplanation": "Write down the values in the question:\nvalence electrons = 4\nWrite down the relationship:\ntypical bonds = 8 − valence electrons\nSubstitute in the values, and calculate:\ntypical bonds = 8 − 4\ntypical bonds = 4",
"anticipatedWrong": [
{
"value": 8,
"misconception": "you answered with the octet target — eight is the electron goal, not the number of bonds",
"feedback": "This answer is wrong — you answered with the octet target — eight is the electron goal, not the number of bonds."
},
{
"value": 12,
"misconception": "you added the valence count to eight — the relationship subtracts it: bonds = 8 − 4",
"feedback": "This answer is wrong — you added the valence count to eight — the relationship subtracts it: bonds = 8 − 4."
}
]
}
CMB-017 · medium · application · seq 12 · seed:U5-G1/pool[50] (CMB-017 gateItems) — HCN and its 10 (017 article instances) -> GeH4 = 8 per ledger; trap set kept · numeric
The periodic table places germanium in Group 14; each hydrogen atom brings one valence electron. Work out the total number of valence electrons in one GeH₄ molecule.
Answer: 8 valence electrons KEY
also accepted: 8 valence electrons, 8 electrons, 8.0
scaffold
[
"Write down the values in the question:",
"germanium: 1 atom × 4 valence electrons",
"hydrogen: 4 atoms × 1 valence electron",
"Write down the relationship:",
"total valence electrons = the sum over every element of (atoms × valence electrons)",
"Substitute in the values, and calculate:",
"total valence electrons = 4 + 4 = 8"
]
wrongValueDiagnostics
[
{
"value": 5,
"misconception": "you counted one hydrogen — the subscript 4 means four hydrogen atoms",
"feedback": "This answer is wrong — you counted one hydrogen — the subscript 4 means four hydrogen atoms."
},
{
"value": 18,
"misconception": "you used the group number 14 as germanium's valence count — Group 14 atoms have four valence electrons",
"feedback": "This answer is wrong — you used the group number 14 as germanium's valence count — Group 14 atoms have four valence electrons."
},
{
"value": 40,
"misconception": "you gave every atom eight electrons — count each atom's own valence electrons instead",
"feedback": "This answer is wrong — you gave every atom eight electrons — count each atom's own valence electrons instead."
}
]
feedback
{
"keyExplanation": "germanium: 1 atom × 4 valence electrons\nhydrogen: 4 atoms × 1 valence electron\ntotal valence electrons = 4 + 4 = 8",
"anticipatedWrong": [
{
"value": 5,
"misconception": "you counted one hydrogen — the subscript 4 means four hydrogen atoms",
"feedback": "This answer is wrong — you counted one hydrogen — the subscript 4 means four hydrogen atoms."
},
{
"value": 18,
"misconception": "you used the group number 14 as germanium's valence count — Group 14 atoms have four valence electrons",
"feedback": "This answer is wrong — you used the group number 14 as germanium's valence count — Group 14 atoms have four valence electrons."
},
{
"value": 40,
"misconception": "you gave every atom eight electrons — count each atom's own valence electrons instead",
"feedback": "This answer is wrong — you gave every atom eight electrons — count each atom's own valence electrons instead."
}
]
}
CMB-007 · medium · application · seq 13 · AUTHORED (SiS2 per ledger -> Cl2O QC wave 2 -> SeF4 packaging sweep: Cl2O is WE-taught in CMB-008 + CMB-019 articles; SeF4 has zero unit presence; facet = mono- dropped on first element) · text
Name the binary molecular compound SeF₄.
Answer: selenium tetrafluoride KEY
also accepted: Selenium tetrafluoride
wrongValueDiagnostics
[
{
"value": "monoselenium tetrafluoride",
"misconception": "you added mono- to the first element — mono- is always dropped on the first element",
"feedback": "This answer is wrong — you added mono- to the first element — mono- is always dropped on the first element."
},
{
"value": "selenium fluoride",
"misconception": "you dropped the tetra- count from the second element — the prefix must carry the four",
"feedback": "This answer is wrong — you dropped the tetra- count from the second element — the prefix must carry the four."
},
{
"value": "tetraselenium monofluoride",
"misconception": "you crossed the prefixes over — SeF₄ has ONE Se and FOUR F, so tetra- must count the F atoms, not the Se",
"feedback": "This answer is wrong — you crossed the prefixes over — SeF₄ has ONE Se and FOUR F, so tetra- must count the F atoms, not the Se."
}
]
feedback
{
"keyExplanation": "One Se atom drops mono- (mono- is dropped only on the FIRST element, never the second), and the four F atoms take tetra- with the -ide ending: SeF₄ is selenium tetrafluoride.",
"anticipatedWrong": [
{
"value": "monoselenium tetrafluoride",
"misconception": "you added mono- to the first element — mono- is always dropped on the first element",
"feedback": "This answer is wrong — you added mono- to the first element — mono- is always dropped on the first element."
},
{
"value": "selenium fluoride",
"misconception": "you dropped the tetra- count from the second element — the prefix must carry the four",
"feedback": "This answer is wrong — you dropped the tetra- count from the second element — the prefix must carry the four."
},
{
"value": "tetraselenium monofluoride",
"misconception": "you crossed the prefixes over — SeF₄ has ONE Se and FOUR F, so tetra- must count the F atoms, not the Se",
"feedback": "This answer is wrong — you crossed the prefixes over — SeF₄ has ONE Se and FOUR F, so tetra- must count the F atoms, not the Se."
}
]
}
CMB-008 · medium · application · seq 14 · AUTHORED (tellurium tetrachloride TeCl4 per ledger; seed pool[21] frame) · text
Write the formula of tellurium tetrachloride.
Answer: TeCl₄ KEY
also accepted: TeCl4
wrongValueDiagnostics
[
{
"value": "Te₄Cl",
"misconception": "you attached the count to the wrong element — tetra- belongs to chloride, so the 4 follows Cl",
"feedback": "This answer is wrong — you attached the count to the wrong element — tetra- belongs to chloride, so the 4 follows Cl."
},
{
"value": "TeCl",
"misconception": "you dropped the count — tetra- means the formula needs a 4 after Cl",
"feedback": "This answer is wrong — you dropped the count — tetra- means the formula needs a 4 after Cl."
}
]
feedback
{
"keyExplanation": "Tellurium has no prefix — one Te, no subscript. tetra- means four, so Cl takes the subscript 4. Tellurium tetrachloride is TeCl₄.",
"anticipatedWrong": [
{
"value": "Te₄Cl",
"misconception": "you attached the count to the wrong element — tetra- belongs to chloride, so the 4 follows Cl",
"feedback": "This answer is wrong — you attached the count to the wrong element — tetra- belongs to chloride, so the 4 follows Cl."
},
{
"value": "TeCl",
"misconception": "you dropped the count — tetra- means the formula needs a 4 after Cl",
"feedback": "This answer is wrong — you dropped the count — tetra- means the formula needs a 4 after Cl."
}
]
}
CMB-019 · medium · application · seq 15 · seed:U5-G1/pool[56] (CMB-019 gateItems) — HCN (019 article instance) -> CBrF3 per ledger; appears-once tiebreak kept; 'None of the above' REPLACED · mcq4
Which atom is the central atom of CBrF₃?
Carbon KEY
Bromine
Fluorine
Whichever atom the formula names last.
CMB-018 · medium · application · seq 16 · AUTHORED to the seed pattern (anonymized X₂, Group 17 — recorded license; fresh diatomic space exhausted) · mcq4
The periodic table places element X in Group 17. Two X atoms pair into the molecule X₂. Which picture shows the correct Lewis diagram of X₂?
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "X₂",
"structure": "X–X joined by one line; three dot pairs on each X, drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "X₂ (wrong)",
"structure": "X–X joined by one line; only TWO dot pairs on each X (10 electrons drawn in total)",
"style": "clean Lewis diagram, deliberately short of lone pairs"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "X₂ (wrong)",
"structure": "two X symbols side by side with NO line; three dot pairs on one X, four dot pairs on the other (all 14 electrons as dots)",
"style": "clean Lewis diagram, deliberately missing the bond line"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "X₂ (wrong)",
"structure": "a circle labeled X⁺ and a separate circle labeled X⁻ with a curved arrow showing one electron moved between them — a transfer picture",
"style": "particulate transfer diagram, deliberately the wrong representation"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-020 · hard · transfer · seq 17 · AUTHORED to the seed pattern (PI3 per ledger) · mcq4
Which picture shows the correct Lewis diagram of PI₃? The periodic table places phosphorus in Group 15, with iodine in Group 17.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PI₃",
"structure": "P central, joined by one line to each of three I symbols; one dot pair on the P; three dot pairs on each I, drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PI₃ (wrong)",
"structure": "P central with three lines to I symbols; NO dots on the P; three dot pairs on each I (24 electrons drawn)",
"style": "clean Lewis diagram, deliberately missing the central lone pair"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PI₃ (wrong)",
"structure": "an I central, joined by one line to the P and one line to each of the other two I symbols; three dot pairs on the P and on each outer I; one dot pair on the central I (26 electrons drawn)",
"style": "clean Lewis diagram, deliberately wrong central atom"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PI₃ (wrong)",
"structure": "P central with three lines to I symbols; no dots on the P; three dot pairs on two of the iodines and FOUR dot pairs on the third",
"style": "clean Lewis diagram, deliberately misplacing the last lone pair"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-021 · hard · transfer · seq 18 · AUTHORED (who-lends facet, element-free) · mcq4
A Lewis diagram's central atom sits below eight after every electron is placed, so a conversion is needed. Which atom supplies the pair that becomes the new shared pair?
A neighboring atom that has a lone pair — never a hydrogen. KEY
The short central atom itself.
Any hydrogen bonded to the central atom.
An atom from outside the molecule.
CMB-009 · hard · transfer · seq 19 · AUTHORED (SrBr2 'strontium bromide' per ledger; seed pool[24] ionic frame) · text
Name SrBr₂.
Answer: strontium bromide KEY
also accepted: Strontium bromide
wrongValueDiagnostics
[
{
"value": "strontium dibromide",
"misconception": "you counted with prefixes — strontium is a metal, so SrBr₂ is ionic, and ionic names never use prefixes",
"feedback": "This answer is wrong — you counted with prefixes — strontium is a metal, so SrBr₂ is ionic, and ionic names never use prefixes."
},
{
"value": "strontium(II) bromide",
"misconception": "you added a Roman numeral — strontium forms only Sr²⁺, so no numeral is needed and none is written",
"feedback": "This answer is wrong — you added a Roman numeral — strontium forms only Sr²⁺, so no numeral is needed and none is written."
}
]
feedback
{
"keyExplanation": "First element: strontium, a metal — ionic naming, no prefixes. The two bromines come from the charges (two Br⁻ balance one Sr²⁺), so the name is simply strontium bromide.",
"anticipatedWrong": [
{
"value": "strontium dibromide",
"misconception": "you counted with prefixes — strontium is a metal, so SrBr₂ is ionic, and ionic names never use prefixes",
"feedback": "This answer is wrong — you counted with prefixes — strontium is a metal, so SrBr₂ is ionic, and ionic names never use prefixes."
},
{
"value": "strontium(II) bromide",
"misconception": "you added a Roman numeral — strontium forms only Sr²⁺, so no numeral is needed and none is written",
"feedback": "This answer is wrong — you added a Roman numeral — strontium forms only Sr²⁺, so no numeral is needed and none is written."
}
]
}
CMB-022 · hard · transfer · seq 20 · seed:U5-G1/pool[65] (CMB-022 gateItems) — N2 (022 article instance) -> CH3SH drawn correctly per ledger (no fresh diatomic-triple exists; correct-verdict case class kept; thiol scenery flagged) · mcq4
The figure shows a student's Lewis diagram of methanethiol, CH₃SH. Its supply comes to 14 electrons overall. Run the two checks. What is the verdict?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃SH" · structure: "C joined by single lines to three H symbols and to S; S joined by a single line to the fourth H; two radial lone pairs on the S; no other dots" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃SH",
"structure": "C joined by single lines to three H symbols and to S; S joined by a single line to the fourth H; two radial lone pairs on the S; no other dots",
"style": "clean textbook Lewis diagram"
}
}
The diagram is correct. KEY
The total number of electrons shown is too high.
The total number of electrons shown is too low.
The total is right, but an atom is short of its eight.
Use the five-step routine to plan the Lewis diagram of phosphorus trifluoride, PF₃. The periodic table places phosphorus in Group 15, with fluorine in Group 17. Set out your reasoning in the answer box:
FIGURE (model_answer_diagram · model_answer_diagram) — see raw specraw spec
{
"figureShape": "model_answer_diagram",
"modelAnswerFigureSpecs": {
"c": {
"figureType": "lewis-diagram",
"molecule": "PF₃",
"structure": "P central joined by single lines to three F symbols; one radial lone pair on the P; three radial lone pairs on each F",
"style": "clean textbook Lewis diagram"
}
}
}
Use the five-step routine to plan the Lewis diagram of phosphorus trifluoride, PF₃. The periodic table places phosphorus in Group 15, with fluorine in Group 17. Set out your reasoning in the answer box:
(a) State the total number of valence electrons, showing the count for each element.
(b) Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
(c) Describe the finished diagram — state where every lone pair sits, including any on the central atom — and show that both checks pass: the electrons drawn match the total, and every atom reaches eight.
Part a. State the total number of valence electrons, showing the count for each element.
Part b. Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
Model: Phosphorus is the central atom because it can form the most bonds — three, while fluorine forms one. The skeleton is the phosphorus in the middle joined by a single line to each of the three fluorines: three lines, using 6 of the 26 electrons.
Part c. Describe the finished diagram — state where every lone pair sits, including any on the central atom — and show that both checks pass: the electrons drawn match the total, and every atom reaches eight.
Model: The remaining 20 electrons sit as three lone pairs on each fluorine and ONE lone pair on the phosphorus, every pair pointing straight out with its dots side by side. Check 1: three lines (6) plus ten lone pairs (20) = 26 electrons drawn, matching the total. Check 2: the phosphorus counts three shared pairs plus its lone pair = 8; each fluorine counts one shared pair plus three lone pairs = 8. Both checks pass, so step 5 (conversion) is not needed.
Full model answer. (a) phosphorus: 1 atom × 5 valence electrons = 5; fluorine: 3 atoms × 7 = 21. Total = 5 + 21 = 26 valence electrons.
(b) Phosphorus is the central atom because it can form the most bonds — three, while fluorine forms one. The skeleton is the phosphorus in the middle joined by a single line to each of the three fluorines: three lines, using 6 of the 26 electrons.
(c) The remaining 20 electrons sit as three lone pairs on each fluorine and ONE lone pair on the phosphorus, every pair pointing straight out with its dots side by side. Check 1: three lines (6) plus ten lone pairs (20) = 26 electrons drawn, matching the total. Check 2: the phosphorus counts three shared pairs plus its lone pair = 8; each fluorine counts one shared pair plus three lone pairs = 8. Both checks pass, so step 5 (conversion) is not needed.
In a stable molecule, a shared pair of electrons sits between two bonded atoms. When you count each atom's surrounding electrons against the octet pattern, how does that shared pair count?
It counts for both atoms — each bonded atom includes every pair it shares. KEY
It counts only for the atom that originally contributed the two electrons.
It counts for neither atom, since neither one owns it outright.
It counts one electron for each atom — the pair is split down the middle.
Pentane has the molecular formula C₅H₁₂. How many atoms in total does one pentane molecule contain?
Answer: 17 atoms KEY
also accepted: 17 atoms, 17.0
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted the elements, not the atoms — add the two subscripts: 5 + 12",
"feedback": "This answer is wrong — you counted the elements, not the atoms — add the two subscripts: 5 + 12."
},
{
"value": 12,
"misconception": "you took the largest subscript as the total — every element's count joins the sum",
"feedback": "This answer is wrong — you took the largest subscript as the total — every element's count joins the sum."
},
{
"value": 5,
"misconception": "you read only the first subscript — the 12 hydrogens count too",
"feedback": "This answer is wrong — you read only the first subscript — the 12 hydrogens count too."
}
]
feedback
{
"keyExplanation": "Each subscript counts its own element: 5 carbon and 12 hydrogen. The total is 5 + 12 = 17 atoms in one pentane molecule.",
"anticipatedWrong": [
{
"value": 2,
"misconception": "you counted the elements, not the atoms — add the two subscripts: 5 + 12",
"feedback": "This answer is wrong — you counted the elements, not the atoms — add the two subscripts: 5 + 12."
},
{
"value": 12,
"misconception": "you took the largest subscript as the total — every element's count joins the sum",
"feedback": "This answer is wrong — you took the largest subscript as the total — every element's count joins the sum."
},
{
"value": 5,
"misconception": "you read only the first subscript — the 12 hydrogens count too",
"feedback": "This answer is wrong — you read only the first subscript — the 12 hydrogens count too."
}
]
}
CMB-001 · medium · application · seq 5 · AUTHORED to the seed pattern (panel order flipped); K->I / Te-H per ledger · mcq4
The figure's diagrams 1 and 2 each picture one bonded pair. Which classification is correct?
FIGURE (particulate-bond-panels · stimulus) — panels: [{"panel": "1", "description": "a larger circle labeled Te overlapping a smaller circle labeled H, with two dots in the overlap region"}, {"panel": "2", "des… · style: "clean textbook particulate diagrams, boxed panels"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "particulate-bond-panels",
"panels": [
{
"panel": "1",
"description": "a larger circle labeled Te overlapping a smaller circle labeled H, with two dots in the overlap region"
},
{
"panel": "2",
"description": "a circle labeled K⁺ and a separate circle labeled I⁻, with a curved arrow showing one electron moved from K to I"
}
],
"style": "clean textbook particulate diagrams, boxed panels"
}
}
Diagram 1 shows sharing, and diagram 2 shows transfer. KEY
Diagram 1 shows transfer, and diagram 2 shows sharing.
Two atoms, T and V, hold two shared pairs of electrons between them. One student argues that the bond cannot be covalent because no electron ever moved from one atom to the other. Which response is right?
The bond is covalent — sharing pairs is exactly what makes a bond covalent, and nothing needs to move. KEY
The student is right — every bond starts with an electron moving between atoms.
The bond is covalent only if the two pairs later move onto one atom.
Two shared pairs make the bond half covalent, because only one of the pairs really counts.
A student says two covalently bonded atoms stay together because 'their filled outer shells snap together like puzzle pieces.' What actually holds the atoms together?
Both positive nuclei attract the same negative shared electrons sitting between them. KEY
The student is right — filled shells physically interlock.
The two nuclei attract each other directly.
The shared electrons repel both nuclei equally, pinning the atoms in place.
CMB-011 · medium · application · seq 8 · AUTHORED (count facet on dimethyl ether CH3OCH3 per ledger; seed pool[31] pattern) · mcq4
How many lone pairs does the whole Lewis diagram of dimethyl ether, CH₃OCH₃, shown in the figure contain?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃OCH₃" · structure: "an O symbol in the middle joined by one line to each of two C symbols; each C joined by single lines to three H symbols; two dot pairs on the O drawn radial… · style: "clean Lewis diagram; lone pairs radial, dots equidistant"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃OCH₃",
"structure": "an O symbol in the middle joined by one line to each of two C symbols; each C joined by single lines to three H symbols; two dot pairs on the O drawn radially; no dots anywhere else",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
}
2 KEY
8
10
4
CMB-013 · medium · application · seq 9 · AUTHORED (two-doubles chain on 1,3-butadiene C4H6 per ledger; seed pool[37] pattern) · mcq4
The figure shows the Lewis diagram of 1,3-butadiene, C₄H₆, with the three bonds along the chain labeled 1, 2, and 3. Which statement classifies bonds 1, 2, and 3?
FIGURE (lewis-diagram · stimulus) — molecule: "C₄H₆" · structure: "a four-atom chain: two lines between the first and second chain atoms labeled 1, one line between the second and third labeled 2, two lines between the thir… · style: "clean Lewis diagram; bond labels as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₄H₆",
"structure": "a four-atom chain: two lines between the first and second chain atoms labeled 1, one line between the second and third labeled 2, two lines between the third and fourth labeled 3; H atoms joined by single lines so the chain atoms carry 2, 1, 1, and 2 hydrogens in order; no dots anywhere",
"style": "clean Lewis diagram; bond labels as small numbered arrows"
}
}
Bonds 1 and 3 are double bonds; bond 2 is a single bond. KEY
Bond 2 is a double bond; bonds 1 and 3 are single bonds.
The figure shows a student's unfinished Lewis diagram of H₂Se. How many electrons currently surround the selenium atom?
FIGURE (lewis-diagram · stimulus) — molecule: "H₂Se (unfinished)" · structure: "Se joined by one line to each of two H symbols; only ONE dot pair on the Se so far, drawn radially — the second lone pair has not been placed yet" · style: "clean textbook Lewis diagram, deliberately unfinished on the selenium"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "H₂Se (unfinished)",
"structure": "Se joined by one line to each of two H symbols; only ONE dot pair on the Se so far, drawn radially — the second lone pair has not been placed yet",
"style": "clean textbook Lewis diagram, deliberately unfinished on the selenium"
}
}
Answer: 6 electrons KEY
also accepted: 6 electrons, 6.0
wrongValueDiagnostics
[
{
"value": 8,
"misconception": "you answered from the octet pattern instead of counting — this diagram is unfinished, so count what is actually drawn",
"feedback": "This answer is wrong — you answered from the octet pattern instead of counting — this diagram is unfinished, so count what is actually drawn."
},
{
"value": 4,
"misconception": "you counted only the bonding electrons — the lone pair already placed also surrounds the selenium",
"feedback": "This answer is wrong — you counted only the bonding electrons — the lone pair already placed also surrounds the selenium."
},
{
"value": 2,
"misconception": "you counted only the lone pair — the two shared pairs also surround the selenium",
"feedback": "This answer is wrong — you counted only the lone pair — the two shared pairs also surround the selenium."
}
]
feedback
{
"keyExplanation": "Count what is drawn, not what the finished diagram would show. The two Se–H shared pairs give 4 electrons, and the one lone pair placed so far gives 2 more. 4 + 2 = 6 electrons currently surround the selenium.",
"anticipatedWrong": [
{
"value": 8,
"misconception": "you answered from the octet pattern instead of counting — this diagram is unfinished, so count what is actually drawn",
"feedback": "This answer is wrong — you answered from the octet pattern instead of counting — this diagram is unfinished, so count what is actually drawn."
},
{
"value": 4,
"misconception": "you counted only the bonding electrons — the lone pair already placed also surrounds the selenium",
"feedback": "This answer is wrong — you counted only the bonding electrons — the lone pair already placed also surrounds the selenium."
},
{
"value": 2,
"misconception": "you counted only the lone pair — the two shared pairs also surround the selenium",
"feedback": "This answer is wrong — you counted only the lone pair — the two shared pairs also surround the selenium."
}
]
}
CMB-016 · medium · application · seq 11 · AUTHORED (anonymous 6-valence bonds-to-chlorine case per blueprint rotation; partner-count frame of pool[46]) · numeric
An atom of element M has six valence electrons. In one molecule it bonds only to atoms of element R, and each R atom forms exactly one bond. If every atom reaches its typical bond count, how many R atoms does the M atom bond to?
Answer: 2 atoms KEY
also accepted: 2 atoms, 2.0
scaffold
[
"Write down the values in the question:",
"valence electrons of M = 6",
"Write down the relationship:",
"typical bonds = 8 − valence electrons",
"Substitute in the values, and calculate:",
"typical bonds = 8 − 6 = 2",
"Each R atom forms one bond, so two bonds means 2 R atoms."
]
wrongValueDiagnostics
[
{
"value": 6,
"misconception": "you used M's valence count as the number of partners — the partners equal the bonds, which is 8 − 6",
"feedback": "This answer is wrong — you used M's valence count as the number of partners — the partners equal the bonds, which is 8 − 6."
},
{
"value": 8,
"misconception": "you used the full octet count as the number of partners — eight is the electron target, not the bond count",
"feedback": "This answer is wrong — you used the full octet count as the number of partners — eight is the electron target, not the bond count."
},
{
"value": 1,
"misconception": "you assumed M, like R, forms just one bond — M needs two more electrons, so it forms two bonds",
"feedback": "This answer is wrong — you assumed M, like R, forms just one bond — M needs two more electrons, so it forms two bonds."
}
]
feedback
{
"keyExplanation": "M typically forms 8 − 6 = 2 bonds. Each R atom forms one bond, so each bond uses one R atom. Two bonds means two R atoms.",
"anticipatedWrong": [
{
"value": 6,
"misconception": "you used M's valence count as the number of partners — the partners equal the bonds, which is 8 − 6",
"feedback": "This answer is wrong — you used M's valence count as the number of partners — the partners equal the bonds, which is 8 − 6."
},
{
"value": 8,
"misconception": "you used the full octet count as the number of partners — eight is the electron target, not the bond count",
"feedback": "This answer is wrong — you used the full octet count as the number of partners — eight is the electron target, not the bond count."
},
{
"value": 1,
"misconception": "you assumed M, like R, forms just one bond — M needs two more electrons, so it forms two bonds",
"feedback": "This answer is wrong — you assumed M, like R, forms just one bond — M needs two more electrons, so it forms two bonds."
}
]
}
CMB-017 · medium · application · seq 12 · AUTHORED (C2F6 = 50 per ledger; seed pool[48/49] frame) · numeric
Carbon is found in Group 14; fluorine is found in Group 17. Give the total number of valence electrons in one C₂F₆ molecule.
Answer: 50 valence electrons KEY
also accepted: 50 valence electrons, 50 electrons, 50.0
scaffold
[
"Write down the values in the question:",
"carbon: 2 atoms × 4 valence electrons",
"fluorine: 6 atoms × 7 valence electrons",
"Write down the relationship:",
"total valence electrons = the sum over every element of (atoms × valence electrons)",
"Substitute in the values, and calculate:",
"total valence electrons = 8 + 42 = 50"
]
wrongValueDiagnostics
[
{
"value": 11,
"misconception": "you counted one atom of each element — the subscripts mean two carbons and six fluorines",
"feedback": "This answer is wrong — you counted one atom of each element — the subscripts mean two carbons and six fluorines."
},
{
"value": 130,
"misconception": "you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven",
"feedback": "This answer is wrong — you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven."
},
{
"value": 8,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
feedback
{
"keyExplanation": "carbon: 2 atoms × 4 valence electrons\nfluorine: 6 atoms × 7 valence electrons\ntotal valence electrons = (2 × 4) + (6 × 7) = 8 + 42 = 50",
"anticipatedWrong": [
{
"value": 11,
"misconception": "you counted one atom of each element — the subscripts mean two carbons and six fluorines",
"feedback": "This answer is wrong — you counted one atom of each element — the subscripts mean two carbons and six fluorines."
},
{
"value": 130,
"misconception": "you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven",
"feedback": "This answer is wrong — you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven."
},
{
"value": 8,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
}
CMB-007 · medium · application · seq 13 · AUTHORED (B2O3 per ledger -> N2O5 QC wave 2 -> I2O5 packaging sweep: N2O5 is student-seen in CMB-005 fluency AND verbatim-recreated consumed seed pool[18] (= A#13's freshened seed); I2O5 has zero unit presence; penta+oxide elision facet kept) · text
Name the binary molecular compound I₂O₅.
Answer: diiodine pentoxide KEY
also accepted: Diiodine pentoxide, diiodine pentaoxide
wrongValueDiagnostics
[
{
"value": "iodine pentoxide",
"misconception": "you dropped di- from the first element — only mono- is ever dropped",
"feedback": "This answer is wrong — you dropped di- from the first element — only mono- is ever dropped."
},
{
"value": "diiodine oxide",
"misconception": "you dropped the penta- count from the second element — the prefix must carry the five",
"feedback": "This answer is wrong — you dropped the penta- count from the second element — the prefix must carry the five."
},
{
"value": "pentaiodine dioxide",
"misconception": "you swapped the two prefixes — each prefix belongs to the element it sits in front of",
"feedback": "This answer is wrong — you swapped the two prefixes — each prefix belongs to the element it sits in front of."
}
]
feedback
{
"keyExplanation": "Two I atoms take di- (di- is never dropped — only mono- is), and five O atoms take penta-: penta- + oxide becomes pentoxide. I₂O₅ is diiodine pentoxide.",
"anticipatedWrong": [
{
"value": "iodine pentoxide",
"misconception": "you dropped di- from the first element — only mono- is ever dropped",
"feedback": "This answer is wrong — you dropped di- from the first element — only mono- is ever dropped."
},
{
"value": "diiodine oxide",
"misconception": "you dropped the penta- count from the second element — the prefix must carry the five",
"feedback": "This answer is wrong — you dropped the penta- count from the second element — the prefix must carry the five."
},
{
"value": "pentaiodine dioxide",
"misconception": "you swapped the two prefixes — each prefix belongs to the element it sits in front of",
"feedback": "This answer is wrong — you swapped the two prefixes — each prefix belongs to the element it sits in front of."
}
]
}
CMB-008 · medium · application · seq 14 · AUTHORED (tetraphosphorus decasulfide P4S10 per ledger — carries the seed family's deca- decode) · text
Write the formula of tetraphosphorus decasulfide.
Answer: P₄S₁₀ KEY
also accepted: P4S10
wrongValueDiagnostics
[
{
"value": "P₁₀S₄",
"misconception": "you swapped the two counts — tetra- belongs to phosphorus and deca- to sulfide",
"feedback": "This answer is wrong — you swapped the two counts — tetra- belongs to phosphorus and deca- to sulfide."
},
{
"value": "PS₁₀",
"misconception": "you dropped tetra- — four phosphorus atoms need the subscript 4",
"feedback": "This answer is wrong — you dropped tetra- — four phosphorus atoms need the subscript 4."
}
]
feedback
{
"keyExplanation": "tetra- means four, so P takes the subscript 4; deca- means ten, so S takes the subscript 10. Tetraphosphorus decasulfide is P₄S₁₀.",
"anticipatedWrong": [
{
"value": "P₁₀S₄",
"misconception": "you swapped the two counts — tetra- belongs to phosphorus and deca- to sulfide",
"feedback": "This answer is wrong — you swapped the two counts — tetra- belongs to phosphorus and deca- to sulfide."
},
{
"value": "PS₁₀",
"misconception": "you dropped tetra- — four phosphorus atoms need the subscript 4",
"feedback": "This answer is wrong — you dropped tetra- — four phosphorus atoms need the subscript 4."
}
]
}
CMB-019 · medium · application · seq 15 · AUTHORED (bromoform CHBr3 per ledger; seed pool[54] frame) · mcq4
Which atom is the central atom of bromoform, CHBr₃?
Carbon KEY
Bromine
Hydrogen
The molecule has two central atoms — the carbon and the hydrogen share the middle.
CMB-018 · medium · application · seq 16 · AUTHORED to the seed pattern (anonymized H–X, Group 17 — recorded license) · mcq4
Element X is found in Group 17. One H atom bonds to one X atom in the two-atom molecule HX. Which picture shows the correct Lewis diagram of HX?
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "HX",
"structure": "H–X joined by one line; three dot pairs on the X, drawn radially; no dots on the H",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "HX (wrong)",
"structure": "H–X joined by one line; two dot pairs on the X and one dot pair on the H",
"style": "clean Lewis diagram, deliberately misplacing a lone pair on hydrogen"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "HX (wrong)",
"structure": "H–X joined by one line; only TWO dot pairs on the X (6 electrons drawn in total)",
"style": "clean Lewis diagram, deliberately short of lone pairs"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "HX (wrong)",
"structure": "H and X symbols side by side with NO line; one dot on the H and seven dots on the X grouped in pairs plus a single",
"style": "clean Lewis diagram, deliberately missing the bond line"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-020 · hard · transfer · seq 17 · AUTHORED to the seed pattern (SBr2 per ledger) · mcq4
Which picture shows the correct Lewis diagram of SBr₂? Sulfur is found in Group 16; bromine is found in Group 17.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SBr₂",
"structure": "S central, joined by one line to each of two Br symbols; two dot pairs on the S; three dot pairs on each Br, drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SBr₂ (wrong)",
"structure": "S central with two lines to Br symbols; only ONE dot pair on the S; three dot pairs on each Br (18 electrons drawn)",
"style": "clean Lewis diagram, deliberately short on the central atom"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SBr₂ (wrong)",
"structure": "a Br central, joined by one line to the S and one line to the other Br; three dot pairs on the S; three dot pairs on the outer Br; two dot pairs on the central Br (20 electrons drawn)",
"style": "clean Lewis diagram, deliberately wrong central atom"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SBr₂ (wrong)",
"structure": "S central with two lines to Br symbols; THREE dot pairs on the S and three dot pairs on each Br (22 electrons drawn)",
"style": "clean Lewis diagram, deliberately one lone pair over the total"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-021 · hard · transfer · seq 18 · AUTHORED (when-to-stop facet, element-free) · mcq4
A student has just converted one lone pair into a second shared pair. How does the student decide whether to stop or convert another pair?
Stop once every atom counts eight, with hydrogen at two. KEY
Stop after one conversion — a second one would crowd the central atom past eight.
Keep converting until no lone pairs remain anywhere in the diagram.
Stop when the diagram's total electron count reaches eight.
CMB-009 · hard · transfer · seq 19 · AUTHORED (SeF6 'selenium hexafluoride' per ledger; seed pool[25] molecular frame) · text
Name SeF₆.
Answer: selenium hexafluoride KEY
also accepted: Selenium hexafluoride
wrongValueDiagnostics
[
{
"value": "selenium fluoride",
"misconception": "you skipped the count — selenium and fluorine are both nonmetals, so prefixes are required: six fluorines need hexa-",
"feedback": "This answer is wrong — you skipped the count — selenium and fluorine are both nonmetals, so prefixes are required: six fluorines need hexa-."
},
{
"value": "selenium(VI) fluoride",
"misconception": "you used a Roman numeral — numerals mark metals with more than one common ion charge; molecular compounds count with prefixes",
"feedback": "This answer is wrong — you used a Roman numeral — numerals mark metals with more than one common ion charge; molecular compounds count with prefixes."
}
]
feedback
{
"keyExplanation": "Both elements are nonmetals, so SeF₆ is molecular and takes prefix naming: one selenium (mono- dropped), six fluorines — selenium hexafluoride.",
"anticipatedWrong": [
{
"value": "selenium fluoride",
"misconception": "you skipped the count — selenium and fluorine are both nonmetals, so prefixes are required: six fluorines need hexa-",
"feedback": "This answer is wrong — you skipped the count — selenium and fluorine are both nonmetals, so prefixes are required: six fluorines need hexa-."
},
{
"value": "selenium(VI) fluoride",
"misconception": "you used a Roman numeral — numerals mark metals with more than one common ion charge; molecular compounds count with prefixes",
"feedback": "This answer is wrong — you used a Roman numeral — numerals mark metals with more than one common ion charge; molecular compounds count with prefixes."
}
]
}
CMB-022 · hard · transfer · seq 20 · AUTHORED (too-many verdict on GeBr4 per ledger; seed pool[63/65] verdict frame) · mcq4
The figure shows a student's Lewis diagram of GeBr₄, which offers 32 electrons to place. Run the two checks. What is the verdict?
FIGURE (lewis-diagram · stimulus) — molecule: "GeBr₄ (a student's wrong diagram)" · structure: "Ge central with single lines to four Br symbols; three radial lone pairs on three of the bromines; FOUR radial lone pairs on the fourth bromine; no dots on … · style: "clean textbook Lewis diagram, deliberately wrong"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "GeBr₄ (a student's wrong diagram)",
"structure": "Ge central with single lines to four Br symbols; three radial lone pairs on three of the bromines; FOUR radial lone pairs on the fourth bromine; no dots on the Ge",
"style": "clean textbook Lewis diagram, deliberately wrong"
}
}
The diagram shows too many electrons. KEY
The diagram is correct.
The diagram shows too few electrons.
The total is right, but an atom is short of its eight.
Use the five-step routine to plan the Lewis diagram of ethanol, C₂H₅OH — its backbone is a two-carbon chain; the oxygen bonds to the second carbon, and the final hydrogen bonds to that oxygen. Oxygen is found in Group 16; carbon is found in Group 14; every hydrogen contributes one valence electron. Lay out your work in the answer box:
FIGURE (model_answer_diagram · model_answer_diagram) — see raw specraw spec
{
"figureShape": "model_answer_diagram",
"modelAnswerFigureSpecs": {
"c": {
"figureType": "lewis-diagram",
"molecule": "C₂H₅OH",
"structure": "C–C–O–H chain with single lines; three H on the first C and two H on the second C, all by single lines; two radial lone pairs on the O; no other dots",
"style": "clean textbook Lewis diagram"
}
}
}
Use the five-step routine to plan the Lewis diagram of ethanol, C₂H₅OH — its backbone is a two-carbon chain; the oxygen bonds to the second carbon, and the final hydrogen bonds to that oxygen. Oxygen is found in Group 16; carbon is found in Group 14; every hydrogen contributes one valence electron. Lay out your work in the answer box:
(a) State the total number of valence electrons, showing the count for each element.
(b) Describe the skeleton after the single lines are drawn, using the backbone given above.
(c) Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and every atom lands on eight while every hydrogen lands on two.
Part a. State the total number of valence electrons, showing the count for each element.
Part b. Describe the skeleton after the single lines are drawn, using the backbone given above.
Model: Using the given backbone, the first carbon joins the second carbon, and the second carbon joins the oxygen, which joins the last hydrogen. Three hydrogens sit on the first carbon and two on the second. That is eight single lines in all, using 16 of the 20 electrons.
Part c. Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and every atom lands on eight while every hydrogen lands on two.
Model: The remaining 4 electrons sit as two lone pairs on the oxygen, pointing straight out with the dots side by side; no other atom carries dots. Check 1: eight lines (16) plus two lone pairs (4) = 20 electrons drawn, matching the total. Check 2: each carbon counts four shared pairs = 8; the oxygen counts two shared pairs plus two lone pairs = 8; every hydrogen counts its one shared pair = 2. Both checks pass, so step 5 (conversion) is not needed.
Full model answer. (a) carbon: 2 atoms × 4 valence electrons = 8; hydrogen: 6 atoms × 1 = 6; oxygen: 1 atom × 6 = 6. Total = 8 + 6 + 6 = 20 valence electrons.
(b) Using the given backbone, the first carbon joins the second carbon, and the second carbon joins the oxygen, which joins the last hydrogen. Three hydrogens sit on the first carbon and two on the second. That is eight single lines in all, using 16 of the 20 electrons.
(c) The remaining 4 electrons sit as two lone pairs on the oxygen, pointing straight out with the dots side by side; no other atom carries dots. Check 1: eight lines (16) plus two lone pairs (4) = 20 electrons drawn, matching the total. Check 2: each carbon counts four shared pairs = 8; the oxygen counts two shared pairs plus two lone pairs = 8; every hydrogen counts its one shared pair = 2. Both checks pass, so step 5 (conversion) is not needed.
A student writes: 'In every stable molecule, every atom is surrounded by exactly eight electrons.' Which correction makes the statement match the octet pattern?
Change it to MOST stable molecules, and note that hydrogen's full count is two. KEY
No correction is needed — the statement is already the octet pattern.
Change eight to two for every atom in the molecule.
Restrict the statement to molecules built from a single element.
CMB-005 · easy · application · seq 4 · AUTHORED (total-atom facet; PBr5 per stage-2 patched ledger — the diborane draft kept 'hydrogen', an own-lesson 005 material; formula-reading only, no Lewis claim on the five-bond phosphorus) · numeric
How many atoms in total does one molecule of PBr₅ contain?
Answer: 6 atoms KEY
also accepted: 6 atoms, 6.0
wrongValueDiagnostics
[
{
"value": 5,
"misconception": "you read only the bromine subscript — the phosphorus with no subscript still counts as one atom",
"feedback": "This answer is wrong — you read only the bromine subscript — the phosphorus with no subscript still counts as one atom."
},
{
"value": 2,
"misconception": "you counted the elements, not the atoms — add the counts: 1 + 5",
"feedback": "This answer is wrong — you counted the elements, not the atoms — add the counts: 1 + 5."
}
]
feedback
{
"keyExplanation": "The P with no subscript counts as one atom, and the subscript after Br counts five more. The total is 1 + 5 = 6 atoms in one PBr₅ molecule.",
"anticipatedWrong": [
{
"value": 5,
"misconception": "you read only the bromine subscript — the phosphorus with no subscript still counts as one atom",
"feedback": "This answer is wrong — you read only the bromine subscript — the phosphorus with no subscript still counts as one atom."
},
{
"value": 2,
"misconception": "you counted the elements, not the atoms — add the counts: 1 + 5",
"feedback": "This answer is wrong — you counted the elements, not the atoms — add the counts: 1 + 5."
}
]
}
CMB-001 · medium · application · seq 5 · AUTHORED to the seed pattern; Li->I / Se-Cl per ledger · mcq4
In the figure, diagrams 1 and 2 each show one bonding arrangement. Which classification is correct?
FIGURE (particulate-bond-panels · stimulus) — panels: [{"panel": "1", "description": "a circle labeled Li⁺ and a separate circle labeled I⁻, with a curved arrow showing one electron moved from Li to I"}, {"panel… · style: "clean textbook particulate diagrams, boxed panels"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "particulate-bond-panels",
"panels": [
{
"panel": "1",
"description": "a circle labeled Li⁺ and a separate circle labeled I⁻, with a curved arrow showing one electron moved from Li to I"
},
{
"panel": "2",
"description": "a larger circle labeled Se overlapping a smaller circle labeled Cl, with two dots in the overlap region"
}
],
"style": "clean textbook particulate diagrams, boxed panels"
}
}
Diagram 1 shows transfer, and diagram 2 shows sharing. KEY
Diagram 1 shows sharing, and diagram 2 shows transfer.
In one bond, an electron has moved completely from one atom onto its partner, and the two charged atoms now sit side by side. A student calls the bond covalent 'because the atoms ended up together.' Which correction is right?
The bond is not covalent — a covalent bond needs one or more SHARED pairs, and a moved electron is not shared. KEY
The student is right — any two atoms that stay together are covalently bonded.
The bond is covalent because the moved electron still belongs a little to its old atom.
The bond is covalent because exactly one electron was involved.
In a covalent bond the shared electrons sit between the two nuclei. Why does that position let the bond hold the atoms together?
From between, the negative pair pulls each positive nucleus toward itself — and so toward the other atom. KEY
From between, the pair keeps the two nuclei from repelling each other.
The between-position lets each nucleus reclaim its own electron whenever the bond stretches.
The electrons take up space between the atoms and physically block them from drifting apart.
CMB-011 · medium · application · seq 8 · AUTHORED (count facet on hydrogen disulfide H2S2 per ledger — H2O2 chain topology; obscure-but-real flagged, figure carries the structure) · mcq4
How many lone pairs does the whole Lewis diagram of hydrogen disulfide, H₂S₂, shown in the figure contain?
FIGURE (lewis-diagram · stimulus) — molecule: "H₂S₂" · structure: "H–S–S–H chain joined by single lines; two dot pairs on each S drawn radially; no dots on the H symbols" · style: "clean Lewis diagram; lone pairs radial, dots equidistant"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "H₂S₂",
"structure": "H–S–S–H chain joined by single lines; two dot pairs on each S drawn radially; no dots on the H symbols",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
}
4 KEY
7
2
8
CMB-013 · medium · application · seq 9 · AUTHORED (double-bond read on tetrafluoroethene C2F4 per ledger; seed pool[38] pattern) · mcq4
The figure shows the Lewis diagram of tetrafluoroethene, C₂F₄, with the bond between the two middle atoms labeled 1. Classify bond 1.
FIGURE (lewis-diagram · stimulus) — molecule: "C₂F₄" · structure: "two middle symbols joined by two parallel lines labeled 1; each also joined by single lines to two F symbols; three dot pairs on each F drawn radially; no d… · style: "clean Lewis diagram; lone pairs radial, dots equidistant; bond labels as small numbered arrows"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₂F₄",
"structure": "two middle symbols joined by two parallel lines labeled 1; each also joined by single lines to two F symbols; three dot pairs on each F drawn radially; no dots on the middle atoms",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant; bond labels as small numbered arrows"
}
}
A double bond. KEY
A single bond.
A six-fold bond — the two lines at bond 1 plus the four outer lines.
A triple bond.
CMB-015 · medium · application · seq 10 · AUTHORED (bonds-plus-lone-pair facet on PBr3 per ledger; freshness_scope_article WARN recorded — PBr3 appears in CMB-009's article) · numeric
The figure shows the Lewis diagram of PBr₃. How many electrons surround the phosphorus atom?
FIGURE (lewis-diagram · stimulus) — molecule: "PBr₃" · structure: "P central, joined by one line to each of three Br symbols; one dot pair on the P; three dot pairs on each Br; all lone pairs radial" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PBr₃",
"structure": "P central, joined by one line to each of three Br symbols; one dot pair on the P; three dot pairs on each Br; all lone pairs radial",
"style": "clean textbook Lewis diagram"
}
}
Answer: 8 electrons KEY
also accepted: 8 electrons, 8.0
wrongValueDiagnostics
[
{
"value": 6,
"misconception": "you skipped the phosphorus's own lone pair — its two electrons surround the phosphorus too",
"feedback": "This answer is wrong — you skipped the phosphorus's own lone pair — its two electrons surround the phosphorus too."
},
{
"value": 4,
"misconception": "you counted the pairs, not the electrons — four pairs touch the phosphorus, each holding two electrons",
"feedback": "This answer is wrong — you counted the pairs, not the electrons — four pairs touch the phosphorus, each holding two electrons."
},
{
"value": 26,
"misconception": "you counted every electron in the diagram — the bromines' lone pairs belong to the bromines",
"feedback": "This answer is wrong — you counted every electron in the diagram — the bromines' lone pairs belong to the bromines."
}
]
feedback
{
"keyExplanation": "Three shared pairs touch the phosphorus (6 electrons), and its own lone pair adds 2 more. 6 + 2 = 8 electrons surround the phosphorus.",
"anticipatedWrong": [
{
"value": 6,
"misconception": "you skipped the phosphorus's own lone pair — its two electrons surround the phosphorus too",
"feedback": "This answer is wrong — you skipped the phosphorus's own lone pair — its two electrons surround the phosphorus too."
},
{
"value": 4,
"misconception": "you counted the pairs, not the electrons — four pairs touch the phosphorus, each holding two electrons",
"feedback": "This answer is wrong — you counted the pairs, not the electrons — four pairs touch the phosphorus, each holding two electrons."
},
{
"value": 26,
"misconception": "you counted every electron in the diagram — the bromines' lone pairs belong to the bromines",
"feedback": "This answer is wrong — you counted every electron in the diagram — the bromines' lone pairs belong to the bromines."
}
]
}
CMB-016 · medium · application · seq 11 · AUTHORED (germanium Group-14 case per ledger; seed pool[45] group-position frame) · numeric
Germanium is in Group 14, so a germanium atom has four valence electrons. How many covalent bonds does germanium typically form?
Answer: 4 bonds KEY
also accepted: 4 bonds, 4.0
scaffold
[
"Write down the values in the question:",
"valence electrons = 4",
"Write down the relationship:",
"typical bonds = 8 − valence electrons",
"Substitute in the values, and calculate:",
"typical bonds = 8 − 4",
"typical bonds = 4"
]
wrongValueDiagnostics
[
{
"value": 14,
"misconception": "you used the group number as the bond count — Group 14 atoms have four valence electrons and need four more",
"feedback": "This answer is wrong — you used the group number as the bond count — Group 14 atoms have four valence electrons and need four more."
},
{
"value": 8,
"misconception": "you answered with the octet target — eight is the electron goal, not the number of bonds",
"feedback": "This answer is wrong — you answered with the octet target — eight is the electron goal, not the number of bonds."
}
]
feedback
{
"keyExplanation": "Write down the values in the question:\nvalence electrons = 4\nWrite down the relationship:\ntypical bonds = 8 − valence electrons\nSubstitute in the values, and calculate:\ntypical bonds = 8 − 4\ntypical bonds = 4",
"anticipatedWrong": [
{
"value": 14,
"misconception": "you used the group number as the bond count — Group 14 atoms have four valence electrons and need four more",
"feedback": "This answer is wrong — you used the group number as the bond count — Group 14 atoms have four valence electrons and need four more."
},
{
"value": 8,
"misconception": "you answered with the octet target — eight is the electron goal, not the number of bonds",
"feedback": "This answer is wrong — you answered with the octet target — eight is the electron goal, not the number of bonds."
}
]
}
CMB-017 · medium · application · seq 12 · AUTHORED (C2Cl4 = 36 per ledger; seed pool[48/49] frame) · numeric
Carbon (Group 14) and chlorine (Group 17) build the molecule C₂Cl₄. How many valence electrons does one C₂Cl₄ molecule hold in total?
Answer: 36 valence electrons KEY
also accepted: 36 valence electrons, 36 electrons, 36.0
scaffold
[
"Write down the values in the question:",
"carbon: 2 atoms × 4 valence electrons",
"chlorine: 4 atoms × 7 valence electrons",
"Write down the relationship:",
"total valence electrons = the sum over every element of (atoms × valence electrons)",
"Substitute in the values, and calculate:",
"total valence electrons = 8 + 28 = 36"
]
wrongValueDiagnostics
[
{
"value": 11,
"misconception": "you counted one atom of each element — the subscripts mean two carbons and four chlorines",
"feedback": "This answer is wrong — you counted one atom of each element — the subscripts mean two carbons and four chlorines."
},
{
"value": 96,
"misconception": "you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven",
"feedback": "This answer is wrong — you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven."
},
{
"value": 6,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
feedback
{
"keyExplanation": "carbon: 2 atoms × 4 valence electrons\nchlorine: 4 atoms × 7 valence electrons\ntotal valence electrons = (2 × 4) + (4 × 7) = 8 + 28 = 36",
"anticipatedWrong": [
{
"value": 11,
"misconception": "you counted one atom of each element — the subscripts mean two carbons and four chlorines",
"feedback": "This answer is wrong — you counted one atom of each element — the subscripts mean two carbons and four chlorines."
},
{
"value": 96,
"misconception": "you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven",
"feedback": "This answer is wrong — you used the group numbers 14 and 17 as valence counts — the valence counts are four and seven."
},
{
"value": 6,
"misconception": "you counted the atoms in the formula, not their valence electrons",
"feedback": "This answer is wrong — you counted the atoms in the formula, not their valence electrons."
}
]
}
CMB-007 · medium · application · seq 13 · AUTHORED (N2F4 'dinitrogen tetrafluoride' per ledger) · text
Name the binary molecular compound N₂F₄.
Answer: dinitrogen tetrafluoride KEY
also accepted: Dinitrogen tetrafluoride
wrongValueDiagnostics
[
{
"value": "nitrogen tetrafluoride",
"misconception": "you dropped di- from the first element — only mono- is ever dropped; two nitrogens need di-",
"feedback": "This answer is wrong — you dropped di- from the first element — only mono- is ever dropped; two nitrogens need di-."
},
{
"value": "dinitrogen fluoride",
"misconception": "you left the four fluorines uncounted — the second element needs tetra-",
"feedback": "This answer is wrong — you left the four fluorines uncounted — the second element needs tetra-."
}
]
feedback
{
"keyExplanation": "Two nitrogens keep di-, four fluorines take tetra- with the -ide ending: fluorine becomes fluoride. N₂F₄ is dinitrogen tetrafluoride.",
"anticipatedWrong": [
{
"value": "nitrogen tetrafluoride",
"misconception": "you dropped di- from the first element — only mono- is ever dropped; two nitrogens need di-",
"feedback": "This answer is wrong — you dropped di- from the first element — only mono- is ever dropped; two nitrogens need di-."
},
{
"value": "dinitrogen fluoride",
"misconception": "you left the four fluorines uncounted — the second element needs tetra-",
"feedback": "This answer is wrong — you left the four fluorines uncounted — the second element needs tetra-."
}
]
}
CMB-008 · medium · application · seq 14 · AUTHORED (silicon tetraiodide SiI4 per ledger) · text
Write the formula of silicon tetraiodide.
Answer: SiI₄ KEY
also accepted: SiI4
wrongValueDiagnostics
[
{
"value": "Si₄I",
"misconception": "you attached the count to the wrong element — tetra- belongs to iodide, so the 4 follows I",
"feedback": "This answer is wrong — you attached the count to the wrong element — tetra- belongs to iodide, so the 4 follows I."
},
{
"value": "SiI",
"misconception": "you dropped the count — tetra- means the formula needs a 4 after I",
"feedback": "This answer is wrong — you dropped the count — tetra- means the formula needs a 4 after I."
}
]
feedback
{
"keyExplanation": "Silicon has no prefix — one Si, no subscript. tetra- means four, so I takes the subscript 4. Silicon tetraiodide is SiI₄.",
"anticipatedWrong": [
{
"value": "Si₄I",
"misconception": "you attached the count to the wrong element — tetra- belongs to iodide, so the 4 follows I",
"feedback": "This answer is wrong — you attached the count to the wrong element — tetra- belongs to iodide, so the 4 follows I."
},
{
"value": "SiI",
"misconception": "you dropped the count — tetra- means the formula needs a 4 after I",
"feedback": "This answer is wrong — you dropped the count — tetra- means the formula needs a 4 after I."
}
]
}
CMB-019 · medium · application · seq 15 · AUTHORED (CH2FCl per ledger; every outer atom placed by bond count) · mcq4
Which atom is the central atom of CH₂FCl?
Carbon KEY
Fluorine
Chlorine
Hydrogen
CMB-018 · medium · application · seq 16 · AUTHORED to the seed pattern (anonymized X–Y, two different Group 17 elements — recorded license) · mcq4
X and Y stand for two different elements, both Group 17 members. Which picture shows the correct Lewis diagram of the two-atom molecule XY?
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "XY",
"structure": "X–Y joined by one line; three dot pairs on the X and three dot pairs on the Y, drawn radially",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "XY (wrong)",
"structure": "a circle labeled X⁺ and a separate circle labeled Y⁻ with a curved arrow showing one electron moved from X to Y — a transfer picture",
"style": "particulate transfer diagram, deliberately the wrong representation"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "XY (wrong)",
"structure": "X–Y joined by one line; only TWO dot pairs on each atom (10 electrons drawn in total)",
"style": "clean Lewis diagram, deliberately short of lone pairs"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "XY (wrong)",
"structure": "X–Y joined by one line; six dot pairs all on the Y and none on the X",
"style": "clean Lewis diagram, deliberately piling the lone pairs on one atom"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-020 · hard · transfer · seq 17 · AUTHORED to the seed pattern (CH2Br2 per ledger) · mcq4
Which picture shows the correct Lewis diagram of CH₂Br₂? Use these facts: carbon (Group 14), bromine (Group 17), and hydrogen with one valence electron per atom.
FIGURE (figure · ) — see raw specraw spec
{
"option_format": "image",
"render_contract": "R2 image-XOR-text: options render as pictures ONLY; the 'Picture N' strings are internal ids for validation, never rendered and never used for aria (R23).",
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₂Br₂",
"structure": "C central, joined by single lines to two H symbols and two Br symbols; three dot pairs on each Br, drawn radially; no dots on C or H",
"style": "clean Lewis diagram; lone pairs radial, dots equidistant"
}
},
{
"option": "distractor1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₂Br₂ (wrong)",
"structure": "C central with lines to two H and two Br; one dot pair on each H; two dot pairs on each Br",
"style": "clean Lewis diagram, deliberately putting dots on hydrogens"
}
},
{
"option": "distractor2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₂Br₂ (wrong)",
"structure": "a Br central, joined by lines to the C, the other Br, and the two H symbols; dot pairs spread over the outer atoms",
"style": "clean Lewis diagram, deliberately wrong central atom"
}
},
{
"option": "distractor3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₂Br₂ (wrong)",
"structure": "C central with lines to two H and two Br; only TWO dot pairs on each Br (16 electrons drawn)",
"style": "clean Lewis diagram, deliberately short of the total"
}
}
]
}
Picture 1 KEY
Picture 2
Picture 3
Picture 4
CMB-021 · hard · transfer · seq 18 · AUTHORED (two-conversions facet, element-free) · mcq4
Every electron of a Lewis diagram is placed as single bonds and lone pairs, and the central atom sits at only four electrons. What does the routine call for?
Two conversions, each turning a neighbor's lone pair into a shared pair. KEY
One conversion, then two extra electrons added to finish.
Moving two lone pairs onto the central atom as lone pairs.
Accepting the diagram — some central atoms simply stay at four.
CMB-009 · hard · transfer · seq 19 · AUTHORED (Li2S 'lithium sulfide' per ledger; seed pool[24] ionic frame) · text
Name Li₂S.
Answer: lithium sulfide KEY
also accepted: lithium sulphide, Lithium sulfide
wrongValueDiagnostics
[
{
"value": "dilithium sulfide",
"misconception": "you counted with prefixes — lithium is a metal, so Li₂S is ionic, and ionic names never use prefixes",
"feedback": "This answer is wrong — you counted with prefixes — lithium is a metal, so Li₂S is ionic, and ionic names never use prefixes."
},
{
"value": "lithium(I) sulfide",
"misconception": "you added a Roman numeral — lithium forms only Li⁺, so no numeral is needed and none is written",
"feedback": "This answer is wrong — you added a Roman numeral — lithium forms only Li⁺, so no numeral is needed and none is written."
}
]
feedback
{
"keyExplanation": "First element: lithium, a metal — ionic naming, no prefixes. The two lithiums come from the charges (two Li⁺ balance one S²⁻), so the name is simply lithium sulfide.",
"anticipatedWrong": [
{
"value": "dilithium sulfide",
"misconception": "you counted with prefixes — lithium is a metal, so Li₂S is ionic, and ionic names never use prefixes",
"feedback": "This answer is wrong — you counted with prefixes — lithium is a metal, so Li₂S is ionic, and ionic names never use prefixes."
},
{
"value": "lithium(I) sulfide",
"misconception": "you added a Roman numeral — lithium forms only Li⁺, so no numeral is needed and none is written",
"feedback": "This answer is wrong — you added a Roman numeral — lithium forms only Li⁺, so no numeral is needed and none is written."
}
]
}
CMB-022 · hard · transfer · seq 20 · AUTHORED (too-few verdict on SnCl4 per ledger; seed pool[63/65] verdict frame) · mcq4
The figure shows a student's Lewis diagram of CBr₄. Its available electron count is 32. Run the two checks. What is the verdict?
FIGURE (lewis-diagram · stimulus) — molecule: "CBr₄ (a student's wrong diagram)" · structure: "C central with single lines to four Br symbols; three radial lone pairs on three of the bromines; only TWO radial lone pairs on the fourth bromine; no dots … · style: "clean textbook Lewis diagram, deliberately wrong"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CBr₄ (a student's wrong diagram)",
"structure": "C central with single lines to four Br symbols; three radial lone pairs on three of the bromines; only TWO radial lone pairs on the fourth bromine; no dots on the C",
"style": "clean textbook Lewis diagram, deliberately wrong"
}
}
The diagram shows too few electrons. KEY
The diagram is correct.
The diagram shows too many electrons.
The total is right, but an atom is short of its eight.
CMB-023 · medium · application · seq 21 · AUTHORED (CH3F per ledger; prod-seed routine voice) · frq
Use the five-step routine to plan the Lewis diagram of fluoromethane, CH₃F. Use these facts: carbon (Group 14), fluorine (Group 17), and hydrogen with one valence electron per atom. Give your full plan in the answer box:
FIGURE (model_answer_diagram · model_answer_diagram) — see raw specraw spec
{
"figureShape": "model_answer_diagram",
"modelAnswerFigureSpecs": {
"c": {
"figureType": "lewis-diagram",
"molecule": "CH₃F",
"structure": "C central joined by single lines to three H symbols and one F symbol; three radial lone pairs on the F; no dots on C or H",
"style": "clean textbook Lewis diagram"
}
}
}
Use the five-step routine to plan the Lewis diagram of fluoromethane, CH₃F. Use these facts: carbon (Group 14), fluorine (Group 17), and hydrogen with one valence electron per atom. Give your full plan in the answer box:
(a) State the total number of valence electrons, showing the count for each element.
(b) Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
(c) Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and each atom finishes at eight and each hydrogen finishes at two.
Part a. State the total number of valence electrons, showing the count for each element.
Part b. Name the central atom, justify your choice from typical bond counts, and describe the skeleton after the single lines are drawn.
Model: Carbon is the central atom because it can form the most bonds — four, while hydrogen and fluorine each form one. The skeleton is the carbon in the middle joined by single lines to the three hydrogens and the fluorine: four lines, using 8 of the 14 electrons.
Part c. Describe the finished diagram — state where every lone pair sits — and show that both checks pass: the electrons drawn match the total, and each atom finishes at eight and each hydrogen finishes at two.
Model: The remaining 6 electrons sit as three lone pairs on the fluorine, pointing straight out with the dots side by side; the carbon and the hydrogens carry no dots. Check 1: four lines (8) plus three lone pairs (6) = 14 electrons drawn, matching the total. Check 2: the carbon counts its four shared pairs = 8; the fluorine counts one shared pair plus three lone pairs = 8; each hydrogen counts its one shared pair = 2. Both checks pass, so step 5 (conversion) is not needed.
Full model answer. (a) carbon: 1 atom × 4 valence electrons = 4; hydrogen: 3 atoms × 1 = 3; fluorine: 1 atom × 7 = 7. Total = 4 + 3 + 7 = 14 valence electrons.
(b) Carbon is the central atom because it can form the most bonds — four, while hydrogen and fluorine each form one. The skeleton is the carbon in the middle joined by single lines to the three hydrogens and the fluorine: four lines, using 8 of the 14 electrons.
(c) The remaining 6 electrons sit as three lone pairs on the fluorine, pointing straight out with the dots side by side; the carbon and the hydrogens carry no dots. Check 1: four lines (8) plus three lone pairs (6) = 14 electrons drawn, matching the total. Check 2: the carbon counts its four shared pairs = 8; the fluorine counts one shared pair plus three lone pairs = 8; each hydrogen counts its one shared pair = 2. Both checks pass, so step 5 (conversion) is not needed.
End of Topic Test: Electron groups and shape & Classifying and drawing shapes & Bond polarity & Molecular polarity (u05-t2 · 5 forms × 21 items · 105 total)
David's notes for James:
STRUCTURAL ADJUDICATION 'covalent nonmetal vocabulary' (confirm): this gate's topics are the shapes and polarity of molecules built from the small classroom-safe covalent nonmetal set, and the taught electronegativity comparisons NAME those elements as facts (C-H is the taught nonpolar pair, F is the taught record holder, O-vs-S the taught contrast, ...) - so V-T7's cross-slot substance exclusivity is structurally unsatisfiable for that vocabulary over 21 rows x 5 forms. Everything text-fixable WAS content-fixed first (58 stage-3 patch ops: all 44 spec-text gram reuses, 35 cross-form gram reuses, 10 same-seq instance grams and 10 adjacency lines reworded/re-instanced; element names trimmed to SYMBOL notation wherever the case allows - the word 'carbon' fell 42 -> 13 slots gate-wide). The irreducible residue (150 fail lines, all in the four excusable kinds) is covered by 10 recorded adjudicated_instance_families in gate_config.json (9 element-name families: carbon/hydrogen/oxygen/fluorine/chlorine/sulfur/nitrogen/iodine/phosphorus, each with slots + rationale, + the group-numbers-15/16/17 tokens at the two from-formula stems), enforced by the gate-local validate_with_adjudications.py wrapper over the untouched _shared validator (U2-G2/U3-G2 precedent). Retake leakage between forms is the accepted cost - flag if any family should be redistributed.
STALE specNotes FLAG (CMB-028): your v2 spec fix is IN and verified at seed placement - pool 12 (PH₃) keys 'Trigonal pyramidal' with substantive distractors, and A#8 is that gate item essentially verbatim - but CMB-028's specNotes still describe the OLD None-of-the-above design. Our authoritative QC model objected to A#8 on the strength of those specNotes; recorded as a course-local-authority override (the v2 spec item wins). Please refresh the specNotes text.
NOTA REPLACEMENTS (3 seed seats, opportunistic rule ANSWERS #2): pool 13 (B#8, CHCl₃ tetrahedral) fourth seat 'None of the above.' -> 'Trigonal pyramidal' with a lone-pair-miscount misconception; pool 36 (A#13) and pool 37 (B#13) fourth seats -> 'A metallic bond', misconception-keyed to the metal-category confusion using the prior-taught CMB-004 category (authored D#13/E#13 carry the same fourth seat for parallelism). Our QC model maintains 'A metallic bond' sits outside CMB-036's fixed three-way option set - recorded override; confirm the seat or supply a preferred fourth misconception.
SEED PATCH - C#18 RETARGETED (confirm): your CMB-030 panel gate item (C#10) and CMB-032 panel gate item (C#18) landed on the SAME form with byte-identical stems and keys ('Which panel shows a bent molecule?' / Panel A). C#18 now asks for the LINEAR panel (key Panel D, CSe₂ - CMB-032's own multiple-bonds-count-once transfer case); panel set and figure kept VERBATIM; distractor misconceptions rewritten for the new target.
SEED INSTANCE FRESHENINGS (SEED RULING - seeds get no freshness exemption; structures, keys and misconception logic verbatim throughout): NF₃->SbBr₃ (pool 10; NF₃'s owner is the seq-12 image row), H₂O->TeBr₂ (pool 14; H₂O is CMB-028's own corpus), panel members on pools 8/16/19 (NF₃->NH₂Cl, CH₄->CI₄, AsCl₃->SbH₃, SiH₄->GeI₄, CO₂->ICN, PH₃->SbF₃, SiF₄->SnCl₄), AsCl₃->AsBr₃ (pool 22), HFCO->F₂CS (pool 24), OCS->CSe₂ (pool 25), O–F->Se–O (pool 40), Cl₂O->TeCl₂ (pool 51 option b; Cl₂O is CMB-041's own fluency corpus), CH₄->C₂H₆ + F₂->O₂ (pool 53 options), CS₂->BrCN (pool 32 FRQ; CS₂ owns form A's seq-5 numeric slot). QC-driven swaps on top: A#20 CCl₄->SiBr₄ (memory-answerable against CMB-040's worked example), C#19 supplied-label swaps SbI₃->NF₃ / SeBr₂->H₂S (same-central-family giveaway fix), E#20 BrCl->HBr (onto a 'noticeably' polar bond per CMB-036's banding).
FRQ DESIGN (confirm the typed conversion): your two CMB-034 gate PRODUCTIONS (draw-from-formula) are delivered as TYPED 3-part FRQs - (a) total the valence electrons with arithmetic (25), (b) describe the completed Lewis diagram in words: bonds, lone-pair placement, central-atom lone pair (40), (c) name the shape and justify from the two counts (35); rubric sums 100, parts split losslessly. Instances rotate the five taught shape outcomes: A CF₂Cl₂ (your pool 30 verbatim), B BrCN (your pool 32 with CS₂ freshened, linear via multiple bonds), C PBr₃ (trigonal pyramidal), D SCl₂ (bent), E CH₂Br₂ (mixed-partner tetrahedral). Typed answers never need sub/superscripts - the formula is printed in the stem and answers are counts + words. Standing typed-plan flag applies.
NUMERIC ROWS (CMB-025, seqs 5-6 on every form): count-from-Lewis-figure items; answers are exact small integers (2-4), unit 'groups' (your seed convention), integer:true, sigFigs display-only; every numeric item carries wrongValueDiagnostics (multiple-bond-counted-twice / outer-atom-lone-pairs-counted / bonds-only miscount classes) exported from the authored misconceptions.
COURSE FIVE-SHAPE TABLE RESPECTED (authoring constraint, confirm): no item keys a shape outside the taught five (no AX₂E₁ 'bent-from-three-groups' items - NOCl appears only inside a seq-6 electron-group COUNT, never as a shape call); NI₃ and phosgene were excluded from fresh instances; lexicon-listed elements are written as formulas/symbols in scanned fields (exported as Unicode subscripts), with element NAMES only where the case itself requires the word.
PACKAGING-TIME FORMULA-REGISTER SWEEP (new deterministic check, adopted from the U5-G1 packaging sibling; _packaging_instance_sweep.py/.json): the shared V-T7 scan works in the WORD register and is architecturally blind to instances written only as formulas (CS₂, PH₃, CF₂Cl₂). The sweep re-checked every molecule token in every student-facing field against the STUDENT-SEEN scope corpus. Banned-instance re-sweep (words + formula SYMBOLS, widened U3-G3 form): 0 hits bank-wide. Formula-register triage: 36 slots hit student-seen scope text; all but two are your own seed instances / the recorded standing-WARN ledger (SiF₄, OF₂, H₂S, CS₂, C₂H₄, SCl₂, PH₃, CBr₄, CF₄, OCS, HCN, H₂CO, GeCl₄, NF₃) or tokenizer noise ('tetrahedron'/'direction' are course vocabulary, not instances). TWO flagged memory-answerability candidates for adjudication, NOT content-fixed at packaging (any edit would re-open the QC loop): B#17 ('work out the shape of CCl₄' -> Tetrahedral; CMB-040's worked example shows CCl₄ WITH 'the tetrahedral shape' named in a student-seen line - the same class that got A#20 content-fixed at blind) and B#20 (SiF₄ skipped-step critique -> nonpolar; CMB-041's OWN worked example performs exactly that classification - matches the recorded-ACCEPTED D#17/D#21 own-WE precedent, so it may stand). Proposed remedy if you or David rule them memory-answerable: fresh-instance swaps (e.g. B#17 CCl₄ -> GeBr₄) followed by re-validation + re-blind + re-sol of the changed items.
Blind-review figure families 'lewis-diagram' / 'shape-diagram' / 'lewis-panels' were rendered with full drawn content by a gate-local packet augmenter (augment_blind_figs.py; reproduces the seeded option shuffle); documented as a _shared make_blind_packet.py candidate for the maintainer, not applied this wave (_shared read-only). Same status for the extra_task_idioms derivation misses: 5 of the 7 recorded idioms are statement-clause or gateItem-sourced task idioms the automatic A2 derivation cannot currently harvest.
RECORDED CONSTRUCT OVERRIDES (our authoritative QC model + one blind reviewer maintain objections; course-local authority applied, David's sign-off pending): (1) A#8 keys 'Trigonal pyramidal' per your v2 spec (stale-specNotes note above); (2) C#12/E#12 shape-DIAGRAM items draw multiple bonds as plain single lines - CMB-033 rule line 1 defines a shape diagram as atom symbols joined by PLAIN LINES with the name beneath, and its specNotes fix 'atoms-only, plain lines' for determinism (the multiple-bond-line drawings are wrong shape diagrams BY the taught definition); (3) E#12 (and the seq-12 row generally) is an image-option MCQ standing in for CMB-033's drawing-production design - the test medium cannot deliver drawing production (typed/MCQ contract), and A#12 is your own sanctioned NF₃ image-option gate MCQ; (4) E#13/B#13/D#13 'A metallic bond' seat (note 3). Flag any you want reworked instead.
FRQ delivery: your `prod` draw-on-paper class is delivered as a typed diagram-PLAN task (state kinds/recipes/counts/spacing; rubric grades the same observables). Confirm this mapping (pending from the U01-G1 round-trip).
full notes file
# u05-t2 — notes/queries from David's side (U5-G2)
1. STRUCTURAL ADJUDICATION 'covalent nonmetal vocabulary' (confirm): this gate's topics are the shapes and polarity of molecules built from the small classroom-safe covalent nonmetal set, and the taught electronegativity comparisons NAME those elements as facts (C-H is the taught nonpolar pair, F is the taught record holder, O-vs-S the taught contrast, ...) - so V-T7's cross-slot substance exclusivity is structurally unsatisfiable for that vocabulary over 21 rows x 5 forms. Everything text-fixable WAS content-fixed first (58 stage-3 patch ops: all 44 spec-text gram reuses, 35 cross-form gram reuses, 10 same-seq instance grams and 10 adjacency lines reworded/re-instanced; element names trimmed to SYMBOL notation wherever the case allows - the word 'carbon' fell 42 -> 13 slots gate-wide). The irreducible residue (150 fail lines, all in the four excusable kinds) is covered by 10 recorded adjudicated_instance_families in gate_config.json (9 element-name families: carbon/hydrogen/oxygen/fluorine/chlorine/sulfur/nitrogen/iodine/phosphorus, each with slots + rationale, + the group-numbers-15/16/17 tokens at the two from-formula stems), enforced by the gate-local validate_with_adjudications.py wrapper over the untouched _shared validator (U2-G2/U3-G2 precedent). Retake leakage between forms is the accepted cost - flag if any family should be redistributed.
2. STALE specNotes FLAG (CMB-028): your v2 spec fix is IN and verified at seed placement - pool 12 (PH₃) keys 'Trigonal pyramidal' with substantive distractors, and A#8 is that gate item essentially verbatim - but CMB-028's specNotes still describe the OLD None-of-the-above design. Our authoritative QC model objected to A#8 on the strength of those specNotes; recorded as a course-local-authority override (the v2 spec item wins). Please refresh the specNotes text.
3. NOTA REPLACEMENTS (3 seed seats, opportunistic rule ANSWERS #2): pool 13 (B#8, CHCl₃ tetrahedral) fourth seat 'None of the above.' -> 'Trigonal pyramidal' with a lone-pair-miscount misconception; pool 36 (A#13) and pool 37 (B#13) fourth seats -> 'A metallic bond', misconception-keyed to the metal-category confusion using the prior-taught CMB-004 category (authored D#13/E#13 carry the same fourth seat for parallelism). Our QC model maintains 'A metallic bond' sits outside CMB-036's fixed three-way option set - recorded override; confirm the seat or supply a preferred fourth misconception.
4. SEED PATCH - C#18 RETARGETED (confirm): your CMB-030 panel gate item (C#10) and CMB-032 panel gate item (C#18) landed on the SAME form with byte-identical stems and keys ('Which panel shows a bent molecule?' / Panel A). C#18 now asks for the LINEAR panel (key Panel D, CSe₂ - CMB-032's own multiple-bonds-count-once transfer case); panel set and figure kept VERBATIM; distractor misconceptions rewritten for the new target.
5. SEED INSTANCE FRESHENINGS (SEED RULING - seeds get no freshness exemption; structures, keys and misconception logic verbatim throughout): NF₃->SbBr₃ (pool 10; NF₃'s owner is the seq-12 image row), H₂O->TeBr₂ (pool 14; H₂O is CMB-028's own corpus), panel members on pools 8/16/19 (NF₃->NH₂Cl, CH₄->CI₄, AsCl₃->SbH₃, SiH₄->GeI₄, CO₂->ICN, PH₃->SbF₃, SiF₄->SnCl₄), AsCl₃->AsBr₃ (pool 22), HFCO->F₂CS (pool 24), OCS->CSe₂ (pool 25), O–F->Se–O (pool 40), Cl₂O->TeCl₂ (pool 51 option b; Cl₂O is CMB-041's own fluency corpus), CH₄->C₂H₆ + F₂->O₂ (pool 53 options), CS₂->BrCN (pool 32 FRQ; CS₂ owns form A's seq-5 numeric slot). QC-driven swaps on top: A#20 CCl₄->SiBr₄ (memory-answerable against CMB-040's worked example), C#19 supplied-label swaps SbI₃->NF₃ / SeBr₂->H₂S (same-central-family giveaway fix), E#20 BrCl->HBr (onto a 'noticeably' polar bond per CMB-036's banding).
6. FRQ DESIGN (confirm the typed conversion): your two CMB-034 gate PRODUCTIONS (draw-from-formula) are delivered as TYPED 3-part FRQs - (a) total the valence electrons with arithmetic (25), (b) describe the completed Lewis diagram in words: bonds, lone-pair placement, central-atom lone pair (40), (c) name the shape and justify from the two counts (35); rubric sums 100, parts split losslessly. Instances rotate the five taught shape outcomes: A CF₂Cl₂ (your pool 30 verbatim), B BrCN (your pool 32 with CS₂ freshened, linear via multiple bonds), C PBr₃ (trigonal pyramidal), D SCl₂ (bent), E CH₂Br₂ (mixed-partner tetrahedral). Typed answers never need sub/superscripts - the formula is printed in the stem and answers are counts + words. Standing typed-plan flag applies.
7. NUMERIC ROWS (CMB-025, seqs 5-6 on every form): count-from-Lewis-figure items; answers are exact small integers (2-4), unit 'groups' (your seed convention), integer:true, sigFigs display-only; every numeric item carries wrongValueDiagnostics (multiple-bond-counted-twice / outer-atom-lone-pairs-counted / bonds-only miscount classes) exported from the authored misconceptions.
8. COURSE FIVE-SHAPE TABLE RESPECTED (authoring constraint, confirm): no item keys a shape outside the taught five (no AX₂E₁ 'bent-from-three-groups' items - NOCl appears only inside a seq-6 electron-group COUNT, never as a shape call); NI₃ and phosgene were excluded from fresh instances; lexicon-listed elements are written as formulas/symbols in scanned fields (exported as Unicode subscripts), with element NAMES only where the case itself requires the word.
9. PACKAGING-TIME FORMULA-REGISTER SWEEP (new deterministic check, adopted from the U5-G1 packaging sibling; _packaging_instance_sweep.py/.json): the shared V-T7 scan works in the WORD register and is architecturally blind to instances written only as formulas (CS₂, PH₃, CF₂Cl₂). The sweep re-checked every molecule token in every student-facing field against the STUDENT-SEEN scope corpus. Banned-instance re-sweep (words + formula SYMBOLS, widened U3-G3 form): 0 hits bank-wide. Formula-register triage: 36 slots hit student-seen scope text; all but two are your own seed instances / the recorded standing-WARN ledger (SiF₄, OF₂, H₂S, CS₂, C₂H₄, SCl₂, PH₃, CBr₄, CF₄, OCS, HCN, H₂CO, GeCl₄, NF₃) or tokenizer noise ('tetrahedron'/'direction' are course vocabulary, not instances). TWO flagged memory-answerability candidates for adjudication, NOT content-fixed at packaging (any edit would re-open the QC loop): B#17 ('work out the shape of CCl₄' -> Tetrahedral; CMB-040's worked example shows CCl₄ WITH 'the tetrahedral shape' named in a student-seen line - the same class that got A#20 content-fixed at blind) and B#20 (SiF₄ skipped-step critique -> nonpolar; CMB-041's OWN worked example performs exactly that classification - matches the recorded-ACCEPTED D#17/D#21 own-WE precedent, so it may stand). Proposed remedy if you or David rule them memory-answerable: fresh-instance swaps (e.g. B#17 CCl₄ -> GeBr₄) followed by re-validation + re-blind + re-sol of the changed items.
10. Blind-review figure families 'lewis-diagram' / 'shape-diagram' / 'lewis-panels' were rendered with full drawn content by a gate-local packet augmenter (augment_blind_figs.py; reproduces the seeded option shuffle); documented as a _shared make_blind_packet.py candidate for the maintainer, not applied this wave (_shared read-only). Same status for the extra_task_idioms derivation misses: 5 of the 7 recorded idioms are statement-clause or gateItem-sourced task idioms the automatic A2 derivation cannot currently harvest.
11. RECORDED CONSTRUCT OVERRIDES (our authoritative QC model + one blind reviewer maintain objections; course-local authority applied, David's sign-off pending): (1) A#8 keys 'Trigonal pyramidal' per your v2 spec (stale-specNotes note above); (2) C#12/E#12 shape-DIAGRAM items draw multiple bonds as plain single lines - CMB-033 rule line 1 defines a shape diagram as atom symbols joined by PLAIN LINES with the name beneath, and its specNotes fix 'atoms-only, plain lines' for determinism (the multiple-bond-line drawings are wrong shape diagrams BY the taught definition); (3) E#12 (and the seq-12 row generally) is an image-option MCQ standing in for CMB-033's drawing-production design - the test medium cannot deliver drawing production (typed/MCQ contract), and A#12 is your own sanctioned NF₃ image-option gate MCQ; (4) E#13/B#13/D#13 'A metallic bond' seat (note 3). Flag any you want reworked instead.
A student explains the even spacing of the four fluorines of SiF₄ this way: 'The fluorine atoms attract each other equally, and the equal attraction spaces them out.' What is wrong with the explanation?
The spacing comes from repulsion between the electron groups, which take positions as far apart as possible — not from attraction between the outer atoms. KEY
Nothing is wrong — outer atoms really do attract one another, and that equal attraction is exactly what spaces the four bonds evenly around the silicon.
The only error is the atom — it is the silicon that attracts the four fluorines equally and holds them apart.
The explanation fails only because F atoms are too small to attract one another.
The figure shows the Lewis diagram of ethyne, H–C≡C–H. Each carbon has two electron groups and no lone pairs. Which description fits the real molecule?
FIGURE (lewis-diagram · stimulus) — molecule: "C₂H₂" · structure: "H–C≡C–H in a row; triple lines between the carbons; no lone pairs" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₂H₂",
"structure": "H–C≡C–H in a row; triple lines between the carbons; no lone pairs",
"style": "clean textbook Lewis diagram"
}
}
All four atoms lie in one straight line. KEY
The four atoms sit at the corners of a square.
The two hydrogens bend to the same side, giving the molecule a U shape.
The hydrogens stick out at right angles to the carbon–carbon bond.
The figure shows the Lewis diagram of CS₂. How many electron groups surround the C atom?
FIGURE (lewis-diagram · stimulus) — molecule: "CS₂" · structure: "S=C=S with double lines on each side; two radial lone pairs on each S" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CS₂",
"structure": "S=C=S with double lines on each side; two radial lone pairs on each S",
"style": "clean textbook Lewis diagram"
}
}
Answer: 2 groups KEY
also accepted: 2 groups
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted each double bond as two groups — a bond of any multiplicity counts once",
"feedback": null
},
{
"value": 6,
"misconception": "you added the sulfurs' lone pairs — outer-atom lone pairs never count at the central atom",
"feedback": null
},
{
"value": 8,
"misconception": "you counted electrons around the carbon instead of groups",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the carbon: two C=S double bonds = 2 groups. Each double bond counts once, and the sulfurs' lone pairs belong to the sulfurs. 2 + 0 = 2 electron groups."
}
The figure shows the Lewis diagram of SCl₂. How many electron groups surround the S atom?
FIGURE (lewis-diagram · stimulus) — molecule: "SCl₂" · structure: "S central; single lines S–Cl to each side; two radial lone pairs on S; three radial lone pairs on each Cl" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SCl₂",
"structure": "S central; single lines S–Cl to each side; two radial lone pairs on S; three radial lone pairs on each Cl",
"style": "clean textbook Lewis diagram"
}
}
Answer: 4 groups KEY
also accepted: 4 groups
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted only the bonds — the sulfur's two lone pairs each count as one group",
"feedback": null
},
{
"value": 10,
"misconception": "you added the chlorines' lone pairs — outer-atom lone pairs never count at the central atom",
"feedback": null
},
{
"value": 8,
"misconception": "you counted electrons around the sulfur instead of groups",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the sulfur: two S–Cl single bonds = 2 groups. Lone pairs on the sulfur: two = 2 groups; the chlorines' pairs belong to the chlorines. 2 + 2 = 4 electron groups."
}
The figure shows the Lewis diagram of PBr₃. Classify its shape.
FIGURE (lewis-diagram · stimulus) — molecule: "PBr₃" · layout: "P central; three single bonds to Br at left, right, and below; one lone pair on P pointing up; three lone pairs on each Br radially outward" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PBr₃",
"layout": "P central; three single bonds to Br at left, right, and below; one lone pair on P pointing up; three lone pairs on each Br radially outward",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
The figure shows the Lewis diagram of H₂Te. Classify its shape.
FIGURE (lewis-diagram · stimulus) — molecule: "H₂Te" · layout: "Te central; single bonds to two H at lower left and lower right; two lone pairs on Te pointing up-left and up-right" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "H₂Te",
"layout": "Te central; single bonds to two H at lower left and lower right; two lone pairs on Te pointing up-left and up-right",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
A student writes: 'AsBr₃ has four electron groups, so its real shape is tetrahedral — trigonal pyramidal is just a nickname for it.' What is wrong with the claim?
Nothing is hidden — the four atoms genuinely form a pyramid, and shape names report atom positions only, so trigonal pyramidal IS the shape. KEY
Nothing is wrong — a molecule with four electron groups is always tetrahedral.
The claim fails only because AsBr₃ has three electron groups, not four.
The claim fails because the lone pair pushes the three Br atoms so far apart that no single shape name can describe the molecule.
The figure shows the Lewis diagram of NF₃: three N–F bonds and one lone pair on the N atom. Which drawing is the correct shape diagram of NF₃?
FIGURE (lewis-diagram · stimulus) — molecule: "NF₃" · structure: "N central; three single lines N–F; one radial lone pair on N; three radial lone pairs on each F" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "NF₃",
"structure": "N central; three single lines N–F; one radial lone pair on N; three radial lone pairs on each F",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
},
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "NF₃",
"layout": "N at the peak, three F at the corners of a low tripod below, plain bond lines, name label 'trigonal pyramidal' beneath",
"style": "clean textbook shape diagram, atoms only"
}
},
{
"option": "d1",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "NF₃",
"layout": "N at the center of a flat triangle with the three F at its corners, name label 'trigonal planar' beneath",
"style": "clean textbook shape diagram, atoms only"
}
},
{
"option": "d2",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "NF₃",
"layout": "N central with three F as a low tripod below and a fourth circle drawn straight up where the lone pair sits, name label 'tetrahedral' beneath",
"style": "clean textbook shape diagram with an extra non-atom circle"
}
},
{
"option": "d3",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "NF₃",
"layout": "F, N, F, F drawn along one straight line, name label 'linear' beneath",
"style": "clean textbook shape diagram, atoms only"
}
}
]
}
Drawing: N at the peak with the three F at the corners of a low tripod below, plain bond lines, name label 'trigonal pyramidal' beneath. KEY
Drawing: N at the center of a flat triangle with the three F at its corners, name label 'trigonal planar' beneath.
Drawing: N with three F as a low tripod below and a fourth circle drawn straight up where the lone pair sits, name label 'tetrahedral' beneath.
Drawing: F, N, F, F along one straight line, name label 'linear' beneath.
CMB-036 · medium · application · seq 13 · seed:U5-G2.pool[36] (CMB-036 gateItems, James) | NOTA option d replaced with misconception-keyed 'A metallic bond' (flag replace_distractor) · mcq4
Sodium is a metal and bromine is a nonmetal, and their electronegativity difference is very large. Classify the bond in NaBr.
An ionic bond KEY
A polar covalent bond
A nonpolar covalent bond
A metallic bond
CMB-037 · medium · application · seq 14 · seed:U5-G2.pool[39] (CMB-037 gateItems, James) | swap-distractor reworded 'O is δ+, S is δ−' -> 'S is δ−, O is δ+' (same claim; V-T3 dedup normalization strips δ/+/− so the mirrored text normalized identical to the key) · mcq4
Oxygen is more electronegative than sulfur. Which labels are correct for the S–O bond?
A student reads the δ− on the chlorine of a C–Cl bond and says, 'That means the chlorine has taken the shared electrons completely.' What is the correct account?
The chlorine only holds the shared electrons CLOSER — they stay in the bond, leaving the chlorine end slightly negative and the carbon end slightly positive. KEY
The student is right — δ− marks an atom that has gained a whole electron.
The student is almost right — the chlorine takes the electrons completely, but only for half of the time, handing them back in between.
The δ− has nothing to do with the shared electrons — it marks chlorine's group in the periodic table.
A student says CBr₄ must be polar 'because it contains four polar bonds, and four is a lot.' CBr₄ is tetrahedral with four identical C–Br bonds. What is the correct verdict and reason?
Nonpolar — equal pulls in opposite directions cancel, leaving no overall pull, however many bonds there are. KEY
Polar — with four polar bonds, there is simply too much combined pull for any shape to cancel.
Nonpolar — because C–Br bonds are too weak to count as polar.
Polar — every molecule that contains bromine is polar.
Starting from its formula, work out the shape of SbCl₃. Antimony sits in Group 15; chlorine sits in Group 17.
Trigonal pyramidal KEY
Trigonal planar
Tetrahedral
Linear
CMB-032 · hard · transfer · seq 18 · seed:U5-G2.pool[24] (CMB-032 gateItems, James) | instance freshened HFCO->F₂CS (flag must_freshen_instance: HFCO owner = seq 7); all fields swept · mcq4
The figure shows the Lewis diagram of thiocarbonyl fluoride, F₂CS — its central C atom forms one double bond to S and a single bond to each F. Classify its shape.
FIGURE (lewis-diagram · stimulus) — molecule: "F₂CS" · layout: "C central; double bond up to S; single bonds lower-left and lower-right to F; no lone pair on C; two lone pairs on S and three on each F radially outward" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "F₂CS",
"layout": "C central; double bond up to S; single bonds lower-left and lower-right to F; no lone pair on C; two lone pairs on S and three on each F radially outward",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Trigonal planar KEY
Tetrahedral
Trigonal pyramidal
Bent
CMB-041 · hard · transfer · seq 19 · seed:U5-G2.pool[51] (CMB-041 gateItems, James, demo-gate curated) | option b freshened Cl₂O->TeCl₂ (flag must_freshen_instance: Cl₂O is CMB-041's own fluency corpus); stem gains the tellurium pull clause; feedback logic unchanged · mcq4
Chlorine out-pulls Ge, As, Te, and H; iodine out-pulls H. Which of these molecules is nonpolar?
In SiBr₄, the pull of each Si–Br bond is toward the Br end. A student classifies the molecule as polar 'because each bond is polar.' Which step of the routine did the student skip, and what is the correct verdict?
The shape step — the four identical pulls cancel in the symmetric tetrahedral arrangement, so the molecule is nonpolar. KEY
No step — polar bonds are the whole test, so the molecule is polar.
The bond step — Si–Br bonds are nonpolar, so the molecule has nothing to cancel.
The shape step — and the tetrahedral shape makes the pulls add up, so the molecule is even more polar.
CMB-034 · medium · application · seq 21 · seed:U5-G2.pool[30] (= CMB-034 gateItems[0] production, James demo-gate) — drawing prod converted to the typed three-part routine per the blueprint FRQ contract; model arithmetic, halogen lone-pair placement, and the mixed-outer-atoms teaching point carried from the seed model/checklist verbatim in substance | stage-2 fix pass (_authoring_d): V-T12 typed-model fix · frq
Work out the shape of CF₂Cl₂ from its formula; C is the central atom. Type your reasoning in three parts:
Work out the shape of CF₂Cl₂ from its formula; C is the central atom. Type your reasoning in three parts:
(a) Total the valence electrons in the molecule, showing the arithmetic.
(b) Describe the completed Lewis diagram in words: the bonds the central atom makes, where the remaining electrons sit as lone pairs, and whether the central atom keeps a lone pair.
(c) Name the molecule's shape, and justify the name from the routine's two counts — the electron groups and the lone pairs on the central atom.
Part a. Total the valence electrons in the molecule, showing the arithmetic.
Part b. Describe the completed Lewis diagram in words: the bonds the central atom makes, where the remaining electrons sit as lone pairs, and whether the central atom keeps a lone pair.
Model: The carbon is central with two C–F and two C–Cl single bonds, using 8 electrons; the remaining 24 sit as three lone pairs on each halogen; the carbon holds no lone pair.
Part c. Name the molecule's shape, and justify the name from the routine's two counts — the electron groups and the lone pairs on the central atom.
Model: Four electron groups with no lone pair on the carbon — the molecule is tetrahedral. Mixing two kinds of outer atom does not change the four-group, no-lone-pair count.
Full model answer. (a) Total: 4 + 2 × 7 + 2 × 7 = 32 valence electrons.
(b) The carbon is central with two C–F and two C–Cl single bonds, using 8 electrons; the remaining 24 sit as three lone pairs on each halogen; the carbon holds no lone pair.
(c) Four electron groups with no lone pair on the carbon — the molecule is tetrahedral. Mixing two kinds of outer atom does not change the four-group, no-lone-pair count.
The figure shows the Lewis diagram of H₂S. A student classifies it as linear, arguing that only two atoms are attached to the sulfur. Why is the student wrong?
FIGURE (lewis-diagram · stimulus) — molecule: "H₂S" · structure: "S central; two single lines S–H; two radial lone pairs on S" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "H₂S",
"structure": "S central; two single lines S–H; two radial lone pairs on S",
"style": "clean textbook Lewis diagram"
}
}
The two lone pairs on the S atom also count as electron groups, so the sulfur has four groups — H₂S fails the linear condition. KEY
The student miscounted the atoms — H₂S has three atoms, and linear molecules can only ever have two.
The student is wrong only because sulfur atoms are too large to sit in a straight line with two hydrogens.
Nothing is wrong — two attached atoms always make a molecule linear.
The figure shows the Lewis diagram of C₂H₄. How many electron groups surround the left C atom?
FIGURE (lewis-diagram · stimulus) — molecule: "C₂H₄" · structure: "C=C double lines in the middle; two single lines from each C to H atoms; no lone pairs" · style: "clean textbook Lewis diagram"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₂H₄",
"structure": "C=C double lines in the middle; two single lines from each C to H atoms; no lone pairs",
"style": "clean textbook Lewis diagram"
}
}
Answer: 3 groups KEY
also accepted: 3 groups
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the double bond as two groups — a bond of any multiplicity counts once",
"feedback": null
},
{
"value": 6,
"misconception": "you counted the groups around both carbons — count at one atom at a time",
"feedback": null
},
{
"value": 2,
"misconception": "you skipped the double bond and counted only the C–H bonds",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the left carbon: two C–H single bonds and one C=C double bond = 3 groups. The double bond counts once, and the other carbon's bonds are its own. 3 + 0 = 3 electron groups."
}
CMB-025 · medium · application · seq 6 · authored (wave-4; lone-pairs-count rotation of pool 5's case, fresh instance H₂O₂, formula-only naming) · numeric
The figure shows the Lewis diagram of H₂O₂ (H–O–O–H). How many electron groups surround the left O atom?
FIGURE (lewis-diagram · stimulus) — molecule: "H₂O₂" · structure: "chain H–O–O–H with single lines; two radial lone pairs on each O" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "H₂O₂",
"structure": "chain H–O–O–H with single lines; two radial lone pairs on each O",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 4 groups KEY
also accepted: 4 groups
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted only the bonds — the two lone pairs on the atom each count as one group",
"feedback": null
},
{
"value": 6,
"misconception": "you added the right O atom's lone pairs — count at one atom at a time",
"feedback": null
},
{
"value": 8,
"misconception": "you counted electrons around the atom instead of groups",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the left O atom: one O–H single bond and one O–O single bond = 2 groups. Lone pairs on that atom: two = 2 groups; the right O atom's lone pairs are its own. 2 + 2 = 4 electron groups."
}
The figure shows the Lewis diagram of SbBr₃. A student classifies it as trigonal planar, arguing that three atoms are attached. Why is the student wrong?
FIGURE (lewis-diagram · stimulus) — molecule: "SbBr₃" · structure: "Sb central; three single lines Sb–Br; one radial lone pair on Sb; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SbBr₃",
"structure": "Sb central; three single lines Sb–Br; one radial lone pair on Sb; three radial lone pairs on each Br",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
The lone pair on the antimony is a fourth electron group, so the antimony has four groups — SbBr₃ fails the trigonal planar condition. KEY
The student is wrong only because the three attached atoms are halogens, and halogens never sit at a triangle's corners.
The student miscounted — three Br atoms plus the antimony makes four atoms, and four-atom molecules cannot be flat.
Nothing is wrong — three attached atoms always make a molecule trigonal planar.
CMB-028 · medium · application · seq 8 · seed:U5-G2.pool[13] (CMB-028 gateItems, James) | NOTA option d replaced with misconception-keyed 'Trigonal pyramidal' (flag replace_distractor) · mcq4
The figure shows the Lewis diagram of chloroform, CHCl₃. Classify the shape of the molecule.
FIGURE (lewis-diagram · stimulus) — molecule: "CHCl₃" · structure: "C central; one single line C–H; three single lines C–Cl; three radial lone pairs on each Cl" · style: "clean textbook Lewis diagram"raw spec
{
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"molecule": "CHCl₃",
"structure": "C central; one single line C–H; three single lines C–Cl; three radial lone pairs on each Cl",
"style": "clean textbook Lewis diagram"
}
}
Tetrahedral KEY
Trigonal planar
Linear
Trigonal pyramidal
CMB-029 · medium · application · seq 9 · seed:U5-G2.pool[16] (CMB-029 gateItems, James) | panels freshened: AsCl₃->SbH₃ (same-seq, A5), SiH₄->GeI₄ (same-form leak vs pool 21), CO₂->ICN (CO₂ owner = seq 19 on this same form); H₂CO kept (James) · mcq4
Panels A to D each show the Lewis diagram of a molecule. Which panel shows a trigonal pyramidal molecule?
FIGURE (lewis-panels · stimulus) — panels: [{"panel": "A", "description": "SbH₃ — Sb central with three single bonds to H and one lone pair on Sb pointing up"}, {"panel": "B", "description": "GeI₄ — G… · style: "clean textbook Lewis panels, boxes labeled A to D in one figure; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-panels",
"panels": [
{
"panel": "A",
"description": "SbH₃ — Sb central with three single bonds to H and one lone pair on Sb pointing up"
},
{
"panel": "B",
"description": "GeI₄ — Ge central with four single bonds to I and no lone pair on Ge; three lone pairs on each I"
},
{
"panel": "C",
"description": "H₂CO — C central with a double bond to O and single bonds to two H, no lone pair on C; two lone pairs on O"
},
{
"panel": "D",
"description": "ICN — I–C≡N in a row; single line I–C, triple lines C–N; three lone pairs on I and one on N; no lone pair on the central C"
}
],
"style": "clean textbook Lewis panels, boxes labeled A to D in one figure; lone pairs radial with the two dots equidistant from the atom"
}
}
Only two chlorine atoms are attached to the selenium in SeCl₂, so a student writes that the three atoms must lie in a straight line. The figure shows the Lewis diagram. What is the correct classification?
FIGURE (lewis-diagram · stimulus) — molecule: "SeCl₂" · layout: "Se central; single bonds to two Cl at lower left and lower right; two lone pairs on Se pointing up-left and up-right; three lone pairs on each Cl radially o… · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SeCl₂",
"layout": "Se central; single bonds to two Cl at lower left and lower right; two lone pairs on Se pointing up-left and up-right; three lone pairs on each Cl radially outward",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Silane, SiH₄, is tetrahedral; phosphine, PH₃, is trigonal pyramidal. Both central atoms hold four electron groups. What makes the two names different?
In PH₃ one of the four groups is a lone pair, and shape names describe only atom positions — so PH₃ is named for its four-atom pyramid. KEY
Both molecules should be tetrahedral, because both central atoms have four electron groups.
The silicon in SiH₄ holds four electron groups but the phosphorus in PH₃ holds only three.
Silicon and phosphorus sit in different groups of the periodic table, and the group number sets the shape's name.
CMB-033 · medium · application · seq 12 · authored (wave-4; drawing-pick rotation of pool 28's case, bent target, instance SBr₂ — cross-form repeat with seq 2 form E, recorded) · mcq4
The figure shows the Lewis diagram of SBr₂: the S atom makes single bonds to two Br atoms and holds two lone pairs. Which drawing is the correct shape diagram of SBr₂?
FIGURE (lewis-diagram · stimulus) — molecule: "SBr₂" · structure: "S central; single lines S–Br to each side; two radial lone pairs on S; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
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"molecule": "SBr₂",
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"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
},
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"style": "clean textbook shape diagram"
}
},
{
"option": "d1",
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}
},
{
"option": "d2",
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"molecule": "SBr₂",
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}
},
{
"option": "d3",
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}
}
]
}
Drawing: S at the point of a wide V with the two Br at its ends, plain bond lines, name label 'bent' beneath. KEY
Drawing: the three atoms in one straight line, name label 'linear' beneath.
Drawing: S with the two Br below and two extra circles drawn where the lone pairs sit, name label 'tetrahedral' beneath.
Drawing: S at the point of a V with the two lone pairs also drawn as dot pairs between the bonds, name label 'bent' beneath.
CMB-036 · medium · application · seq 13 · seed:U5-G2.pool[37] (CMB-036 gateItems, James) | NOTA option d replaced with misconception-keyed 'A metallic bond' (flag replace_distractor) · mcq4
In the S–O bond, the O end pulls the shared electrons noticeably harder than the S end; both elements are nonmetals. Classify the bond.
CF₄ is nonpolar, but swap one F for an H to make CHF₃ and the molecule becomes polar. Why does the swap stop the cancellation?
The four pulls are no longer identical — a C–H pull differs from a C–F pull — and only equal pulls in opposite directions cancel. KEY
The swap bends the molecule out of its symmetric tetrahedral shape, and bent molecules can never cancel their pulls.
The H atom adds an extra lone pair that unbalances the molecule.
The molecule becomes charged overall, like an ion.
CMB-034 · hard · transfer · seq 17 · authored (wave-4; formula-to-shape rotation of the demo case, instance CCl₄ — cross-form repeat with the seq-20 form-A demo, recorded; no same-form reuse) · mcq4
Starting from its formula, work out the shape of CCl₄.
Tetrahedral KEY
Trigonal pyramidal
Trigonal planar
Linear
CMB-032 · hard · transfer · seq 18 · seed:U5-G2.pool[25] (CMB-032 gateItems, James) | instance freshened OCS->CSe₂ (flag must_freshen_instance: OCS owner = seq 16; CSe₂ same-seq with pool 26 panel D, A5); all fields swept · mcq4
The figure shows the Lewis diagram of CSe₂ — the central C atom makes a double bond to each of its two Se atoms. Classify its shape.
FIGURE (lewis-diagram · stimulus) — molecule: "CSe₂" · layout: "C central; double bond left to Se; double bond right to Se; no lone pair on C; two lone pairs on each Se radially outward" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
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"figureShape": "stimulus",
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"figureType": "lewis-diagram",
"molecule": "CSe₂",
"layout": "C central; double bond left to Se; double bond right to Se; no lone pair on C; two lone pairs on each Se radially outward",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Linear KEY
Bent
Tetrahedral
Trigonal planar
CMB-041 · hard · transfer · seq 19 · seed:U5-G2.pool[53] (CMB-041 gateItems, James, demo-gate curated) | options freshened CH₄->C₂H₆, F₂->O₂ (flag must_freshen_instance: both are CMB-041's own fluency corpus); CO₂ kept as the essential cancel contrast (owner seq 19) · mcq4
In each bond below, the pull on the shared electrons is toward the atom named second; a C–H bond has almost no pull either way: C–N (toward N), C–O (toward O). Which of these molecules is polar?
HCN KEY
CO₂
C₂H₆
O₂
CMB-041 · hard · transfer · seq 20 · authored (wave-4; skipped-step rotation of the demo case, instance SiF₄ — cross-form repeat with seq 1 form A, recorded; no same-form reuse) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
In SiF₄, the pull of each Si–F bond is toward the F end. A student classifies the molecule as polar 'because each bond is polar.' Which step of the routine did the student skip, and what is the correct verdict?
The shape step — SiF₄'s four identical pulls cancel in the symmetric tetrahedral shape, so the molecule is nonpolar. KEY
The bond step — Si–F bonds are actually nonpolar, so the polarity question never even arises for this molecule.
No step — polar bonds always make a polar molecule.
The lone-pair step — the F atoms' lone pairs make the molecule polar.
CMB-034 · medium · application · seq 21 · seed:U5-G2.pool[32] (= CMB-034 gateItems[2] production, James demo-gate) structure — the lone-pair-conversion case — with the INSTANCE freshened CS₂ -> BrCN (flag must_freshen_instance: CS₂ owns seq 5 on form A; one-molecule-one-seq ledger); arithmetic and checklist observables re-derived for BrCN · frq
Work out the shape of BrCN from its formula; the atoms bond in the order Br–C–N, with the carbon in the middle; the Br–C bond stays single. You will need to convert lone pairs into extra shared pairs. Type your reasoning in three parts:
Work out the shape of BrCN from its formula; the atoms bond in the order Br–C–N, with the carbon in the middle; the Br–C bond stays single. You will need to convert lone pairs into extra shared pairs. Type your reasoning in three parts:
(a) Total the valence electrons in the molecule, showing the arithmetic.
(b) Describe the completed Lewis diagram in words: where single bonds fall short, which lone pairs you converted into shared pairs, what multiplicity each bond ends at, and where the lone pairs sit.
(c) Name the shape at the carbon, and justify the name from the routine's two counts.
Part a. Total the valence electrons in the molecule, showing the arithmetic.
Model: Total: 7 + 4 + 5 = 16 valence electrons.
Part b. Describe the completed Lewis diagram in words: where single bonds fall short, which lone pairs you converted into shared pairs, what multiplicity each bond ends at, and where the lone pairs sit.
Model: Single bonds Br–C–N use 4 electrons; completing the outer atoms' octets uses the remaining 12, but the carbon's octet falls short. Convert two lone pairs from the N atom into extra shared pairs: Br–C≡N — a single bond and a triple bond — with three lone pairs left on the Br atom and one on the N atom; the carbon holds none.
Part c. Name the shape at the carbon, and justify the name from the routine's two counts.
Model: The carbon holds two electron groups — the single bond and the triple bond count once each — and no lone pair. Two groups with no lone pair: BrCN is linear.
Full model answer. (a) Total: 7 + 4 + 5 = 16 valence electrons.
(b) Single bonds Br–C–N use 4 electrons; completing the outer atoms' octets uses the remaining 12, but the carbon's octet falls short. Convert two lone pairs from the N atom into extra shared pairs: Br–C≡N — a single bond and a triple bond — with three lone pairs left on the Br atom and one on the N atom; the carbon holds none.
(c) The carbon holds two electron groups — the single bond and the triple bond count once each — and no lone pair. Two groups with no lone pair: BrCN is linear.
Each picture shows a Lewis diagram. Which molecule is linear?
FIGURE (figure · ) — see raw specraw spec
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"optionFigureSpecs": [
{
"option": "key",
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"figureType": "lewis-diagram",
"molecule": "ClCN",
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"style": "clean textbook Lewis diagram, no text labels beyond element symbols"
}
},
{
"option": "d1",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "HOCl",
"drawing": "H–O–Cl in a row with single lines; two radial lone pairs on O; three radial lone pairs on Cl",
"style": "clean textbook Lewis diagram, no text labels beyond element symbols"
}
},
{
"option": "d2",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CI₄",
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"style": "clean textbook Lewis diagram, no text labels beyond element symbols"
}
},
{
"option": "d3",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "NH₂Cl",
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"style": "clean textbook Lewis diagram, no text labels beyond element symbols"
}
}
]
}
Picture: Cl–C≡N drawn in a row — a single line Cl to C, triple lines C to N; three lone pairs on the Cl atom, one on the N atom. KEY
Picture: H–O–Cl drawn with the O in the middle; two lone pairs on the O atom, three on the Cl atom.
Picture: a central C with four single lines to I atoms; three lone pairs on each I atom.
Picture: a central N with single lines to two H atoms and one Cl atom; one lone pair on the N atom, three on the Cl atom.
A student writes that the H–H bond in hydrogen gas shares its electrons unequally, 'because the atom written first gets the bigger share.' Classify the sharing in H–H, with the correct reason.
Equal — the two atoms are the same element, so their electronegativities are identical. KEY
Unequal — the first atom in the formula holds the electrons more of the time.
Equal — hydrogen atoms are too small to pull on electrons at all.
Unequal — one hydrogen atom always turns into an ion inside the molecule.
Which single fact, on its own, guarantees that a molecule is nonpolar?
None of its bonds is polar. KEY
Its shape is a straight line.
It contains atoms of only two elements.
It contains no lone pairs on its central atom.
CMB-025 · medium · application · seq 5 · authored (wave-4; multiple-bond-counts-once rotation of pool 4's case, fresh instance C₂F₄) · numeric
The figure shows the Lewis diagram of C₂F₄. How many electron groups surround each C atom?
FIGURE (lewis-diagram · stimulus) — molecule: "C₂F₄" · structure: "C=C double lines in the middle; two single lines from each C to F atoms; three radial lone pairs on each F" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
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"figureShape": "stimulus",
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"figureType": "lewis-diagram",
"molecule": "C₂F₄",
"structure": "C=C double lines in the middle; two single lines from each C to F atoms; three radial lone pairs on each F",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 3 groups KEY
also accepted: 3 groups
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the double bond as two groups — a bond of any multiplicity counts once",
"feedback": null
},
{
"value": 6,
"misconception": "you counted the groups around both carbons — count at one atom at a time",
"feedback": null
},
{
"value": 2,
"misconception": "you skipped the double bond and counted only the C–F bonds",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the left carbon: two C–F single bonds and one C=C double bond = 3 groups. The double bond counts once, and the other carbon's bonds are its own. 3 + 0 = 3 electron groups."
}
The figure shows the Lewis diagram of AsBr₃. How many electron groups surround the As atom?
FIGURE (lewis-diagram · stimulus) — molecule: "AsBr₃" · structure: "As central; three single lines As–Br; one radial lone pair on As; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
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"molecule": "AsBr₃",
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"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 4 groups KEY
also accepted: 4 groups
wrongValueDiagnostics
[
{
"value": 3,
"misconception": "you skipped the lone pair on the As atom — a central-atom lone pair counts as one group",
"feedback": null
},
{
"value": 13,
"misconception": "you added the Br atoms' lone pairs — outer-atom lone pairs never count at the central atom",
"feedback": null
},
{
"value": 6,
"misconception": "you counted the bonding electrons instead of the groups",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the As atom: three As–Br single bonds = 3 groups. Lone pairs on the As atom: one = 1 group; the Br atoms' lone pairs are their own. 3 + 1 = 4 electron groups."
}
The figure shows the Lewis diagram of formyl fluoride, HFCO. Its central carbon has one bond to hydrogen, one bond to fluorine, and a double bond to oxygen. Classify the shape of the molecule.
FIGURE (lewis-diagram · stimulus) — molecule: "HFCO" · structure: "C central; single line C–H; single line C–F; double lines C=O; three radial lone pairs on F; two radial lone pairs on O" · style: "clean textbook Lewis diagram"raw spec
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"style": "clean textbook Lewis diagram"
}
}
Trigonal planar KEY
Linear
Not classifiable — the three outer atoms are all different elements
Not classifiable — the double bond must be counted as two groups, giving four
The Te atom of TeBr₂ has four electron groups, so a student classifies the molecule as tetrahedral. Why is the student wrong?
FIGURE (lewis-diagram · stimulus) — molecule: "TeBr₂" · structure: "Te central; single lines Te–Br to each side; two radial lone pairs on Te; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
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"figureShape": "stimulus",
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"figureType": "lewis-diagram",
"molecule": "TeBr₂",
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"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Tetrahedral requires all four groups to be bonding pairs — two of the Te atom's four are lone pairs, so it is not tetrahedral. KEY
The student's group count is wrong — lone pairs never count as electron groups, so the Te atom really has two.
The student miscounted the atoms — a tetrahedral molecule needs exactly four atoms, and TeBr₂ has only three.
Nothing is wrong — four electron groups always make a molecule tetrahedral.
A student sees four electron groups around the antimony in SbH₃ — three Sb–H bonds plus one lone pair, as the figure shows — and classifies the molecule as tetrahedral. What is the correct classification?
FIGURE (lewis-diagram · stimulus) — molecule: "SbH₃" · layout: "Sb central; three single bonds to H at left, right, and below; one lone pair on Sb pointing up" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
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"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Panels A to D each show the Lewis diagram of a molecule. Which panel shows a bent molecule?
FIGURE (lewis-panels · stimulus) — panels: [{"panel": "A", "description": "SeF₂ — Se central with single bonds to two F and two lone pairs on Se; three lone pairs on each F"}, {"panel": "B", "descript… · style: "clean textbook Lewis panels, boxes labeled A to D in one figure; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-panels",
"panels": [
{
"panel": "A",
"description": "SeF₂ — Se central with single bonds to two F and two lone pairs on Se; three lone pairs on each F"
},
{
"panel": "B",
"description": "SbF₃ — Sb central with single bonds to three F and one lone pair on Sb; three lone pairs on each F"
},
{
"panel": "C",
"description": "SnCl₄ — Sn central with single bonds to four Cl and no lone pair on Sn; three lone pairs on each Cl"
},
{
"panel": "D",
"description": "HBr — a single bond joins H to Br; three lone pairs on Br"
}
],
"style": "clean textbook Lewis panels, boxes labeled A to D in one figure; lone pairs radial with the two dots equidistant from the atom"
}
}
OF₂'s oxygen holds four electron groups, and the molecule is named bent — a name that reports only three atoms in a V. Which statement correctly accounts for the other two groups?
The other two groups are lone pairs — they occupy positions and push the two bonds together, but names report atom positions only. KEY
The other two groups merged into the two bonds, so only two groups remain.
The name is wrong, and OF₂ should be called tetrahedral to honor all four groups.
The other two groups sit so far from the oxygen that they count as electrons belonging to the fluorine atoms instead.
CMB-033 · medium · application · seq 12 · authored (wave-4; drawing-pick rotation, linear target with a multiplicity-convention foil, fresh instance ICN) · mcq4
The figure shows the Lewis diagram of ICN: a single bond joins I to C, a triple bond joins C to N, and the C atom holds no lone pair. Which drawing is the correct shape diagram of ICN?
FIGURE (lewis-diagram · stimulus) — molecule: "ICN" · structure: "I–C≡N in a row; single line I–C; triple lines C–N; three radial lone pairs on I; one radial lone pair on N" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
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"figureType": "lewis-diagram",
"molecule": "ICN",
"structure": "I–C≡N in a row; single line I–C; triple lines C–N; three radial lone pairs on I; one radial lone pair on N",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
},
"optionFigureSpecs": [
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}
},
{
"option": "d1",
"figureSpec": {
"figureType": "shape-diagram",
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}
},
{
"option": "d2",
"figureSpec": {
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},
{
"option": "d3",
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}
}
]
}
Drawing: I, C, and N along one straight line with plain single lines, name label 'linear' beneath. KEY
Drawing: the three atoms in a wide V with C at the point, name label 'bent' beneath.
Drawing: the three atoms in a straight line with the C-to-N connection drawn as three parallel lines, name label 'linear' beneath.
Drawing: C in the middle with I and N raised at matching angles above it, name label 'trigonal planar' beneath.
A student labels the H atom in H–I as δ− 'because it is the smaller atom.' In fact iodine is the stronger puller in this bond. Which labels are correct, and what rule decides?
I is δ−, H is δ+ — the labels follow electronegativity, not atom size. KEY
H is δ−, I is δ+ — the smaller atom always holds the electrons closer.
I is δ−, H is δ+ — because the heavier atom always takes the negative label.
Neither atom carries a partial charge, because the two atoms share equally.
OCS is linear like CO₂ — its central C atom makes one double bond to O and one to S — yet OCS is polar. Why do its two pulls fail to cancel?
The two pulls are unequal — the O end pulls harder than the S end — and only EQUAL pulls in opposite directions cancel. KEY
The two pulls point in the same direction rather than opposite directions, so they add instead of canceling.
Linear molecules cannot cancel pulls at all.
The S end carries a full negative charge that outweighs any cancellation.
CMB-034 · hard · transfer · seq 17 · authored (wave-4; formula-to-shape rotation, instance TeCl₂ — cross-form repeat with the freshened seq-19 form-A option, recorded; 'chlorine' is same-seq — the form-A demo carries it at seq 17) · mcq4
Starting from its formula, work out the shape of TeCl₂. Chlorine is a Group 17 element; tellurium is a Group 16 element.
Bent KEY
Linear
Tetrahedral
Trigonal pyramidal
CMB-032 · hard · transfer · seq 18 · seed:U5-G2.pool[26] (CMB-032 gateItems, James) - VERBATIM (field mapping only) · mcq4
Panels A to D each show the Lewis diagram of a molecule. Which panel shows a LINEAR molecule?
FIGURE (lewis-panels · stimulus) — panels: [{"panel": "A", "description": "SeCl₂ — Se central with single bonds to two Cl and two lone pairs on Se; three lone pairs on each Cl"}, {"panel": "B", "descr… · style: "clean textbook Lewis panels, boxes labeled A to D in one figure; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-panels",
"panels": [
{
"panel": "A",
"description": "SeCl₂ — Se central with single bonds to two Cl and two lone pairs on Se; three lone pairs on each Cl"
},
{
"panel": "B",
"description": "PI₃ — P central with single bonds to three I and one lone pair on P; three lone pairs on each I"
},
{
"panel": "C",
"description": "GeH₄ — Ge central with single bonds to four H and no lone pair on Ge"
},
{
"panel": "D",
"description": "CSe₂ — C central with double bonds to two Se, no lone pair on C; two lone pairs on each Se"
}
],
"style": "clean textbook Lewis panels, boxes labeled A to D in one figure; lone pairs radial with the two dots equidistant from the atom"
}
}
Panel D KEY
Panel A
Panel B
Panel C
CMB-041 · hard · transfer · seq 19 · authored (wave-4; nonpolar-pick rotation of the demo case, formula-pull phrasing; SbI₃/SeBr₂ are cross-form repeats (seq 1 E / seq 10 E), recorded — no same-form reuse) · mcq4
In each bond below, the pull on the shared electrons is toward the atom named second: Sn–Br (toward Br), N–F (toward F), H–S (toward S), H–I (toward I). Which of these molecules is nonpolar?
SnBr₄ (tetrahedral) KEY
NF₃ (trigonal pyramidal)
H₂S (bent)
HI
CMB-041 · hard · transfer · seq 20 · authored (wave-4; wrong-cancel rotation, instance SBr₂ — cross-form repeat with seq 2 form E, recorded; no same-form reuse) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
In SBr₂, each S–Br pull is toward the Br end, and the two pulls are identical. A student writes: 'The two identical pulls must cancel, so the molecule is nonpolar.' Which step went wrong, and what is the correct verdict?
The shape step was applied wrongly — SBr₂ is bent, so its two identical pulls sit at an angle and add up: polar. KEY
Nothing went wrong — two identical bonds always cancel each other, whatever the shape does.
The bond step — S and Br are the same kind of atom, so each bond is nonpolar.
The verdict is nonpolar, but only because the two lone pairs on the S atom absorb the bond pulls.
CMB-034 · medium · application · seq 21 · authored (wave-4; FRQ rotation, trigonal pyramidal target; instance PBr₃ — cross-form repeat with seq 9 form A, recorded (form C's seq 9 is the SbH₃ item, no same-form leak)) | stage-2 fix pass (_authoring_d): V-T12 typed-model fix · frq
Work out the shape of PBr₃ from its formula; the P atom is the central atom. Type your reasoning in three parts:
Work out the shape of PBr₃ from its formula; the P atom is the central atom. Type your reasoning in three parts:
(a) Total the valence electrons in the molecule, showing the arithmetic.
(b) Describe the completed Lewis diagram in words: what bonds the P atom makes, where the remaining electrons sit as lone pairs, and whether the P atom holds a lone pair.
(c) Name the molecule's shape, and justify the name from the routine's two counts.
Part a. Total the valence electrons in the molecule, showing the arithmetic.
Model: Total: 5 + 3 × 7 = 26 valence electrons.
Part b. Describe the completed Lewis diagram in words: what bonds the P atom makes, where the remaining electrons sit as lone pairs, and whether the P atom holds a lone pair.
Model: The P atom is central with three single P–Br bonds, using 6 electrons; 18 more complete the Br atoms' octets as three lone pairs each; the last 2 sit as one lone pair on the P atom.
Part c. Name the molecule's shape, and justify the name from the routine's two counts.
Model: Four electron groups with exactly one lone pair on the P atom — the molecule is trigonal pyramidal: the three Br atoms sit as a low tripod with the P atom above them.
Full model answer. (a) Total: 5 + 3 × 7 = 26 valence electrons.
(b) The P atom is central with three single P–Br bonds, using 6 electrons; 18 more complete the Br atoms' octets as three lone pairs each; the last 2 sit as one lone pair on the P atom.
(c) Four electron groups with exactly one lone pair on the P atom — the molecule is trigonal pyramidal: the three Br atoms sit as a low tripod with the P atom above them.
The germanium of GeF₄ holds four bonding pairs and no lone pairs. The four bonds spread to the corners of a tetrahedron instead of bunching on one side of the atom. What makes them spread?
FIGURE (lewis-diagram · stimulus) — molecule: "GeF₄" · structure: "Ge central; four single lines Ge–F; no lone pair on Ge; three radial lone pairs on each F" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
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"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "GeF₄",
"structure": "Ge central; four single lines Ge–F; no lone pair on Ge; three radial lone pairs on each F",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Electron groups repel each other, so they take up positions as far apart as possible around the central atom. KEY
The four F atoms attract one another, and that attraction holds the arrangement propped open.
The central atom's nucleus pushes the bonds apart.
The bonds simply keep whatever angles the flat Lewis diagram happens to show on the printed page.
The figure shows the Lewis diagram of ClCN: a single bond joins Cl to C, and a triple bond joins C to N. The C atom holds two electron groups and no lone pair. Which description of the molecule's shape is correct?
FIGURE (lewis-diagram · stimulus) — molecule: "ClCN" · structure: "Cl–C≡N in a row; single line Cl–C; triple lines C–N; three radial lone pairs on Cl; one radial lone pair on N" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "ClCN",
"structure": "Cl–C≡N in a row; single line Cl–C; triple lines C–N; three radial lone pairs on Cl; one radial lone pair on N",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
All three atoms lie in one straight line. KEY
The molecule bends at the carbon, because a triple bond outweighs a single bond.
The molecule makes a wide V, because the two outer atoms are different elements.
No single shape fits, because a triple bond cannot sit opposite a single bond.
CMB-035 · easy · recall · seq 3 · authored (wave-4; pick-the-equal-bond rotation of pool 33, fresh bond set, symbol-only naming) · mcq4
Four bonds are listed below; where the two elements differ, the stronger puller is named in parentheses. In which bond is the sharing of electrons equal?
Br–Br KEY
H–F (F)
N–O (O)
Si–Cl (Cl)
CMB-039 · easy · recall · seq 4 · authored (wave-4; two-factor fact rotation of pool 45, abstract — no instances) · mcq4
Which combination guarantees that a molecule is polar?
At least one polar bond AND a shape that does not cancel the bonds' pulls. KEY
Polar bonds alone — every molecule with polar bonds is polar.
A bent or pyramidal shape alone, whatever its bonds are like.
The figure shows the Lewis diagram of acetonitrile, CH₃CN. How many electron groups surround the C atom bonded to N?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃CN" · structure: "chain H₃C–C≡N; three single lines from the left C to H atoms and one single line to the right C; triple lines from the right C to N; one radial lone pair on… · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃CN",
"structure": "chain H₃C–C≡N; three single lines from the left C to H atoms and one single line to the right C; triple lines from the right C to N; one radial lone pair on N",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 2 groups KEY
also accepted: 2 groups
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the triple bond as three groups — a bond of any multiplicity counts once",
"feedback": null
},
{
"value": 6,
"misconception": "you counted the groups around both carbons — count at one atom at a time",
"feedback": null
},
{
"value": 3,
"misconception": "you added the N atom's lone pair — outer-atom lone pairs never count at the central atom",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at that carbon: one C–C single bond and one C≡N triple bond = 2 groups. A triple bond counts once, and the N atom's lone pair belongs to the N atom. 2 + 0 = 2 electron groups."
}
CMB-025 · medium · application · seq 6 · authored (wave-4; combined multiplicity-plus-lone-pair count, fresh instance NOCl; count item only — no shape asked, so the course's five-shape table is not touched) · numeric
The figure shows the Lewis diagram of NOCl: the N atom makes a double bond to the O atom and a single bond to the Cl atom, and holds one lone pair. How many electron groups surround the N atom?
FIGURE (lewis-diagram · stimulus) — molecule: "NOCl" · structure: "N central; double lines N=O on the left; single line N–Cl on the right; one radial lone pair on N; two radial lone pairs on O; three radial lone pairs on Cl" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "NOCl",
"structure": "N central; double lines N=O on the left; single line N–Cl on the right; one radial lone pair on N; two radial lone pairs on O; three radial lone pairs on Cl",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 3 groups KEY
also accepted: 3 groups
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the double bond as two groups — a bond of any multiplicity counts once",
"feedback": null
},
{
"value": 2,
"misconception": "you skipped the lone pair on the N atom — a central-atom lone pair counts as one group",
"feedback": null
},
{
"value": 8,
"misconception": "you added the outer atoms' lone pairs — they never count at the central atom",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the N atom: one N=O double bond (counts once) and one N–Cl single bond = 2 groups. Lone pairs on the N atom: one = 1 group. 2 + 1 = 3 electron groups."
}
CMB-027 · medium · application · seq 7 · authored (wave-4; planar classify rotation of pool 9's case, fresh instance H₂CSe) · mcq4
The figure shows the Lewis diagram of H₂CSe: the C atom makes one double bond to Se and single bonds to two H atoms. Classify the shape of the molecule.
FIGURE (lewis-diagram · stimulus) — molecule: "H₂CSe" · structure: "C central; double lines C=Se up; single lines to two H atoms below; no lone pair on C; two radial lone pairs on Se" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "H₂CSe",
"structure": "C central; double lines C=Se up; single lines to two H atoms below; no lone pair on C; two radial lone pairs on Se",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Trigonal planar KEY
Tetrahedral
Trigonal pyramidal
Bent
CMB-028 · medium · application · seq 8 · authored (wave-4; tetrahedral classify rotation of pool 13's case, fresh instance SiBr₄) · mcq4
The figure shows the Lewis diagram of SiBr₄. Classify the shape of the molecule.
FIGURE (lewis-diagram · stimulus) — molecule: "SiBr₄" · structure: "Si central; four single lines Si–Br; no lone pair on Si; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SiBr₄",
"structure": "Si central; four single lines Si–Br; no lone pair on Si; three radial lone pairs on each Br",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Tetrahedral KEY
Trigonal planar
Trigonal pyramidal
Bent
CMB-029 · medium · application · seq 9 · authored (wave-4; pyramidal classify rotation of pool 15's case, fresh instance SbF₃) · mcq4
The figure shows the Lewis diagram of SbF₃. Classify its shape.
FIGURE (lewis-diagram · stimulus) — molecule: "SbF₃" · structure: "Sb central; three single lines Sb–F; one radial lone pair on Sb; three radial lone pairs on each F" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SbF₃",
"structure": "Sb central; three single lines Sb–F; one radial lone pair on Sb; three radial lone pairs on each F",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Trigonal pyramidal KEY
Tetrahedral
Trigonal planar
Linear
CMB-030 · medium · application · seq 10 · authored (wave-4; bent classify rotation of pool 18's case, fresh instance TeF₂) · mcq4
The figure shows the Lewis diagram of TeF₂. Classify its shape.
FIGURE (lewis-diagram · stimulus) — molecule: "TeF₂" · structure: "Te central; single lines Te–F to each side; two radial lone pairs on Te; three radial lone pairs on each F" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "TeF₂",
"structure": "Te central; single lines Te–F to each side; two radial lone pairs on Te; three radial lone pairs on each F",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Bent KEY
Linear
Trigonal pyramidal
Tetrahedral
CMB-031 · medium · application · seq 11 · authored (wave-4; name-semantics rotation of pool 21's contrast, abstract — no instances) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
The central atom of a molecule holds four electron groups; exactly one of them is a lone pair. Which claim correctly connects the groups to the shape's NAME?
The name reports only the three atom positions — trigonal pyramidal — while the lone pair still occupies the fourth position. KEY
The name must report all four positions, so the molecule is called tetrahedral.
The lone pair is dropped from the name because it stops repelling the other groups once the shape has formed.
The name is trigonal planar, because the three attached atoms flatten out once the lone pair is ignored.
The figure shows the Lewis diagram of CH₃Br: the carbon makes single bonds to three H atoms and one Br atom, with no lone pair. Which drawing is the correct shape diagram of CH₃Br?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃Br" · structure: "C central; single lines to three H and one Br; no lone pair on C; three radial lone pairs on Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃Br",
"structure": "C central; single lines to three H and one Br; no lone pair on C; three radial lone pairs on Br",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
},
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "CH₃Br",
"layout": "C central; Br above it; three H spread as a low tripod below; plain bond lines; name label 'tetrahedral' beneath",
"style": "clean textbook shape diagram"
}
},
{
"option": "d1",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "CH₃Br",
"layout": "C at the center of a flat square, the Br and three H at the square's corners, name label 'tetrahedral' beneath",
"style": "clean textbook shape diagram"
}
},
{
"option": "d2",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "CH₃Br",
"layout": "C above three H drawn as a low tripod, no Br anywhere, name label 'trigonal pyramidal' beneath",
"style": "clean textbook shape diagram"
}
},
{
"option": "d3",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "CH₃Br",
"layout": "C with Br and three H around it plus a fifth small empty circle, name label 'tetrahedral' beneath",
"style": "clean textbook shape diagram"
}
}
]
}
Drawing: C at the center, its four atoms at a tetrahedron's corners — Br above, three H as a low tripod — plain lines, name label 'tetrahedral' beneath. KEY
Drawing: C at the center of a flat square with the four atoms at its corners, name label 'tetrahedral' beneath.
Drawing: C above the three H drawn as a tripod with the Br left out, name label 'trigonal pyramidal' beneath.
Drawing: C with the four attached atoms and a fifth small circle drawn where a lone pair would sit, name label 'tetrahedral' beneath.
CMB-036 · medium · application · seq 13 · authored (wave-4; near-equal-pulls rotation of pool 38's case, fresh pair H–P; 'hydrogen' is same-seq — pool 38 already carries it at seq 13) · mcq4
Hydrogen and phosphorus pull shared electrons with almost the same strength, and both are nonmetals. Classify the H–P bond.
A nonpolar covalent bond KEY
A polar covalent bond
An ionic bond
A metallic bond
CMB-037 · medium · application · seq 14 · authored (wave-4; label rotation of pool 39's case, fresh pair H–S; 'sulfur'/'hydrogen' are same-seq — pools 39/41 already carry them at seq 14) · mcq4
In the H–S bond, the S atom pulls the shared electrons harder. Which δ labels are correct?
S is δ−, H is δ+ KEY
H is δ−, S is δ+
Both ends are neutral, because the atoms stay bonded.
S is −1, H is +1
CMB-038 · medium · application · seq 15 · authored (wave-4; why-δ+ rotation of pool 43's case, fresh pair Se–F; 'fluorine' is same-seq — pool 44 already carries it at seq 15) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
Fluorine pulls shared electrons more strongly than selenium. Why does the SELENIUM end of the Se–F bond go δ+?
Because the F atom draws the shared electrons closer, leaving the Se end holding a smaller share of the negative charge. KEY
Because the Se atom hands one of its electrons over to the F atom completely, just the way an ion would.
Because the selenium end gains extra protons once the bond forms.
Because larger atoms are always δ+ in any bond.
CMB-040 · medium · application · seq 16 · authored (wave-4; symmetric-cancel rotation of pool 48's case, fresh instance SiI₄, formula-pull phrasing) · mcq4
SiI₄ is tetrahedral, and each of its four Si–I bonds is polar, with the pull toward the I end. A student decides the molecule must be polar. What is the correct verdict, and why?
Nonpolar — equal pulls in opposite directions cancel, leaving no overall pull. KEY
Polar — four polar bonds cannot all cancel.
Polar — pulls can only cancel in flat molecules.
Nonpolar — but only because Si–I bonds are too weak to pull at all.
CMB-034 · hard · transfer · seq 17 · re-instanced 2026-10-13 (A1 forms pass; James ruling 2026-10-08 #19): NF₃ was CMB-029 WE2's instance word for word -> BiCl₃ (bismuth(III) chloride, a real trigonal-pyramidal molecule; Group 15 central atom like the SbCl₃ gate item at A#17; the unfamiliar central atom's valence count is supplied in words — the gate's ADJ-2-style worded-number register — rather than as Group 15/17 digits, which the numeric scan treats as instances); same skill (formula -> Lewis routine -> shape), same electron total (26), same misconception set; bismuth appears nowhere else in Unit 5 (forms or specs). Previous source: authored (wave-4; formula-to-shape rotation, instance NF₃ — CMB-029-WE corpus, other-lesson WARN). · mcq4
Starting from its formula, work out the shape of BiCl₃. Bismuth has five valence electrons, and each Cl atom has seven.
Trigonal pyramidal KEY
Trigonal planar
Tetrahedral
Linear
CMB-032 · hard · transfer · seq 18 · authored (wave-4; any-shape routine rotation, fresh instance SnH₄) · mcq4
The figure shows the Lewis diagram of SnH₄: the Sn atom makes single bonds to four H atoms and holds no lone pair. Run the two-count routine and classify the shape.
FIGURE (lewis-diagram · stimulus) — molecule: "SnH₄" · structure: "Sn central; four single lines Sn–H; no lone pairs anywhere" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SnH₄",
"structure": "Sn central; four single lines Sn–H; no lone pairs anywhere",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Tetrahedral KEY
Trigonal pyramidal
Bent
Trigonal planar
CMB-041 · hard · transfer · seq 19 · authored (wave-4; polar-pick rotation, fresh instance CH₃I; C₂H₆/SnBr₄ same-seq reuses (A5), CSe₂ cross-form repeat with seq 18, recorded) · mcq4
In each bond below, the pull on the shared electrons is toward the atom named second; a C–H bond has almost no pull either way: C–I (toward I), Sn–Br (toward Br), C–Se (toward Se). Which of these molecules is polar?
CH₃I (tetrahedral) KEY
SnBr₄ (tetrahedral)
C₂H₆ (a tetrahedron at each carbon)
CSe₂ (linear)
CMB-041 · hard · transfer · seq 20 · authored (wave-4; pyramid-cancel critique rotation, instance AsI₃ — cross-form repeat with seq 9 form E, recorded; no same-form reuse) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
In AsI₃, the pull of each As–I bond is toward the I end, and the three pulls are identical. A student classifies this trigonal pyramidal molecule as nonpolar 'because three identical pulls must cancel.' What did the student get wrong?
The shape step — a pyramid angles its three pulls toward one side, so they add up instead of canceling: AsI₃ is polar. KEY
Nothing — three identical pulls always cancel.
The bond step — As–I bonds cannot be polar because both atoms are large.
The verdict is right but the reason is wrong: it is the lone pair, not the bonds, that cancels the three pulls.
CMB-034 · medium · application · seq 21 · authored (wave-4; FRQ rotation, bent target; instance SCl₂ — cross-form repeat with the seq 6 form-A numeric seed, recorded (form D's seq 6 is the NOCl item, no same-form leak); SCl₂ is a CMB-030 WE instance, other-lesson WARN documented) | stage-2 fix pass (_authoring_d): V-T12 typed-model fix · frq
Work out the shape of SCl₂ from its formula; the S atom is the central atom. Type your reasoning in three parts:
Work out the shape of SCl₂ from its formula; the S atom is the central atom. Type your reasoning in three parts:
(a) Total the valence electrons in the molecule, showing the arithmetic.
(b) Describe the completed Lewis diagram in words: what bonds the S atom makes, where the remaining electrons sit as lone pairs, and whether the S atom holds lone pairs.
(c) Name the molecule's shape, and justify the name from the routine's two counts.
Part a. Total the valence electrons in the molecule, showing the arithmetic.
Model: Total: 6 + 2 × 7 = 20 valence electrons.
Part b. Describe the completed Lewis diagram in words: what bonds the S atom makes, where the remaining electrons sit as lone pairs, and whether the S atom holds lone pairs.
Model: The S atom is central with two single S–Cl bonds, using 4 electrons; 12 more complete the Cl atoms' octets as three lone pairs each; the last 4 sit as two lone pairs on the S atom.
Part c. Name the molecule's shape, and justify the name from the routine's two counts.
Model: Four electron groups with exactly two lone pairs on the S atom — only two positions hold atoms, so the three atoms make a wide open V: the molecule is bent.
Full model answer. (a) Total: 6 + 2 × 7 = 20 valence electrons.
(b) The S atom is central with two single S–Cl bonds, using 4 electrons; 12 more complete the Cl atoms' octets as three lone pairs each; the last 4 sit as two lone pairs on the S atom.
(c) Four electron groups with exactly two lone pairs on the S atom — only two positions hold atoms, so the three atoms make a wide open V: the molecule is bent.
The antimony of SbI₃ holds three bonding pairs and one lone pair. When the groups spread out around the antimony, which of them take part in the spreading?
FIGURE (lewis-diagram · stimulus) — molecule: "SbI₃" · structure: "Sb central; three single lines Sb–I; one radial lone pair on Sb; three radial lone pairs on each I" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SbI₃",
"structure": "Sb central; three single lines Sb–I; one radial lone pair on Sb; three radial lone pairs on each I",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
All four groups — the lone pair is an electron group too, so it repels the others and claims its own position. KEY
Only the three bonds — a lone pair carries no electric charge of its own, so nothing ever repels it.
Only the lone pair moves — the bonds are locked in place by their atoms.
None of them — the groups stay wherever the Lewis diagram happens to draw them.
CMB-026 · easy · recall · seq 2 · authored (wave-4; two-atoms-is-not-enough critique rotation of pool 7's case, fresh instance SBr₂; 'sulfur' reused same-seq only — pool 7's key already carries it at seq 2) · mcq4
Only two atoms are attached to the S atom of SBr₂, and a student concludes that the three atoms must lie in a straight line. Why is the conclusion wrong?
FIGURE (lewis-diagram · stimulus) — molecule: "SBr₂" · structure: "S central; single lines S–Br to each side; two radial lone pairs on S; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SBr₂",
"structure": "S central; single lines S–Br to each side; two radial lone pairs on S; three radial lone pairs on each Br",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
The S atom's two lone pairs are electron groups too — four groups with two attached atoms keep the three atoms out of a straight line. KEY
Nothing is wrong — a molecule with exactly two attached atoms is always linear.
The molecule is linear, but only because the two outer atoms are too large to bend inward.
The student is right about the straight line but wrong about the reason: the lone pairs force the atoms straight.
CMB-035 · easy · recall · seq 3 · authored (wave-4; slight-difference classify rotation of pool 34, fresh pair I–Cl; 'chlorine'/'iodine' words are same-seq — pools 33/34 already carry them at seq 3) · mcq4
In the I–Cl bond, the Cl atom pulls the shared electrons a little more strongly than the I atom. Classify the sharing, with the correct reason.
Unequal — any difference in electronegativity makes the pulls uneven. KEY
Equal — the two atoms are both halogens, and same-family atoms share equally.
Equal — a small difference is too small to matter.
Unequal — but the electrons shift toward the iodine, because it is the larger atom.
CMB-039 · easy · recall · seq 4 · authored (wave-4; fact-read rotation of pool 46, abstract — no instances) · mcq4
Two facts are reported about a molecule: every one of its bonds is polar, and its shape does NOT cancel the bonds' pulls. What follows?
The molecule is polar — it has a slightly positive end and a slightly negative end. KEY
The molecule is nonpolar — bond pulls always cancel somewhere.
Nothing follows until the number of atoms is known.
The molecule is polar only if it also has a lone pair on its central atom.
The figure shows the Lewis diagram of propyne, CH₃–C≡CH. How many electron groups surround the middle carbon?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃–C≡CH" · structure: "chain H₃C–C≡C–H; three single lines from the left C to H atoms; single line to the middle C; triple lines from the middle C to the right C; single line from… · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃–C≡CH",
"structure": "chain H₃C–C≡C–H; three single lines from the left C to H atoms; single line to the middle C; triple lines from the middle C to the right C; single line from the right C to its H; no lone pairs",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 2 groups KEY
also accepted: 2 groups
wrongValueDiagnostics
[
{
"value": 4,
"misconception": "you counted the triple bond as three groups — a bond of any multiplicity counts once",
"feedback": null
},
{
"value": 8,
"misconception": "you counted the shared electrons around the middle carbon instead of the groups",
"feedback": null
},
{
"value": 3,
"misconception": "you gave the middle carbon a lone pair it does not have",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the middle carbon: one single bond to the CH₃ carbon and one triple bond to the CH carbon = 2 groups. A triple bond counts once. 2 + 0 = 2 electron groups."
}
The figure shows the Lewis diagram of CH₃OH. How many electron groups surround the O atom?
FIGURE (lewis-diagram · stimulus) — molecule: "CH₃OH" · structure: "chain H₃C–O–H; three single lines from C to H atoms; single line C–O; single line O–H; two radial lone pairs on O" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CH₃OH",
"structure": "chain H₃C–O–H; three single lines from C to H atoms; single line C–O; single line O–H; two radial lone pairs on O",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Answer: 4 groups KEY
also accepted: 4 groups
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted only the bonds — the two lone pairs on the O atom each count as one group",
"feedback": null
},
{
"value": 8,
"misconception": "you counted electrons around the O atom instead of groups",
"feedback": null
},
{
"value": 3,
"misconception": "you counted only one of the O atom's two lone pairs",
"feedback": null
}
]
feedback
{
"keyExplanation": "Bonds at the O atom: one O–C single bond and one O–H single bond = 2 groups. Lone pairs on the O atom: two = 2 groups. 2 + 2 = 4 electron groups."
}
CMB-027 · medium · application · seq 7 · authored (wave-4; per-carbon planar read rotation of pool 11's mixed-partner case, fresh instance C₂Cl₄) · mcq4
The figure shows the Lewis diagram of C₂Cl₄: the two carbons share a double bond, and each carbon also makes single bonds to two Cl atoms. What is the shape at EACH carbon?
FIGURE (lewis-diagram · stimulus) — molecule: "C₂Cl₄" · structure: "C=C double lines in the middle; two single lines from each C to Cl atoms; three radial lone pairs on each Cl" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₂Cl₄",
"structure": "C=C double lines in the middle; two single lines from each C to Cl atoms; three radial lone pairs on each Cl",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Trigonal planar — each carbon holds three groups and no lone pair. KEY
Tetrahedral — each carbon holds four groups.
Linear — the C=C bond makes the whole molecule one straight chain.
The figure shows the Lewis diagram of CHF₂Cl: the central C atom bonds one H, two F, and one Cl, with no lone pair. Classify the shape of the molecule.
FIGURE (lewis-diagram · stimulus) — molecule: "CHF₂Cl" · structure: "C central; single lines to one H, two F, and one Cl; no lone pair on C; three radial lone pairs on each halogen" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "CHF₂Cl",
"structure": "C central; single lines to one H, two F, and one Cl; no lone pair on C; three radial lone pairs on each halogen",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Tetrahedral KEY
Trigonal pyramidal
Trigonal planar
It has no single shape, because the outer atoms are of three different kinds.
CMB-029 · medium · application · seq 9 · authored (wave-4; four-groups-but-pyramid rotation of pool 17's case, fresh instance AsI₃) · mcq4
A student sees four electron groups around the As atom in AsI₃ — three As–I bonds plus one lone pair — and classifies the molecule as tetrahedral. What is the correct classification?
FIGURE (lewis-diagram · stimulus) — molecule: "AsI₃" · structure: "As central; three single lines As–I; one radial lone pair on As; three radial lone pairs on each I" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "AsI₃",
"structure": "As central; three single lines As–I; one radial lone pair on As; three radial lone pairs on each I",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Trigonal pyramidal — only the three positions holding atoms appear in the name. KEY
Tetrahedral — four groups always means tetrahedral.
Trigonal planar — three attached atoms make a flat triangle.
Only two Br atoms are attached to the Se atom of SeBr₂, so a student writes that the three atoms must lie in a straight line. What is the correct classification, and why?
FIGURE (lewis-diagram · stimulus) — molecule: "SeBr₂" · structure: "Se central; single lines Se–Br to each side; two radial lone pairs on Se; three radial lone pairs on each Br" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "SeBr₂",
"structure": "Se central; single lines Se–Br to each side; two radial lone pairs on Se; three radial lone pairs on each Br",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Bent — the Se atom's two lone pairs claim positions too, forcing the two bonds into a wide open V. KEY
Linear — two attached atoms always line up straight.
Trigonal pyramidal — the two lone pairs stack together on one side like the leg of a tripod.
Tetrahedral — four groups means four corners.
CMB-031 · medium · application · seq 11 · authored (wave-4; two-molecule name contrast, abstract — no instances) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
Two molecules both have central atoms with four electron groups. In the first, all four groups hold atoms; in the second, two of the groups are lone pairs. What do the shape names report?
The first is tetrahedral, the second bent — names report only where atoms sit, though all four groups hold positions in both. KEY
Both molecules are tetrahedral, because both of their central atoms hold four spread-out electron groups.
The second has no shape name, because lone pairs make a shape unnameable.
The first is bent and the second is tetrahedral.
CMB-033 · medium · application · seq 12 · authored (wave-4; drawing-pick rotation, planar target with a multiplicity foil, instance C₂H₄ — cross-form repeat with seq 5 form B, recorded) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
The figure shows the Lewis diagram of C₂H₄: the two carbons share a double bond, and each carbon also bonds two H atoms; neither carbon holds a lone pair. Which drawing is the correct shape diagram of C₂H₄?
FIGURE (lewis-diagram · stimulus) — molecule: "C₂H₄" · structure: "C=C double lines in the middle; two single lines from each C to H atoms; no lone pairs" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "C₂H₄",
"structure": "C=C double lines in the middle; two single lines from each C to H atoms; no lone pairs",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
},
"optionFigureSpecs": [
{
"option": "key",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "C₂H₄",
"layout": "six atoms flat on the page: the two C joined by one plain line, each C with its two H spread to make a shallow triangle; name label 'trigonal planar at each carbon' beneath",
"style": "clean textbook shape diagram"
}
},
{
"option": "d1",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "C₂H₄",
"layout": "six atoms flat on the page with the C-to-C connection drawn as two parallel lines; name label 'trigonal planar at each carbon' beneath",
"style": "clean textbook shape diagram"
}
},
{
"option": "d2",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "C₂H₄",
"layout": "two C drawn with H atoms tilted up out of the page like tent flaps; name label 'tetrahedral' beneath",
"style": "clean textbook shape diagram"
}
},
{
"option": "d3",
"figureSpec": {
"figureType": "shape-diagram",
"molecule": "C₂H₄",
"layout": "C, C, and the four H all drawn along one straight row; name label 'linear' beneath",
"style": "clean textbook shape diagram"
}
}
]
}
Drawing: all six atoms flat on the page — each C at the center of a shallow triangle made of its two H and the other C — plain single lines, name label 'trigonal planar at each carbon' beneath. KEY
Drawing: exactly the same six-atom flat arrangement, but with the C-to-C connection drawn as two parallel lines instead of one, name label 'trigonal planar at each carbon' beneath.
Drawing: the two C with their H atoms folded up out of the page like a tent, name label 'tetrahedral' beneath.
Drawing: all six atoms in one straight row, name label 'linear' beneath.
CMB-036 · medium · application · seq 13 · authored (wave-4; ionic-band rotation of pool 36's case, fresh pair Mg–O; 'oxygen' is same-seq — pool 37 already carries it at seq 13) · mcq4
Magnesium is a metal and oxygen is a nonmetal, and their electronegativity difference is very large. Classify the bond in MgO.
An ionic bond KEY
A polar covalent bond
A nonpolar covalent bond
A metallic bond
CMB-037 · medium · application · seq 14 · authored (wave-4; label rotation, fresh pair Ge–O; 'oxygen' is same-seq — pool 39 already carries it at seq 14; germanium is lexicon-unlisted) · mcq4
In the Ge–O bond, the O atom pulls the shared electrons harder than the Ge atom. Which labels are correct?
O is δ−, Ge is δ+ KEY
Ge is δ−, O is δ+
Both atoms are δ−, since both pull on the shared electrons.
In the Si–F bond, the F atom pulls the shared electrons much more strongly than the Si atom. A student reads the δ− label on the fluorine end and says the fluorine 'has taken the shared electrons completely.' What has actually happened?
The fluorine only holds the shared electrons CLOSER — they still belong to the bond, so the charge stays partial. KEY
The fluorine has taken both of the shared electrons for itself, and δ− marks its full −1 ion charge.
The electrons sit exactly midway; δ− is just a naming custom.
The silicon end has also gained electrons, balancing the fluorine's gain.
CMB-040 · medium · application · seq 16 · authored (wave-4; broken-identity rotation of pool 49's case, fresh instances GeBr₄/GeHBr₃) | stage-2 fix pass (_authoring_d): V-T4 length balance · mcq4
GeBr₄ is nonpolar, but swap one Br for an H to make GeHBr₃ and the molecule becomes polar. Why does the swap stop the cancellation?
The four pulls are no longer identical — a Ge–H pull differs from a Ge–Br pull, so they no longer balance. KEY
The shape changes from tetrahedral to trigonal planar when the H arrives.
The H atom always adds a lone pair to the central atom.
The molecule becomes polar simply because it now contains atoms of three different elements.
Starting from its formula, work out the shape of C₂N₂. The two carbons sit in the middle, bonded to each other, and each carbon also bonds one N atom. What is the shape at EACH carbon — and so of the whole molecule?
Linear — each carbon has just two groups (one C–C bond and one C≡N bond), so all four atoms lie in one straight line. KEY
Bent at each carbon, because the multiple bonds crowd the middle of the molecule.
Trigonal planar at each carbon — the triple bond spreads out to count as two of its three groups.
Tetrahedral at each carbon.
CMB-032 · hard · transfer · seq 18 · authored (wave-4; any-shape routine rotation, instance PI₃ — same-seq reuse of pool 26's panel B, A5 class) · mcq4
The figure shows the Lewis diagram of PI₃: the P atom makes single bonds to three I atoms and holds one lone pair. Run the two-count routine and classify the shape.
FIGURE (lewis-diagram · stimulus) — molecule: "PI₃" · structure: "P central; three single lines P–I; one radial lone pair on P; three radial lone pairs on each I" · style: "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "lewis-diagram",
"molecule": "PI₃",
"structure": "P central; three single lines P–I; one radial lone pair on P; three radial lone pairs on each I",
"style": "clean textbook Lewis diagram; lone pairs radial with the two dots equidistant from the atom"
}
}
Trigonal pyramidal KEY
Tetrahedral
Trigonal planar
Linear
CMB-041 · hard · transfer · seq 19 · authored (wave-4; nonpolar-pick rotation, formula-pull phrasing; GeI₄/SbBr₃/TeF₂ are cross-form repeats (seq 9 B panel / seq 7 B / seq 10 D), recorded — no same-form reuse; HF fresh) · mcq4
In each bond below, the pull on the shared electrons is toward the atom named second: Ge–I (toward I), Sb–Br (toward Br), Te–F (toward F), H–F (toward F). Which of these molecules is nonpolar?
In H–Br, the Br end clearly out-pulls the H end for the shared electrons, so the bond is polar — δ+ on the H end, δ− on the Br end. A student nevertheless classifies the molecule as nonpolar 'because one small pull cannot count for a whole molecule.' What is the correct verdict?
Polar — a two-atom molecule has nothing to cancel its single pull, however small the pull is. KEY
Nonpolar — small differences round to zero.
Nonpolar — a molecule made of just two atoms always counts as symmetric.
Work out the shape of CH₂Br₂ from its formula; the central atom is C. Type your reasoning in three parts:
Work out the shape of CH₂Br₂ from its formula; the central atom is C. Type your reasoning in three parts:
(a) Total the valence electrons in the molecule, showing the arithmetic. (An H atom brings one valence electron.)
(b) In words, describe the finished Lewis diagram: which bonds the C atom forms, where any leftover electrons sit as lone pairs, and whether the C atom carries a lone pair.
(c) Name the molecule's shape, and justify the name from the routine's two counts.
Part a. Total the valence electrons in the molecule, showing the arithmetic. (An H atom brings one valence electron.)
Part b. In words, describe the finished Lewis diagram: which bonds the C atom forms, where any leftover electrons sit as lone pairs, and whether the C atom carries a lone pair.
Model: The carbon is central with two C–H and two C–Br single bonds, using 8 electrons; the remaining 12 sit as three lone pairs on each Br atom; the H atoms take no lone pairs and the carbon holds none.
Part c. Name the molecule's shape, and justify the name from the routine's two counts.
Model: Four electron groups with no lone pair on the carbon — the molecule is tetrahedral. Two kinds of outer atom do not change the four-group, no-lone-pair count.
Full model answer. (a) Total: 4 + 2 × 1 + 2 × 7 = 20 valence electrons.
(b) The carbon is central with two C–H and two C–Br single bonds, using 8 electrons; the remaining 12 sit as three lone pairs on each Br atom; the H atoms take no lone pairs and the carbon holds none.
(c) Four electron groups with no lone pair on the carbon — the molecule is tetrahedral. Two kinds of outer atom do not change the four-group, no-lone-pair count.
End of Topic Test: Forces between molecules & The three intermolecular forces & Forces and properties (u05-t3 · 5 forms × 21 items · 105 total)
David's notes for James:
STRUCTURAL ADJUDICATION F1 'hbond-force-name' (confirm): this gate's topics ARE the three intermolecular forces, and the taught NAME of the strongest one embeds the MATERIALS token 'hydrogen' - so V-T7's substance-exclusivity scans are structurally unsatisfiable for the CMB-051..060 rows (every item of the block must name the force). Everything text-fixable WAS content-fixed first (955 baseline violations -> 207+14 patch ops): after the waves, the word 'hydrogen' survives ONLY inside 'hydrogen bond(s)/bonding', verified per token - the gate-local validate_with_adjudications.py wrapper (U3-G2 precedent, run over the UNTOUCHED shared validator) re-derives every excused slot's scanned token stream and refuses the excusal if any 'hydrogen' is not immediately followed by bond/bonds/bonding (the check genuinely fired mid-QC and poisoned a slot until D#13 was fixed). NEW excused kind vs the U3-G2 wrapper and this gate's principal judgment call: WITHIN-FORM ADJACENCY, F1-only - the CMB-051/052/053 block sits at consecutive seqs on every form and each of those items must name the force, so the force name telegraphs nothing. Flag if you want the block dispersed instead.
STRUCTURAL ADJUDICATION F3 'cmb058-water-anomaly' (confirm): CMB-058's taught object IS water + 100 C, so the five seq-19 slots keep water and rotate FENCE PARTNERS around it (CO / ethane / relevance / methane / bond-breaking facets); the partner constants -162 C (methane, the rule-line pair itself) and -89 C (ethane, your pool[49] verbatim) are physical constants from the taught pairs. Tokens {100, 162, 89} + 'water' are excused ONLY at seq 19 (slot-restricted); water everywhere else in the bank was content-removed (A#17 freshened).
SYMBOL/FORMULA POLICY (recorded adjudication - confirm the convention): element-NAME tokens whose referent is an ATOM inside a case molecule (the H-on-N/O/F checklist vocabulary) are written in course-canonical notation in scanned fields - N-H/O-H/C-H groups, 'the O atom', formulas (CO2, H2O2, NF3, ...; exported as Unicode subscripts). This is a content alignment (the course itself writes O-H/N-H/C-H), not a scanner dodge: wherever a substance NAME is the instance, the name stays and the scan sees it at its single ledger slot.
Seed census: ALL 57 pool seeds placed (form A 20 / B 19 / C 18 - your curation depth; forms D/E fully authored; 0 spares). Your 6 demo_curated items are POOL DUPLICATES (demo 0-5 = pool 33/34/35/51/52/53, stem-verified) - placed once each at seqs 12/13/18 with both refs cited. prod_seeds is EMPTY, so the FRQ is authored (next note). 23 of the 57 seeds carried a must_freshen_instance flag from the stage-1 freshness scan; SEED RULING freshenings to confirm: A#17's seed table was CMB-057's own student-seen check trio (H2O/H2S/O2) -> formic acid 101 / bromomethane 4 / ethene -104 C (real bps, fresh substances); A#15's ethanol/dimethyl-ether pair is CMB-051-spec-visible -> propan-2-ol / ethyl methyl ether (83 / 7 C, real); A#18's NaF -> strontium chloride 874 C (first swap LiF was itself CMB-059's WE example, caught by the gram scan). Structures, keys, and misconception classes verbatim throughout.
Zero NOTA/AOTA this gate: none of the 57 seeds carries a None/All-of-the-above seat, so the opportunistic replacement rule (ANSWERS #2) never fired. (The U5 CMB-028 keyed-NOTA v2-spec fix was verified not applicable at seed placement - CMB-028 is not in this gate's scope.)
FRQ design (confirm): seq 21 = authored unlabeled-solids classification on capstone CMB-059 (TEKS-CHEM-7D; your spec extraNotes names it the U5-G3 capstone): three crystalline solids, measured melting points in a rendered table -> (a) classify X and Y naming what melting must overcome in each (40), (b) correct the 'low melting point proves weak covalent bonds' claim (30), (c) classify Z from its melting point (30); rubric sums 100, parts split losslessly. Round-1 blind caught the five forms sharing near-identical FRQ stems - each form now has its own framing and solid labels (A X/Y/Z storeroom, B P/Q/R prep-room, C J/K/L stockroom, D F/G/H lab-bench tray, E R/S/T supply cupboard) renamed through parts, model answers, rubrics, and figure rows. Standing typed-plan flag applies.
Blind-round content fixes worth your eyes: (1) the round's one hard fail - a seq-12 checklist item whose subset options were rated defensible - was CLASS-SWEPT: all five seq-12 stems now demand the complete set ('Which choice lists ALL of the intermolecular forces acting between ...'); (2) B#18's key was verbatim-identical to its own form's FRQ part-(b) model answer -> rewritten to an ion-pairing-vs-lattice claim critique; C#18 rehearsed its FRQ's task -> rewritten to a named-substance contrast (vanillin 81 C / rubidium chloride 715 C); (3) B#15 had two options selecting the same substance (bare pick + pick-with-rationale, inherited from your seed's acetone-double pattern) -> one replaced with the similar-size dead-end misconception.
sol (authoritative cross-vendor QC) converged 12 -> 1 -> 0 -> 0 fails over 4 loops with ZERO overrides carried; rulings folded into content include: 'only dipole-dipole' phrasings corrected to 'strongest attraction is dipole-dipole' (the additive rule - dispersion acts between ALL molecules); the dispersion-size trend scoped to 'two similar substances' (CMB-048's like-with-like caveat); two TRUE-but-irrelevant distractors replaced with false-inference distractors (B#17, C#19); D#11's geometry distractor now names formic acid so it is judgeable. ONE checkable-fact dispute to flag: sol holds GeCl4's boiling point at ~83 C vs our 86-86.5 C sources (literature genuinely splits) - D#15's explanation now states the uncontested QUALITATIVE contrast (GeH4 boils at -88 C; GeCl4 is liquid well above room temperature) instead of quoting a disputed number. Flag if you hold a canonical GeCl4 value.
Recorded advisory classes (blind reviewers, not content-fixed - spec-design authority): mechanism keys quote the taught MECH-* sentences VERBATIM by spec mandate, so they draw longest-option/definition-echo flags (V-T4, the recorded hard bar, passes on all 105 items - shortening keys would break the verbatim-mechanism requirement); the seq 1->20 easy->hard ladder inside one topic places rule-statement items before rule-application items (cross-item-cueing flags; the two WORST instances - the FRQ echoes above - were content-fixed); B#20/D#15-class stems SUPPLY the force comparison (CMB-055 EXTRA mandates supplied comparisons; the tested link is forces -> boiling point).
gate_config ledger (all recorded, _shared untouched): 2 adjudicated_instance_families (notes 1-2 above) + 3 extra_task_idioms ('the claim is wrong because/only', 'the student is right' - option-side verdict openers of your claim-critique family, which the automatic idiom derivation does not harvest from option text). Instance hygiene: the fresh-instance set is classroom-safe throughout; zero uranium/plutonium/radium/actinide/enrichment/reactor/weapon/radiation framings bank-wide (re-swept at packaging, 0 hits). Documented-for-maintainer _shared candidates (READ-ONLY this wave, not applied): the molecule-pair blind-figure family (rendered by a gate-local augmenter, U2/U3 precedent) and the A7 force-name relief key that would retire these per-gate wrappers.
FRQ delivery: your `prod` draw-on-paper class is delivered as a typed diagram-PLAN task (state kinds/recipes/counts/spacing; rubric grades the same observables). Confirm this mapping (pending from the U01-G1 round-trip).
full notes file
# u05-t3 — notes/queries from David's side (U5-G3)
1. STRUCTURAL ADJUDICATION F1 'hbond-force-name' (confirm): this gate's topics ARE the three intermolecular forces, and the taught NAME of the strongest one embeds the MATERIALS token 'hydrogen' - so V-T7's substance-exclusivity scans are structurally unsatisfiable for the CMB-051..060 rows (every item of the block must name the force). Everything text-fixable WAS content-fixed first (955 baseline violations -> 207+14 patch ops): after the waves, the word 'hydrogen' survives ONLY inside 'hydrogen bond(s)/bonding', verified per token - the gate-local validate_with_adjudications.py wrapper (U3-G2 precedent, run over the UNTOUCHED shared validator) re-derives every excused slot's scanned token stream and refuses the excusal if any 'hydrogen' is not immediately followed by bond/bonds/bonding (the check genuinely fired mid-QC and poisoned a slot until D#13 was fixed). NEW excused kind vs the U3-G2 wrapper and this gate's principal judgment call: WITHIN-FORM ADJACENCY, F1-only - the CMB-051/052/053 block sits at consecutive seqs on every form and each of those items must name the force, so the force name telegraphs nothing. Flag if you want the block dispersed instead.
2. STRUCTURAL ADJUDICATION F3 'cmb058-water-anomaly' (confirm): CMB-058's taught object IS water + 100 C, so the five seq-19 slots keep water and rotate FENCE PARTNERS around it (CO / ethane / relevance / methane / bond-breaking facets); the partner constants -162 C (methane, the rule-line pair itself) and -89 C (ethane, your pool[49] verbatim) are physical constants from the taught pairs. Tokens {100, 162, 89} + 'water' are excused ONLY at seq 19 (slot-restricted); water everywhere else in the bank was content-removed (A#17 freshened).
3. SYMBOL/FORMULA POLICY (recorded adjudication - confirm the convention): element-NAME tokens whose referent is an ATOM inside a case molecule (the H-on-N/O/F checklist vocabulary) are written in course-canonical notation in scanned fields - N-H/O-H/C-H groups, 'the O atom', formulas (CO2, H2O2, NF3, ...; exported as Unicode subscripts). This is a content alignment (the course itself writes O-H/N-H/C-H), not a scanner dodge: wherever a substance NAME is the instance, the name stays and the scan sees it at its single ledger slot.
4. Seed census: ALL 57 pool seeds placed (form A 20 / B 19 / C 18 - your curation depth; forms D/E fully authored; 0 spares). Your 6 demo_curated items are POOL DUPLICATES (demo 0-5 = pool 33/34/35/51/52/53, stem-verified) - placed once each at seqs 12/13/18 with both refs cited. prod_seeds is EMPTY, so the FRQ is authored (next note). 23 of the 57 seeds carried a must_freshen_instance flag from the stage-1 freshness scan; SEED RULING freshenings to confirm: A#17's seed table was CMB-057's own student-seen check trio (H2O/H2S/O2) -> formic acid 101 / bromomethane 4 / ethene -104 C (real bps, fresh substances); A#15's ethanol/dimethyl-ether pair is CMB-051-spec-visible -> propan-2-ol / ethyl methyl ether (83 / 7 C, real); A#18's NaF -> strontium chloride 874 C (first swap LiF was itself CMB-059's WE example, caught by the gram scan). Structures, keys, and misconception classes verbatim throughout.
5. Zero NOTA/AOTA this gate: none of the 57 seeds carries a None/All-of-the-above seat, so the opportunistic replacement rule (ANSWERS #2) never fired. (The U5 CMB-028 keyed-NOTA v2-spec fix was verified not applicable at seed placement - CMB-028 is not in this gate's scope.)
6. FRQ design (confirm): seq 21 = authored unlabeled-solids classification on capstone CMB-059 (TEKS-CHEM-7D; your spec extraNotes names it the U5-G3 capstone): three crystalline solids, measured melting points in a rendered table -> (a) classify X and Y naming what melting must overcome in each (40), (b) correct the 'low melting point proves weak covalent bonds' claim (30), (c) classify Z from its melting point (30); rubric sums 100, parts split losslessly. Round-1 blind caught the five forms sharing near-identical FRQ stems - each form now has its own framing and solid labels (A X/Y/Z storeroom, B P/Q/R prep-room, C J/K/L stockroom, D F/G/H lab-bench tray, E R/S/T supply cupboard) renamed through parts, model answers, rubrics, and figure rows. Standing typed-plan flag applies.
7. Blind-round content fixes worth your eyes: (1) the round's one hard fail - a seq-12 checklist item whose subset options were rated defensible - was CLASS-SWEPT: all five seq-12 stems now demand the complete set ('Which choice lists ALL of the intermolecular forces acting between ...'); (2) B#18's key was verbatim-identical to its own form's FRQ part-(b) model answer -> rewritten to an ion-pairing-vs-lattice claim critique; C#18 rehearsed its FRQ's task -> rewritten to a named-substance contrast (vanillin 81 C / rubidium chloride 715 C); (3) B#15 had two options selecting the same substance (bare pick + pick-with-rationale, inherited from your seed's acetone-double pattern) -> one replaced with the similar-size dead-end misconception.
8. sol (authoritative cross-vendor QC) converged 12 -> 1 -> 0 -> 0 fails over 4 loops with ZERO overrides carried; rulings folded into content include: 'only dipole-dipole' phrasings corrected to 'strongest attraction is dipole-dipole' (the additive rule - dispersion acts between ALL molecules); the dispersion-size trend scoped to 'two similar substances' (CMB-048's like-with-like caveat); two TRUE-but-irrelevant distractors replaced with false-inference distractors (B#17, C#19); D#11's geometry distractor now names formic acid so it is judgeable. ONE checkable-fact dispute to flag: sol holds GeCl4's boiling point at ~83 C vs our 86-86.5 C sources (literature genuinely splits) - D#15's explanation now states the uncontested QUALITATIVE contrast (GeH4 boils at -88 C; GeCl4 is liquid well above room temperature) instead of quoting a disputed number. Flag if you hold a canonical GeCl4 value.
9. Recorded advisory classes (blind reviewers, not content-fixed - spec-design authority): mechanism keys quote the taught MECH-* sentences VERBATIM by spec mandate, so they draw longest-option/definition-echo flags (V-T4, the recorded hard bar, passes on all 105 items - shortening keys would break the verbatim-mechanism requirement); the seq 1->20 easy->hard ladder inside one topic places rule-statement items before rule-application items (cross-item-cueing flags; the two WORST instances - the FRQ echoes above - were content-fixed); B#20/D#15-class stems SUPPLY the force comparison (CMB-055 EXTRA mandates supplied comparisons; the tested link is forces -> boiling point).
10. gate_config ledger (all recorded, _shared untouched): 2 adjudicated_instance_families (notes 1-2 above) + 3 extra_task_idioms ('the claim is wrong because/only', 'the student is right' - option-side verdict openers of your claim-critique family, which the automatic idiom derivation does not harvest from option text). Instance hygiene: the fresh-instance set is classroom-safe throughout; zero uranium/plutonium/radium/actinide/enrichment/reactor/weapon/radiation framings bank-wide (re-swept at packaging, 0 hits). Documented-for-maintainer _shared candidates (READ-ONLY this wave, not applied): the molecule-pair blind-figure family (rendered by a gate-local augmenter, U2/U3 precedent) and the A7 force-name relief key that would retire these per-gate wrappers.
Dry ice — solid CO₂ — is packed with CO₂ molecules sitting close together. Compare the strength of a covalent C=O bond within one molecule with the attraction between two neighboring molecules.
The C=O bond is much stronger than the attraction between the neighboring molecules. KEY
In a solid, the attractions between molecules become stronger than the bonds within them.
The attraction between the neighboring molecules is much stronger, which is why the solid holds its shape.
The two attractions are equal, because the molecules in a solid are touching.
A student says the attraction between two iodine molecules in solid iodine is a covalent bond, 'because it holds them together.' What is the correct classification?
An intermolecular force — it acts between two I₂ molecules, and holding things together does not make an attraction a covalent bond. KEY
A covalent bond — anything that holds particles together is a covalent bond.
An intramolecular force — the two attracted molecules together count as one single bigger molecule of four iodine atoms.
Neither — there is no attraction between nonpolar molecules like I₂.
CMB-044 · medium · application · seq 5 · seed:U5-G3/pool[6] (CMB-044 gateItems) — FRESHENED per stage-1 flag: HCl/−85 °C -> SO2/−10 °C (the 'hydrogen atoms' gram is 044's own fluency text); misconception classes kept; swept · mcq4
SO₂ boils at −10 °C. A student claims the gas that forms is a mixture of loose S atoms and O atoms. What is wrong with the claim?
Boiling separates SO₂ molecules from one another without breaking the S=O bonds, so the gas is intact SO₂ molecules. KEY
Nothing is wrong — a gas is always made of single atoms.
The claim names the wrong products — the gas is actually a mixture of S₈ molecules and O₂ molecules.
The claim is wrong only because single atoms cannot exist as a gas.
A student claims that boiling liquid iodine monochloride, ICl, produces I₂ gas and Cl₂ gas. Use the strengths of the two kinds of attraction to correct the claim.
Boiling overcomes only the attractions between ICl molecules, because those attractions are much weaker than the I–Cl bonds within them — the gas is intact ICl molecules. KEY
The claim is right — boiling supplies enough energy to break the I–Cl bonds and regroup the atoms.
The claim is wrong only because the products would be single I and Cl atoms rather than two gases.
The claim is wrong because the attractions between ICl molecules are far too strong for boiling to overcome, so the liquid cannot boil at any temperature it could reach.
Ethane, C₂H₆, is nonpolar, with no permanent δ ends — yet at very low temperatures liquid ethane exists, its molecules held together. Explain the attraction.
A molecule's moving electrons can pile up on one side for a moment, giving it a temporary uneven charge that attracts its neighbor. KEY
Cooling gives each molecule a permanent negative charge, and those permanent charges hold the liquid's molecules together.
Ethane molecules are actually polar, with a permanent δ− end that was overlooked.
C–H bonds break at low temperature, and the freed electrons glue neighboring molecules together.
Hexane (50 electrons per molecule) and decane (82 electrons per molecule), are similar substances. Which comparison of their dispersion forces is correct?
Decane's are stronger, because its larger molecules carry more electrons. KEY
Hexane's are stronger, because a smaller molecule concentrates its charge imbalances.
The two are equal, because both substances are nonpolar.
Neither has dispersion forces, because their molecules carry no permanent charge.
A student explains dipole-dipole attraction this way: 'The molecules attract because each one's electrons pile up on one side for a moment.' What is wrong with the explanation?
It describes dispersion — dipole-dipole attraction comes from permanent δ ends: the slightly positive end of one polar molecule attracts the slightly negative end of the next. KEY
Nothing is wrong — momentary pile-ups are what create every attraction between molecules.
The explanation fails only in one small detail — in a real molecule the electrons pile up on both sides of the molecule at once, rather than crowding onto a single side.
The explanation fails because dipole-dipole attraction involves no charges of any kind.
CMB-051 · medium · application · seq 10 · seed:U5-G3/pool[27] (CMB-051 gateItems) — PATCHED per stage-1 flag: methylamine -> ethylamine (CH3NH2 sits verbatim on the adjacent seq-11 seed); hydrogen counts swept · mcq4
Ethylamine, C₂H₅NH₂, carries two hydrogens on its N atom and five on C atoms. Which of its hydrogens can hydrogen-bond with a neighboring molecule's N atom?
Only the two on the N atom. KEY
All seven of its hydrogens.
Only the five on C atoms.
None of them.
CMB-052 · medium · application · seq 11 · seed:U5-G3/pool[30] (CMB-052 gateItems) — PATCHED per stage-1 flag: CH3Cl -> CH3F throughout; the pull-comparison distractor re-grounded on fluorine (true premise, same wrong conclusion); swept · mcq4
Methylamine, CH₃NH₂ (N–H hydrogens), clings to its neighbors more strongly than fluoromethane, CH₃F (C–H hydrogens only), though both molecules are polar and similar in size. What explains the difference?
CH₃NH₂ hydrogen-bonds — its strongly positive N–H hydrogens get very close to neighboring lone pairs — while CH₃F can manage nothing stronger than dipole-dipole attraction. KEY
CH₃NH₂ molecules are far larger, so their dispersion forces overwhelm everything else.
The F atom pulls shared electrons more strongly than the N atom does, and that stronger pull weakens every attraction CH₃F molecules can make to their neighbors.
The N–H covalent bonds of one CH₃NH₂ molecule stretch across and bond to its neighbors.
CMB-053 · medium · application · seq 12 · seed:U5-G3/pool[33] (CMB-053 gateItems; demo_curated[0]) — PATCHED per stage-1 flag: methanol -> propan-1-ol (the all-three answer for methanol is 051's own fluency key); counts swept · mcq4
Propan-1-ol, C₃H₇OH, is polar; one of its hydrogens sits on the O atom and the other seven sit on C atoms. Which choice lists ALL of the intermolecular forces acting between propan-1-ol molecules?
Dispersion forces, dipole-dipole attractions, and hydrogen bonding KEY
Dispersion forces and dipole-dipole attractions
Dispersion forces and hydrogen bonding
Dispersion forces only
CMB-053 · medium · application · seq 13 · seed:U5-G3/pool[35] (CMB-053 gateItems; demo_curated[2]) — PATCHED per stage-1 flag: dispersion-ALONE key liquid N2 -> CS2 (N2's dispersion-only status is 046's own rule line 2); swept · mcq4
Four liquids: SiBr₄ (nonpolar), CH₃I (polar; C–H hydrogens only), propylamine C₃H₇NH₂ (polar; two N–H bonds), and H₂O₂ (polar; two O–H groups). Between which liquid's molecules do dispersion forces act ALONE?
PH₃ molecules are polar; SiH₄ molecules, of similar size, are nonpolar. Which comparison of the attractions between their molecules is correct?
PH₃ molecules grip their neighbors more strongly. KEY
SiH₄ molecules grip their neighbors more strongly.
The attractions are exactly equal.
The two cannot be compared without exact numbers.
CMB-055 · medium · application · seq 15 · seed:U5-G3/pool[39] (CMB-055 gateItems) — VERBATIM (spec-planned gate pair; post-answer bp values are real, spec-sanctioned confirmation) · mcq4
Propan-2-ol, C₃H₇OH, forms hydrogen bonds at its O–H group. Ethyl methyl ether, CH₃OC₂H₅, contains exactly the same atoms but has no O–H group, so dipole-dipole attractions are the strongest ones its molecules can manage. Which substance boils at the higher temperature?
Propan-2-ol KEY
Ethyl methyl ether
Both boil at the same temperature, because they contain the same atoms
It cannot be predicted, because the two molecules are the same size
CMB-056 · medium · application · seq 16 · seed:U5-G3/pool[43] (CMB-056 gateItems) — PATCHED per stage-1 flag: the −196 °C value dropped (046's own hook value); all else verbatim · mcq4
Liquid N₂ boils far below room temperature. Explain the very low boiling point in terms of the energy needed to separate N₂ molecules.
Only weak dispersion forces act between N₂ molecules, so little energy is needed to pull them apart, and boiling happens at a very low temperature. KEY
The N≡N bond is weak, so the molecules fall apart with almost no heating.
N₂ molecules repel one another, so no energy is needed to separate them.
Very cold liquids have no intermolecular forces at all, so liquid N₂ boils away the moment it forms without any energy being supplied.
CMB-057 · hard · transfer · seq 17 · seed:U5-G3/pool[45] (CMB-057 gateItems) — VERBATIM; figure payload authored from the seed's own explanation values · mcq4
The table gives the boiling point measured for each of three substances. Which substance has the strongest intermolecular forces?
Melting solid stearic acid works by breaking the covalent bonds inside its molecules, and those bonds are weaker than the ionic bonds inside strontium chloride.
Strontium chloride melts higher because each Sr²⁺ ion is attracted to just one Cl⁻ partner very strongly.
Both solids are held by intermolecular forces, but strontium chloride's molecules are more polar.
CMB-058 · hard · transfer · seq 19 · seed:U5-G3/pool[48] (CMB-058 gateItems) — VERBATIM (rule-content cluster: water/100 °C; CO partner fresh vs student-seen) · mcq4
CO is close to water in molecular size, yet CO boils at −192 °C and water at 100 °C. A student explains: 'Water must be far heavier than CO.' Which explanation is correct?
Water boils far higher because its hydrogen bonding is much stronger than the attractions between CO molecules. KEY
The student is right — water molecules really are many times heavier than CO molecules, and molecular mass is what sets the boiling point.
Water boils higher because each H₂O molecule contains more covalent bonds than each CO molecule.
Water boils higher because CO molecules repel one another instead of attracting.
CMB-060 · hard · transfer · seq 20 · seed:U5-G3/pool[54] (CMB-060 gateItems) — FRESHENED per stage-1 flag: 'nonpolar waxes' -> 'nonpolar oils' (wax = 060's own rule-line instance) and the key recast onto the tears' molecules (bare 'water' minimized per the cluster plan); misconception classes kept; swept · mcq4
Waterproof mascara is made with nonpolar oils, and it stays put through tears. Which statement explains why the nonpolar oils stay put through tears?
The molecules in tears grip one another far more strongly than they grip the nonpolar oils, so tears run off without carrying the mascara away. KEY
The nonpolar oils hydrogen-bond directly to the eyelashes, and no tear can ever break a hydrogen bond once it has formed between them.
The oils react chemically with tears, hardening into a waterproof shell.
Tears are repelled because the oil molecules carry a negative charge that pushes them away.
CMB-059 · medium · application · seq 21 · authored (U5-G3 has zero prod seeds — blueprint directs an authored unlabeled-solids classification FRQ from capstone CMB-059, extending the pool-53 unknown-solid genre; values are real melting points, provenance: X=KBr 734, Y=benzoic acid 122, Z=MgCl2 714 (provenance only — solids stay unlabeled); instance set disjoint from the lesson's taught set and the placed seeds) · frq
A storeroom drawer holds three unlabeled crystalline solids, marked only X, Y, and Z. A technician measures each solid's melting point; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
A storeroom drawer holds three unlabeled crystalline solids, marked only X, Y, and Z. A technician measures each solid's melting point; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
(a) Classify solid X and solid Y as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
(b) A classmate says solid Y's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
(c) Classify solid Z and justify your classification using its melting point.
Part a. Classify solid X and solid Y as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
Model: Solid X (melting point 734 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid Y (melting point 122 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
Part b. A classmate says solid Y's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
Model: Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 122 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
Part c. Classify solid Z and justify your classification using its melting point.
Model: Solid Z melts at 714 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
Full model answer. (a) Solid X (melting point 734 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid Y (melting point 122 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
(b) Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 122 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
(c) Solid Z melts at 714 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
Pulling one HF molecule away from its neighbor takes energy, and breaking the H–F bond inside one molecule also takes energy. Which takes more, and by how much?
Breaking the H–F bond takes far more energy — the difference is large, not slight. KEY
Pulling the molecule away from its neighbor takes far more energy.
Breaking the bond takes slightly more energy — the two are nearly equal.
Neither takes energy, because attractions release energy when they act.
A student says: 'Nonpolar molecules cannot attract each other, because they have no charged ends.' What is wrong with the claim?
All molecules attract their neighbors through dispersion forces, so nonpolar molecules still attract — the student's rule leaves dispersion out. KEY
Nothing is wrong — attraction between molecules always needs permanent charged ends.
The claim is wrong because nonpolar molecules attract each other with weak covalent bonds that form and break between the molecules.
The claim is wrong because every molecule secretly has permanent δ+ and δ− ends.
CMB-049 · easy · recall · seq 3 · seed:U5-G3/pool[23] (CMB-049 gateItems) — VERBATIM; placed at form B by the stage-1 row-order tweak · mcq4
PBr₃ is a polar molecule; N₂ is nonpolar. Between which substance's molecules do dipole-dipole attractions act?
PBr₃ only KEY
N₂ only
Both PBr₃ and N₂
Neither substance
CMB-042 · easy · application · seq 4 · seed:U5-G3/pool[1] (CMB-042 gateItems) — FRESHENED per stage-1 flag: CH4 (042's own fluency instance) -> CH3Cl; labeled bond Y = the C–Cl bond; structure/misconceptions kept; feedback-leftover sweep clean · mcq4
The figure shows two CH₃Cl molecules side by side. The dashed line running from one molecule to the other is labeled X, and the solid C–Cl bond inside one molecule is labeled Y. Which classification pairs X and Y correctly?
FIGURE (molecule-pair · stimulus) — molecules: [{"formula": "CH₃Cl", "sketch": "one carbon circle bonded to three small hydrogen circles and one larger chlorine circle, bonds as solid lines"}, {"formula":… · annotations: [{"target": "dashed line from the first molecule to the second", "label": "X"}, {"target": "the solid C–Cl bond line inside the first molecule", "label": "Y"}] · style: "dashed-between vs solid-within line convention (unit IMF figure convention)" · blindDescription: "Two identical CH₃Cl molecules drawn side by side; a dashed line labeled X runs between the two molecules; the solid line labeled Y is the C–Cl bond inside o…raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "molecule-pair",
"molecules": [
{
"formula": "CH₃Cl",
"sketch": "one carbon circle bonded to three small hydrogen circles and one larger chlorine circle, bonds as solid lines"
},
{
"formula": "CH₃Cl",
"sketch": "identical second molecule placed nearby"
}
],
"annotations": [
{
"target": "dashed line from the first molecule to the second",
"label": "X"
},
{
"target": "the solid C–Cl bond line inside the first molecule",
"label": "Y"
}
],
"style": "dashed-between vs solid-within line convention (unit IMF figure convention)",
"blindDescription": "Two identical CH₃Cl molecules drawn side by side; a dashed line labeled X runs between the two molecules; the solid line labeled Y is the C–Cl bond inside one molecule."
}
}
A sample of Cl₂ gas is cooled until it becomes a liquid. What happens to its Cl₂ molecules?
They move closer together, and the same intact Cl₂ molecules make up the liquid. KEY
Pairs of molecules bond covalently into Cl₄ molecules as the liquid forms.
The molecules split into single Cl atoms, which then pack together as the liquid.
The molecules link into one giant connected molecule that fills the container.
CMB-045 · medium · application · seq 6 · seed:U5-G3/pool[10] (CMB-045 gateItems) — PATCHED per stage-1 flag: the −78 °C value dropped (collides with 045's own ethanol-78 fluency value); instance and misconception classes kept · mcq4
Solid CO₂ passes straight into the gas state as it warms, without a single C=O bond breaking. Why do the molecules separate from one another before any bond breaks?
Because the attractions between molecules are much weaker than the bonds within them, so the attractions between molecules give way first. KEY
Because C=O double bonds cannot be broken by any amount of energy.
Because at such a low temperature the molecules have no energy, so only the loosest arrangement can change.
Because the attractions between CO₂ molecules turn into pushes as the solid warms, driving the molecules apart without any energy cost.
Two similar substances are being compared. A student says: 'Small molecules have stronger dispersion forces, because their electrons are packed closer together.' What is the correct trend for such substances, and why?
Larger molecules have stronger dispersion forces, because they have more electrons, so the momentary charge imbalances are larger and the attractions stronger. KEY
The student is right — tighter packing makes each electron pile-up more intense.
Larger molecules have stronger dispersion forces, because their covalent bonds are harder to break, and harder-to-break bonds grip neighboring molecules.
All molecules have equally strong dispersion forces, because all electrons move at the same speed.
CMB-050 · medium · application · seq 9 · seed:U5-G3/pool[25] (CMB-050 gateItems) — MICRO-REWORDED per stage-1 flag: 'a δ+ end at the hydrogens' -> 'a δ+ end on its CH₃ side' (bare 'hydrogen' is 050's own δ-end vocabulary); all else verbatim · mcq4
In liquid CH₃F, each polar molecule has a δ− end at its F atom and a δ+ end on its CH₃ side. How does a neighboring CH₃F molecule orient itself toward one molecule's F end?
It turns its δ+ end toward the F end. KEY
It turns its own δ− F end toward the F end.
It turns sideways so that neither of its ends faces the F end.
It keeps whatever orientation it had, because orientation does not matter to the attraction.
CMB-051 · medium · application · seq 10 · seed:U5-G3/pool[28] (CMB-051 gateItems) — VERBATIM apart from one mechanical notation normalization: the ionic-bond distractor's ion symbols set in Unicode (H⁺ / O²⁻) per the course notation mandate · mcq4
H₂O₂ molecules attract one another through hydrogen bonding. Which statement about one of those hydrogen bonds is correct?
It is an attraction between two molecules, much weaker than the O–H covalent bonds within each molecule. KEY
It is a covalent bond that joins the two molecules into one larger H₄O₄ molecule.
It is stronger than the O–H covalent bonds within each molecule.
Four liquids: CH₃OCH₃ (polar; C–H hydrogens only), acetic acid (polar; one O–H group), HI (polar; its H bonded to I), and octane (nonpolar). Between which liquid's molecules does hydrogen bonding act?
Acetic acid KEY
Dimethyl ether, CH₃OCH₃
HI
Octane
CMB-054 · medium · application · seq 14 · seed:U5-G3/pool[37] (CMB-054 gateItems) — PATCHED per stage-1 flag: HCl -> HBr (HCl is 054's own WE instance); swept · mcq4
I₂ molecules are much larger than HBr molecules. Can the weakest-to-strongest ranking be used to compare the attraction between I₂ molecules with the attraction between HBr molecules?
No — the ranking holds only for molecules of similar size, and these sizes are very different. KEY
Yes — HBr is polar, so its dipole-dipole attractions are automatically the stronger ones.
Yes — a ranking of forces holds in every situation once it is established.
No — because I₂ is nonpolar, it has no intermolecular forces to compare.
CMB-055 · medium · application · seq 15 · seed:U5-G3/pool[40] (CMB-055 gateItems) — FRESHENED per stage-1 flag: partner CH3F (055's own fluency partner) -> butanal; feedback made qualitative (values dropped); misconception classes kept; swept · mcq4
Butan-2-ol can hydrogen-bond, using its O–H group. Butanal, of similar molecular size, is polar but cannot hydrogen-bond. Which substance has the higher boiling point?
Butan-2-ol KEY
Butanal
Both boil at the same temperature, because both are polar
It cannot be predicted, because the two molecules are so similar in size.
Separating neighboring CH₃OH molecules takes more energy than separating neighboring C₂H₆ molecules of similar size. What follows for the two boiling points, and why?
CH₃OH boils higher, because boiling has to pull molecules away from each other, so stronger attractions need more energy to overcome. KEY
C₂H₆ boils higher, because molecules with weak attractions store more energy for boiling.
Both boil at the same temperature, because the energy cost of separating molecules has no effect on when a liquid boils.
CH₃OH cannot boil at all, because its attractions are too strong to overcome.
CMB-057 · hard · transfer · seq 17 · seed:U5-G3/pool[47] (CMB-057 gateItems) — VERBATIM; figure payload authored from the seed's own explanation values · mcq4
Silane and silicon tetrachloride are both compounds of silicon. Using the boiling points in the table, which conclusion is supported by the data?
SiCl₄ molecules attract each other more strongly than SiH₄ molecules do. KEY
SiH₄ molecules attract each other more strongly than SiCl₄ molecules do.
SiCl₄ boils higher because boiling breaks its Si–Cl covalent bonds, and those bonds are stronger than Si–H bonds.
The data support no conclusion, because the two compounds contain different elements.
CMB-059 · hard · transfer · seq 18 · seed:U5-G3/pool[52] (CMB-059 gateItems; demo_curated[4]) — VERBATIM · mcq4
A student writes: 'Ionic solids melt at high temperatures because each ion grips a single partner ion, and breaking those one-to-one partnerships takes extreme heat.' What is wrong with the claim?
No ion pairs off with a single partner — melting must overcome charge attractions acting in every direction through the whole lattice. KEY
Nothing is wrong — every ionic solid is built from separate ion pairs, each pair standing alone.
The claim is wrong only because the partnerships are easy to break, which is why ionic solids actually melt at low temperatures.
The claim is wrong because ionic solids are held together by the same weak attractions that hold molecular solids.
CMB-058 · hard · transfer · seq 19 · seed:U5-G3/pool[49] (CMB-058 gateItems) — VERBATIM (rule-content cluster) · mcq4
Ethane, C₂H₆, boils at −89 °C. Water, a molecule of smaller size, boils at 100 °C. Which of these explains water's higher boiling point?
Hydrogen bonding among water's molecules is much stronger than the dispersion forces between ethane molecules. KEY
Smaller molecules always boil at higher temperatures than larger ones, and water is the smaller molecule here.
Water is a compound while ethane is an element, and compounds boil higher.
Ethane's C–H bonds break at low temperature, letting it boil early.
CMB-060 · hard · transfer · seq 20 · seed:U5-G3/pool[55] (CMB-060 gateItems) — FRESHENED per stage-1 flag: spilled water -> rubbing alcohol (removes the bare-water adjacency with the all-water seq 19; cellulose kept); misconception classes kept; swept · mcq4
Paper towels are made of cellulose fibers whose molecules carry many O–H groups. Rubbing alcohol — a small molecule with an O–H group of its own — spills on a counter. Why does the towel soak up the spill so effectively?
The O–H groups all along the fibers form hydrogen bonds with the alcohol molecules, pulling the spill into the towel and holding it there. KEY
Cellulose is nonpolar, so the alcohol beads up inside the towel and stays trapped.
The towel's fibers dissolve into the alcohol and thicken it into a gel.
Alcohol molecules are small enough to hide in the gaps between fibers, and any fiber material with the same gaps would hold them equally well.
CMB-059 · medium · application · seq 21 · authored (U5-G3 has zero prod seeds — blueprint directs an authored unlabeled-solids classification FRQ from capstone CMB-059, extending the pool-53 unknown-solid genre; values are real melting points, provenance: P=sulfur 115, Q=KI 681, R=white phosphorus 44; instance set disjoint from the lesson's taught set and the placed seeds) · frq
A prep-room cabinet holds three unlabeled crystalline solids, marked only P, Q, and R. A technician measures each solid's melting point; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
A prep-room cabinet holds three unlabeled crystalline solids, marked only P, Q, and R. A technician measures each solid's melting point; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
(a) Classify solid Q and solid P as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
(b) A classmate says solid P's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
(c) Classify solid R and justify your classification using its melting point.
Part a. Classify solid Q and solid P as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
Model: Solid Q (melting point 681 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid P (melting point 115 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
Part b. A classmate says solid P's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
Model: Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 115 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
Part c. Classify solid R and justify your classification using its melting point.
Model: Solid R melts at 44 °C — a low melting point, so it is molecular: melting only has to overcome the weak attractions between its intact molecules, which takes little energy.
Full model answer. (a) Solid Q (melting point 681 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid P (melting point 115 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
(b) Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 115 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
(c) Solid R melts at 44 °C — a low melting point, so it is molecular: melting only has to overcome the weak attractions between its intact molecules, which takes little energy.
Liquid N₂ contains N≡N triple bonds within its molecules and attractions between neighboring N₂ molecules. Which pairing of classifications is correct?
The N≡N bond is intramolecular; the attraction between neighboring molecules is intermolecular. KEY
The N≡N bond is intermolecular; the attraction between neighboring molecules is intramolecular.
Both are intramolecular, because N₂ molecules contain only one element.
Both are intermolecular, because a triple bond is three attractions.
CO₂ (22 electrons per molecule) and CS₂ (38 electrons per molecule), are similar substances. Which has the stronger dispersion forces, and what makes the difference?
CS₂ — larger molecules have more electrons, so the momentary charge imbalances are larger and the attractions stronger. KEY
CO₂ — smaller molecules hold their electrons more tightly, and that tighter holding strengthens the momentary imbalances.
CS₂ — its S atoms form weak covalent bonds to neighboring molecules.
Neither — dispersion strength is identical for all nonpolar substances.
CMB-050 · medium · application · seq 9 · seed:U5-G3/pool[26] (CMB-050 gateItems) — FRESHENED per stage-1 flag: ClF/F2 -> NF3/N2 ('δ+ chlorine end' collides with 050's own WE); δ sides supplied; misconception classes kept; swept · mcq4
NF₃ is polar: its F atoms form the δ− side and its N side is δ+. N₂ is nonpolar. Why do NF₃ molecules attract through dipole-dipole attractions while N₂ molecules do not?
NF₃ molecules have permanent δ+ and δ− sides that attract each other; N₂ molecules have no permanent δ sides. KEY
N₂ molecules have no moving electrons, so they cannot attract anything.
NF₃ molecules form weak covalent bonds to their neighbors, while N₂ molecules cannot form any.
N₂ molecules are too small for any attraction to reach between them.
CMB-051 · medium · application · seq 10 · seed:U5-G3/pool[29] (CMB-051 gateItems) — VERBATIM (its carbon/fluorine/hydrogen words are the qualifying-condition vocabulary — rule-content cluster, recorded) · mcq4
A student says CH₃F molecules hydrogen-bond with each other, because the molecule contains both H and F atoms. What is wrong with the claim?
In CH₃F every one of the hydrogens is a C–H — hydrogen bonding needs an H atom covalently bonded to N, O, or F. KEY
Nothing is wrong — a molecule that contains both H and F atoms anywhere in its structure hydrogen-bonds.
The claim is wrong because F atoms never take part in hydrogen bonding.
A student says: 'Hydrogen bonds are strong because the H atom is shared between two molecules, half-bonded to each.' What is the correct picture?
The H atom stays covalently bonded to its own molecule — the strength comes from that strongly positive H getting very close to a lone pair on the neighboring molecule. KEY
The student is right — the H atom forms half a covalent bond to each of the two molecules, and the two half-bonds together are what make the attraction so strong.
The strength actually comes from the two molecules exchanging electrons back and forth.
Hydrogen bonds are not strong at all compared with the other attractions between molecules.
CMB-053 · medium · application · seq 12 · authored (dispersion-only checklist case; fresh instance SiF₄, polarity supplied; options = bare force-combination labels per R11) · mcq4
Silicon tetrafluoride, SiF₄, is a nonpolar molecule, and it contains no H atoms. Which choice lists ALL of the intermolecular forces acting between SiF₄ molecules?
Dispersion forces only KEY
Dispersion forces and dipole-dipole attractions
Dispersion forces, dipole-dipole attractions, and hydrogen bonding
Four liquids: hexane (nonpolar), PH₃ (polar; its hydrogens are all P–H), ethylene glycol (polar; two O–H groups), and CCl₄ (nonpolar). Between which liquid's molecules do EXACTLY TWO of the three intermolecular forces act?
PH₃ KEY
Hexane
Ethylene glycol
CCl₄
CMB-054 · medium · application · seq 14 · seed:U5-G3/pool[38] (CMB-054 gateItems) — FRESHENED per stage-1 flag: the seed trio C2H6/CH3F/CH3OH reuses 054's own WE substances -> fresh similar-size trio propene/acetaldehyde/ethanol; rank logic and misconception classes kept; swept · mcq4
Three substances have molecules of similar size: propene C₃H₆ (nonpolar), acetaldehyde CH₃CHO (polar, no hydrogen bonding), and C₂H₅OH, ethanol (hydrogen-bonding). Rank the attractions between their molecules from weakest to strongest.
C₃H₆, then CH₃CHO, then C₂H₅OH KEY
C₂H₅OH, then CH₃CHO, then C₃H₆
CH₃CHO, then C₃H₆, then C₂H₅OH
C₃H₆, then C₂H₅OH, then CH₃CHO
CMB-055 · medium · application · seq 15 · seed:U5-G3/pool[41] (CMB-055 gateItems) — FRESHENED per stage-1 flag: CH3OH (055's own fluency instance) -> methanol; feedback made qualitative (values dropped); misconception classes kept; swept · mcq4
Three substances have molecules of similar size: silane SiH₄ (nonpolar), phosphine PH₃ (polar, no hydrogen bonding), and methanol CH₃OH (hydrogen-bonding). Which boils at the LOWEST temperature?
Silane, SiH₄ KEY
Phosphine, PH₃
Methanol, CH₃OH
All three boil at the same temperature
CMB-056 · medium · application · seq 16 · seed:U5-G3/pool[42] (CMB-056 gateItems) — FRESHENED per stage-1 flag: the water-bond-claim runs on the liquid's, value-free (water + 100 °C are reserved to the CMB-058 rule-content cluster; the all-water seq-19 row makes any 056 water item an adjacency risk); misconception classes kept; swept · mcq4
A student says: 'When a molecular liquid finally boils, the heat has become strong enough to break the covalent bonds inside its molecules — that is what boiling is.' What is the correct explanation?
The heat overcomes the attractions BETWEEN the liquid's molecules — boiling has to pull molecules away from each other, and every covalent bond survives. KEY
The student is right — boiling always breaks the covalent bonds within molecules.
The student is almost right — boiling breaks about half of the covalent bonds.
No heat is needed at all, because the attractions between the liquid's molecules give way on their own once the liquid is left standing.
CMB-057 · hard · transfer · seq 17 · seed:U5-G3/pool[46] (CMB-057 gateItems) — FRESHENED per stage-1 flag: CO/CH3F (−78 = 057's own ethanol fluency value) -> HBr/HI; farther-from-zero trap and misconception classes kept; swept · mcq4
A student reads the table and concludes that HBr has stronger intermolecular forces than HI, 'because HBr boils at the more extreme temperature.' What do the data actually show?
HI has the stronger intermolecular forces, because −35 °C is a higher temperature than −67 °C. KEY
HBr has the stronger intermolecular forces, because −67 °C is farther from zero.
HBr has the stronger intermolecular forces, because it boils at the colder temperature.
The two substances have equally strong intermolecular forces, because both boiling points are below zero.
CMB-059 · hard · transfer · seq 18 · seed:U5-G3/pool[53] (CMB-059 gateItems; demo_curated[5]) — VERBATIM (the unknown-solid genre the FRQ extends; FRQ instance sets kept disjoint) · mcq4
Vanillin, a molecular solid, melts at 81 °C. Rubidium chloride, an ionic solid, melts at 715 °C. Which statement accounts for the two values?
Melting vanillin overcomes weak attractions between intact molecules; melting rubidium chloride overcomes charge attractions running through its whole lattice. KEY
Melting vanillin works by breaking the covalent bonds inside its molecules, and those bonds happen to be weaker than rubidium chloride's ionic bonds.
Rubidium chloride melts higher because each Rb⁺ ion holds on to exactly one Cl⁻ partner with enormous strength.
Both solids are held by the same kind of attraction, but vanillin's crystals are smaller and give way sooner.
CMB-058 · hard · transfer · seq 19 · seed:U5-G3/pool[50] (CMB-058 gateItems) — VERBATIM (rule-content cluster; 'salt' option word cross-059 warn recorded) · mcq4
Life on Earth depends on lakes and oceans staying liquid at everyday temperatures. Which fact about water makes that possible?
Hydrogen bonding holds water molecules together strongly enough that water stays liquid up to 100 °C. KEY
Water molecules are simply too heavy for everyday warmth to lift them out of the liquid and up into a gas.
Dissolved salts in seawater stop the water molecules from escaping.
Water can only become a gas by breaking its O–H covalent bonds, and everyday warmth is far too weak to break them.
CMB-060 · hard · transfer · seq 20 · seed:U5-G3/pool[56] (CMB-060 gateItems) — FRESHENED per stage-1 flag: fluoropolymer (060's own WE instance) -> polyethylene cutting board; the one bare-water option reworded to 'watery mess'; misconception classes kept; swept · mcq4
A student says a polyethylene cutting board is easy to wipe clean 'because its molecules are extremely heavy, and heavy molecules cannot hold dirt.' Which correction gives the real molecular reason?
The surface molecules are nonpolar, so watery messes attract themselves more strongly than the board attracts them and wipe away easily. KEY
The student is right — the heavier a material's molecules are, the less strongly the material can attract anything that lands on its surface.
The board's molecules are strongly polar, and polar surfaces never hold a watery mess.
The board is easy to clean because its surface molecules constantly slide off with the mess.
CMB-059 · medium · application · seq 21 · authored (U5-G3 has zero prod seeds — blueprint directs an authored unlabeled-solids classification FRQ from capstone CMB-059, extending the pool-53 unknown-solid genre; values are real melting points, provenance: J=BaCl2 962, K=urea 133, L=NaI 661; instance set disjoint from the lesson's taught set and the placed seeds) · frq
Three unlabeled crystalline solids, marked only J, K, and L, sit on a stockroom shelf. A lab assistant measures the melting point of each solid; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
Three unlabeled crystalline solids, marked only J, K, and L, sit on a stockroom shelf. A lab assistant measures the melting point of each solid; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
(a) Classify solid J and solid K as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
(b) A classmate says solid K's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
(c) Classify solid L and justify your classification using its melting point.
Part a. Classify solid J and solid K as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
Model: Solid J (melting point 962 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid K (melting point 133 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
Part b. A classmate says solid K's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
Model: Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 133 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
Part c. Classify solid L and justify your classification using its melting point.
Model: Solid L melts at 661 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
Full model answer. (a) Solid J (melting point 962 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid K (melting point 133 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
(b) Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 133 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
(c) Solid L melts at 661 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
Substance X is a molecular substance. A sample of it contains covalent bonds within its molecules and attractions between neighboring molecules. Which ranking of the two is correct?
The covalent bonds within the molecules are much stronger than the attractions between the molecules. KEY
The attractions between the molecules are much stronger than the covalent bonds within them.
The two are equal in strength, because both are attractions involving the same molecules.
It depends on the substance — in some molecular substances the attractions between molecules are the stronger ones.
Phosphorus trichloride, PCl₃, is a polar molecule. Its permanent δ+ and δ− ends attract the oppositely charged ends of neighboring PCl₃ molecules. What is this attraction called?
A dipole-dipole attraction. KEY
A dispersion force.
A covalent bond between the two molecules.
An ionic bond between the molecules' charged ends.
CMB-042 · easy · application · seq 4 · authored (which-of-four coverage facet — the FLU[1] class with fresh members; instances HBr / ethane / CO₂ recorded in the ledger) · mcq4
Which of these is an intermolecular force?
The attraction between one HBr molecule and a neighboring HBr molecule. KEY
The H–Br covalent bond joining the two atoms inside one HBr molecule.
When solid CBr₄ melts, its molecules separate from their fixed positions, yet every CBr₄ molecule survives in one piece. Why does the weaker attachment fail first?
Because the attractions between molecules are much weaker than the bonds within them, so the attractions between molecules give way first. KEY
Because the C–Br bonds strengthen as the solid warms, protecting the molecules.
Because melting strains only the attractions between molecules and never puts any strain at all on the covalent bonds within them.
Because the molecules take turns breaking and re-forming their covalent bonds as they come loose.
Carbon tetrachloride, CCl₄, is nonpolar, yet at room temperature it is a liquid whose molecules attract their neighbors. Why do CCl₄ molecules attract one another?
Because a molecule's moving electrons can pile up on one side for a moment, giving it a temporary uneven charge that attracts its neighbor. KEY
Because each CCl₄ molecule secretly keeps a permanent δ− end and a permanent δ+ end that the nonpolar label overlooks.
Because weak covalent bonds keep forming and breaking between neighboring molecules.
Because neighboring molecules trade electrons back and forth as they collide.
CMB-048 · medium · application · seq 8 · authored (fresh like-with-like pair, counts supplied per the 048 mandate; heptane/nonane fresh course-wide, real counts) · mcq4
Heptane (58 electrons per molecule) and nonane (74 electrons per molecule), are similar substances. Which comparison of their dispersion forces is correct?
Nonane's are stronger, because its larger molecules carry more electrons. KEY
Heptane's are stronger, because fewer electrons make each momentary pile-up easier to form.
The two are equal, because both substances are nonpolar.
Neither has dispersion forces, because neither molecule carries a permanent charge.
H₂S molecules are polar: a δ− side at the S atom and a δ+ side opposite it. In liquid H₂S, which arrangement do the neighboring molecules prefer?
The δ+ side of one molecule beside the δ− S side of its neighbor. KEY
The δ− S side of one molecule beside the δ− S side of its neighbor.
The molecules keep as far from one another as possible, avoiding contact.
No favored arrangement — the sides pair up completely at random.
CMB-051 · medium · application · seq 10 · authored (which-liquid pick — FLU[2] class with fresh members; attachments supplied per substance; instance uses recorded in the ledger) · mcq4
In which liquid do the molecules attract one another through hydrogen bonding?
Glycerol — each of its molecules carries three O–H groups. KEY
Phosphine, PH₃ — every one of its hydrogens is a P–H.
A formic acid molecule, HCOOH, carries exactly two hydrogens: one on the O atom and one on the C atom, both at the molecule's surface. Why can only the H atom on the O side anchor a hydrogen bond toward a neighboring molecule?
The O atom pulls the shared electrons so strongly that its attached H ends up strongly positive; the C atom's weaker pull leaves its H only mildly charged. KEY
The H atom on the C side is buried inside the molecule where no neighbor can reach it.
The H atom on the O side carries a full 1+ charge, and full charges are what hydrogen bonds need.
The O atom lends its H atom a share of extra electrons, and those extra electrons then reach across the gap to grip the neighboring molecule.
Dichloromethane, CH₂Cl₂, is polar; both of its hydrogens sit on the C atom. Which choice lists ALL of the intermolecular forces acting between CH₂Cl₂ molecules?
Dispersion forces and dipole-dipole attractions KEY
Dispersion forces, dipole-dipole attractions, and hydrogen bonding
Dipole-dipole attractions only
Dispersion forces only
CMB-053 · medium · application · seq 13 · authored (dipole-dipole-without-H-bonding pick; chloroethane fresh; propylamine = 053's rule-4 taught example used as a rule-content FOIL, recorded; SiCl₄ 17B cross-form recorded) · mcq4
Four liquids: chloroethane C₂H₅Cl (polar; all of its hydrogens are C–H), hexane (nonpolar), propylamine (polar; N–H bonds), and SiCl₄ (nonpolar). Between which liquid's molecules do dipole-dipole attractions act WITHOUT hydrogen bonding?
Propanal molecules are polar but form no hydrogen bonds; butane molecules, of similar size, are nonpolar. Which substance's molecules attract one another more strongly?
Propanal's — at similar size, dispersion plus dipole-dipole beats dispersion alone. KEY
Butane's — nonpolar molecules always grip hardest, because nothing distracts their electrons.
The attractions are equal, because the molecules are the same size.
The comparison needs hydrogen bonding data before it can be made.
CMB-055 · medium · application · seq 15 · authored (nonpolar size pair with the force comparison supplied; GeH₄/GeCl₄ cross-form uses (14C, 8D) recorded) · mcq4
Germane, GeH₄, and germanium tetrachloride, GeCl₄, are similar nonpolar substances, and GeCl₄'s larger molecules give it the stronger dispersion forces. Which substance boils at the higher temperature?
GeCl₄ KEY
GeH₄
Both boil at the same temperature, because both are nonpolar
Pulling neighboring CH₃NH₂ molecules apart takes more energy than pulling neighboring silane, SiH₄, molecules apart; the two molecules are similar in size. What follows for the two boiling points, and why?
Methylamine boils higher, because boiling has to pull molecules away from each other, so stronger attractions need more energy to overcome. KEY
Silane boils higher, because molecules with weak attractions hold on to more of their own energy and store it up for the boil.
Both boil at the same temperature, because similar-size molecules always need the same energy to separate.
Methylamine cannot boil at all, because its attractions are too strong to overcome.
CMB-057 · hard · transfer · seq 17 · authored (table-read facet; real values pentan-1-ol 97 / cyclohexane 81 °C in the figure only; cross-form uses (12A pentan-1-ol, 2D/8C/13 cyclohexane) recorded) · mcq4
The two liquids in the table were boiled and their boiling points recorded. Which conclusion about their intermolecular forces do the data support?
Pentan-1-ol's molecules attract one another more strongly than cyclohexane's do. KEY
Cyclohexane's molecules attract one another more strongly than pentan-1-ol's do.
Pentan-1-ol's covalent bonds are stronger than cyclohexane's covalent bonds.
The data support no conclusion, because the two liquids contain different elements.
CMB-059 · hard · transfer · seq 18 · authored (two-solid explanation with fresh real pair aspirin 135 / CsCl 645 °C; MECH-LATTICE verbatim; values disjoint from taught set + FRQ sets) · mcq4
Aspirin, a molecular solid, melts at 135 °C. Cesium chloride, an ionic solid, melts at 645 °C. Why do the two melting points differ so much?
Melting aspirin overcomes weak attractions between intact molecules; melting cesium chloride overcomes charge attractions acting in every direction through its lattice. KEY
Melting aspirin works by breaking the covalent bonds inside its molecules, and those covalent bonds are weaker than the ionic bonds inside cesium chloride.
Cesium chloride melts higher because each of its ions pairs off with exactly one neighbor very strongly.
Both solids are held by intermolecular forces, but cesium chloride's molecules are more polar.
CMB-058 · hard · transfer · seq 19 · authored (fence-partner variant on the rule-line pair CH₄/−162 vs water/100 — inside the recorded rule-content cluster; MECH-IMF-BOIL verbatim in the explanation) · mcq4
CH₄ is about the same size as a water molecule, yet the two substances sit far apart: CH₄ boils away at −162 °C while water lasts to 100 °C. What explains the enormous gap?
Water molecules grip one another through hydrogen bonds far stronger than the dispersion forces between CH₄ molecules. KEY
Water molecules are far heavier than CH₄ molecules, and mass sets the boiling point.
CH₄'s C–H bonds break at low temperature, letting it boil early.
The O–H covalent bonds in water are stronger than the C–H bonds in CH₄, and boiling is the process of breaking those covalent bonds.
CMB-060 · hard · transfer · seq 20 · authored (shed-design case, fresh instance; 'moisture/wet snow' phrasing keeps bare 'water' out — cluster plan) · mcq4
A ski-jacket fabric is finished with a nonpolar coating. Wet snow slides off the jacket instead of soaking in. What is the molecular reason the coating sheds the moisture?
The coating offers the moisture only weak dispersion attraction, while the moisture's molecules grip one another strongly — so it gathers into drops and slides off. KEY
The nonpolar coating pushes the moisture away with a repelling force.
The coating's molecules would hydrogen-bond onto the wet snow when it first lands, and the constant movement of the skier then shakes those hydrogen bonds loose again.
The coating melts the snow on contact, and the meltwater evaporates before it can soak in.
CMB-059 · medium · application · seq 21 · authored (U5-G3 has zero prod seeds — blueprint directs an authored unlabeled-solids classification FRQ from capstone CMB-059, extending the pool-53 unknown-solid genre; values are real melting points, provenance: F=palmitic acid 63, G=LiCl 605, H=CaF2 1418; instance set disjoint from the lesson's taught set and the placed seeds) · frq
A tray on a lab bench holds three unlabeled crystalline solids, marked only F, G, and H. A technician measures the melting point of each; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
A tray on a lab bench holds three unlabeled crystalline solids, marked only F, G, and H. A technician measures the melting point of each; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
(a) Classify solid G and solid F as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
(b) A classmate says solid F's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
(c) Classify solid H and justify your classification using its melting point.
Part a. Classify solid G and solid F as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
Model: Solid G (melting point 605 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid F (melting point 63 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
Part b. A classmate says solid F's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
Model: Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 63 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
Part c. Classify solid H and justify your classification using its melting point.
Model: Solid H melts at 1418 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
Full model answer. (a) Solid G (melting point 605 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid F (melting point 63 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
(b) Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 63 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
(c) Solid H melts at 1418 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
A chemistry handbook's tables list dispersion forces for every molecular substance — polar and nonpolar alike. Why is that listing correct for all of them?
All molecules attract their neighbors through dispersion forces — no molecule is exempt. KEY
It is not correct — only nonpolar molecules exert dispersion forces.
It is correct only for substances that are liquids or solids, where the molecules touch.
It is correct because every molecular substance's molecules share electrons with their neighbors.
Dipole-dipole attractions act between the molecules of some substances and not others. What must be true of a molecule for it to attract its neighbors this way?
It must be polar, with a permanent δ+ end and a permanent δ− end. KEY
It must contain H atoms somewhere in its structure.
It must be nonpolar, so that its electrons are free to shift.
Any molecule qualifies, because all molecules attract their neighbors.
CMB-042 · easy · application · seq 4 · authored (prefix-swap critique facet, element-free; the inside-the-liquid reading is the taught central trap) · mcq4
A student writes: 'The attraction between two neighboring molecules in a liquid is intramolecular, because it happens inside the liquid.' What is wrong with the classification?
Inside the liquid is not inside a molecule — the attraction acts between two molecules, so it is intermolecular. KEY
Nothing is wrong — any force acting inside a sample of liquid counts as intramolecular.
The classification fails only because liquids have no attractions between their molecules.
The attraction is actually a covalent bond, which needs no inter/intra label.
A sealed flask holds liquid silane, SiH₄, with silane vapor above it. Compare a molecule in the vapor with a molecule in the liquid.
They are identical — the same intact SiH₄ molecules, only farther apart in the vapor. KEY
The vapor molecule is a lighter fragment that escaped from a liquid molecule.
The vapor molecule has lost one of its H atoms, which stays behind in the liquid.
The vapor molecule is chemically different, because gases are a different substance than liquids.
CMB-045 · medium · application · seq 6 · authored (evaporation-transfer facet parallel to form C with a fresh instance; mechanism verbatim in the explanation; ethyl acetate cross-form 3A/15B/5D recorded) · mcq4
As liquid ethyl acetate evaporates from a spill, which attraction is overcome, and which survives?
The attractions between ethyl acetate molecules are overcome; every covalent bond within each molecule survives. KEY
The covalent bonds within each molecule are overcome; the attractions between molecules survive.
Both are overcome — an evaporating molecule leaves as separate atoms.
Neither is overcome — evaporation lifts molecules away without any attraction resisting.
CMB-047 · medium · application · seq 7 · authored (snapshot δ-assignment facet — FLU[2] class with fresh instance N₂ and varied phrasing; N₂ cross-form 4C/16A recorded) · mcq4
A snapshot of one N₂ molecule at a single instant shows its electrons crowded toward one end at that instant. What are the molecule's charges at that moment?
The crowded end is momentarily δ− and the other end momentarily δ+. KEY
The crowded end turns momentarily positive (δ+), leaving the emptied side negative (δ−).
The whole molecule is momentarily negative.
The molecule has split into two oppositely charged ions.
Two similar nonpolar substances are compared, and a student says their dispersion forces must be equally strong 'because neither molecule is polar.' What is the correct comparison?
The substance with larger molecules has the stronger dispersion forces, because larger molecules have more electrons, so the momentary charge imbalances are larger and the attractions stronger. KEY
The student is right — with no permanent charges anywhere, there is nothing left to differ.
The substance with smaller molecules has the stronger dispersion forces, because its electrons sit closer to the nuclei, and closely packed electrons make sharper momentary pile-ups.
The comparison cannot be made without knowing which substance is heavier per liter.
CMB-050 · medium · application · seq 9 · authored (why-facet — FLU[0] class with fresh instance CHCl₃; key = MECH-DIPOLE-DIPOLE verbatim; CHCl₃ cross-form 13A recorded) · mcq4
Chloroform molecules, CHCl₃, are polar, each with a permanent δ+ end and a permanent δ− end. Why do neighboring CHCl₃ molecules attract one another through dipole-dipole attractions?
Because the slightly positive end of one polar molecule attracts the slightly negative end of the next. KEY
Because their moving electrons pile up on one side of each molecule for a brief moment.
Because the δ+ end of one molecule attracts the δ+ end of the next.
Because the molecules pass electrons to one another as they touch.
CMB-051 · medium · application · seq 10 · authored (condition-statement facet; key = rule line 0 verbatim; element words = condition vocabulary, rule-content cluster) · mcq4
Hydrogen bonding forms between molecules only under one condition. Which statement gives it?
An H atom covalently bonded to N, O, or F is attracted to an N, O, or F atom of a neighboring molecule. KEY
Any two polar molecules attract this way, whatever their atoms.
A molecule merely has to contain H and at least one of N, O, or F somewhere, anywhere at all in its structure.
An H atom must break free of its molecule and be shared between the two neighbors.
Part of hydrogen bonding's strength comes from how CLOSE the strongly positive H atom gets to the neighboring molecule's lone pair. What makes that closeness possible?
The H atom is tiny, so it can approach the lone pair very closely. KEY
The lone pair reaches out and covalently bonds to the H atom.
The H atom's heavy nucleus drags it deep into the neighboring molecule.
The two molecules merge briefly, letting the charges touch.
CMB-053 · medium · application · seq 12 · authored (all-three O–H checklist case; fresh instance glycerol — also at 15E, non-adjacent same-form repeat recorded) · mcq4
Glycerol is polar; three of its hydrogens ride on O atoms and the other five ride on C atoms. Which choice lists ALL of the intermolecular forces acting between glycerol molecules?
Dispersion forces, dipole-dipole attractions, and hydrogen bonding KEY
Dispersion forces and dipole-dipole attractions
Dipole-dipole attractions and hydrogen bonding
Dispersion forces only
CMB-053 · medium · application · seq 13 · authored (most-forces tally; glycol third use (10D/13C-foil/13E) recorded — cross-column, non-adjacent; SnCl₄ 13A same-seq? NO — SnCl₄ here is an option on form E while 13A's key is SnCl₄ on form A: same-seq material repeat RECORDED as an A5 watch) · mcq4
Four liquids: ethylene glycol (polar; O–H groups at both ends), SnCl₄ (nonpolar), HI (polar; its only H bonded to I), and SiH₄, silane (nonpolar; Si–H hydrogens). Between which liquid's molecules do the MOST intermolecular forces act?
Ethylene glycol KEY
SnCl₄
HI
Silane, SiH₄
CMB-054 · medium · application · seq 14 · authored (caveat critique; octane vs HI — fresh large-vs-small pair; octane 048-fluency cross-warn recorded) · mcq4
A classmate ranks octane's dispersion forces below HI's dipole-dipole attractions, 'because dipole-dipole always beats dispersion, whatever the molecules.' Octane molecules are far larger than HI molecules. What is wrong with the reasoning?
The ranking holds only for molecules of similar size — a much larger molecule's dispersion forces can outweigh a small molecule's dipole-dipole attractions. KEY
Nothing is wrong — once the force ladder has been established, it applies to every pair of substances, whatever the sizes of their molecules.
The reasoning fails because octane, being nonpolar, has no intermolecular forces to rank.
The reasoning fails because dipole-dipole attractions never beat dispersion forces anywhere.
CMB-055 · medium · application · seq 15 · authored (same-atoms facet parallel to form A with fresh instances — butan-1-ol/diethyl ether are both C₄H₁₀O; butan-1-ol also at 12E, non-adjacent same-form repeat recorded) · mcq4
Butan-1-ol, C₄H₉OH, hydrogen-bonds through its O–H group. Diethyl ether contains exactly the same atoms but has no O–H group, so the strongest attraction its molecules can form is dipole-dipole. Which substance boils at the higher temperature?
Butan-1-ol KEY
Diethyl ether
Both boil at the same temperature, because they contain the same atoms
It cannot be predicted, because the two molecules are the same size
A molecular substance's molecules attract one another only weakly. What does that mean for its boiling point, and why?
A low boiling point — boiling has to pull molecules away from each other, and weak attractions need little energy to overcome. KEY
A high boiling point — weakly attracted molecules rattle around so freely that the liquid needs extra heat before it can boil.
No boiling point at all — a substance with weak attractions is always a gas.
The boiling point depends only on the molecules' size, not on the attractions.
CMB-057 · hard · transfer · seq 17 · authored (weaker-forces read with the negative-scale step; real values NF₃ −129 / PH₃ −88 °C in the figure only; NF₃ 9C / PH₃ 13C/14A/15C cross-form uses recorded) · mcq4
Boiling points for two substances are listed in the table. Which substance has the WEAKER intermolecular forces?
NF₃, because −129 °C is the lower boiling point. KEY
PH₃, because −88 °C is closer to zero.
NF₃, because F atoms always weaken a substance's attractions.
Neither — boiling points this low say nothing about forces.
CMB-059 · hard · transfer · seq 18 · authored (why-gap facet with fresh real pair citric acid 153 / LiBr 552 °C; MECH-LATTICE verbatim; bonds-intact corrective in distractor feedback) · mcq4
Citric acid, a molecular solid, melts at 153 °C. Lithium bromide, an ionic solid, melts at 552 °C. Why does lithium bromide need so much more energy to melt?
Its ions are held in a repeating lattice by attraction between opposite charges acting in every direction; citric acid's molecules are held only by weak attractions. KEY
Melting lithium bromide works by breaking the strong covalent bonds that hold the atoms together inside each one of the molecules that make up its crystal.
Citric acid melts lower because melting it breaks its covalent bonds, which happen to be weak.
Lithium bromide's particles are heavier, and heavier particles always melt higher.
CMB-058 · hard · transfer · seq 19 · authored (bond-claim critique on the anomaly — rule-content cluster; distinct facet from A/B; the intact-molecule corrective is 058's own FLU[2] content) · mcq4
A student says: 'Water boiling at 100 °C proves its O–H covalent bonds are unusually weak — they must snap at just 100 °C.' What is the correct account of water's boiling point?
The O–H bonds do not break at all — 100 °C is where boiling overcomes the hydrogen bonding that links water's molecules, which is unusually strong for a molecule of water's size. KEY
The student is right — a boiling point is exactly the temperature at which a substance's covalent bonds finally give way and its own molecules come apart.
Water's boiling point is actually low for its size, which is why the bonds seem weak.
The O–H bonds break, but they instantly re-form as the steam cools back into water.
CMB-060 · hard · transfer · seq 20 · authored (hold-design case, fresh instance; real anti-fog mechanism; hydrogen-bonding claim respects the N/O/F condition) · mcq4
Anti-fog swim-goggle coatings carry many O–H groups. Instead of fogging into tiny droplets, the moisture inside the goggles spreads into a thin, clear film on the lens. Why does the coating stop the fog?
The O–H groups hold the moisture's molecules by hydrogen bonding, keeping them spread across the lens as a film instead of letting them gather into droplets. KEY
The coating is nonpolar, so it repels the droplets off the lens entirely.
The O–H groups react with the moisture and convert it into a transparent solid.
The coating soaks the moisture down into the body of the lens material itself, where the droplets are hidden and can no longer form a fog.
CMB-059 · medium · application · seq 21 · authored (U5-G3 has zero prod seeds — blueprint directs an authored unlabeled-solids classification FRQ from capstone CMB-059, extending the pool-53 unknown-solid genre; values are real melting points, provenance: R=NaBr 747, S=acetamide 81, T=CaO 2572; instance set disjoint from the lesson's taught set and the placed seeds) · frq
In a supply cupboard sit three unlabeled crystalline solids, marked only R, S, and T. A lab assistant measures each solid's melting point; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
In a supply cupboard sit three unlabeled crystalline solids, marked only R, S, and T. A lab assistant measures each solid's melting point; the results are shown in the table. Every solid is either a molecular solid or an ionic solid.
(a) Classify solid R and solid S as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
(b) A classmate says solid S's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
(c) Classify solid T and justify your classification using its melting point.
Part a. Classify solid R and solid S as molecular or ionic. Justify EACH classification by naming what melting must overcome in that solid.
Model: Solid R (melting point 747 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid S (melting point 81 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
Part b. A classmate says solid S's low melting point proves that its covalent bonds are weak. Explain what is wrong with that claim.
Model: Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 81 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
Part c. Classify solid T and justify your classification using its melting point.
Model: Solid T melts at 2572 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
Full model answer. (a) Solid R (melting point 747 °C) is ionic. A melting point that high means melting must overcome very strong attractions: in an ionic solid the ions are held in a repeating lattice by attraction between opposite charges acting in every direction, and freeing ions from that lattice takes a great deal of energy. Solid S (melting point 81 °C) is molecular. Its low melting point means melting only has to overcome the weak intermolecular attractions between intact molecules, which takes little energy.
(b) Melting a molecular solid never breaks its covalent bonds — the molecules leave the solid intact. What gives way at 81 °C are the much weaker attractions BETWEEN the molecules, so the melting point says nothing about the covalent bonds inside them. Covalent bonds are in fact much stronger than intermolecular forces.
(c) Solid T melts at 2572 °C — far too high for weak between-molecule attractions; it is ionic: its ions are held in a repeating lattice by attraction between opposite charges acting in every direction, so freeing them takes that much energy.
End of Topic Test: Carbon compounds (u05-t4 · 5 forms × 21 items · 105 total)
David's notes for James:
Composition + allocation (confirm): per form 21 items = 17 mcq4 + 2 numeric ENTRY + 1 text ENTRY + 1 FRQ over the 10 scope lessons CMB-061..070 (Unit 5 Topic 12 'Carbon compounds'; D5: min(20, 6 x 10 lessons) = 20 objective + FRQ, full size — matches your target_size 20). The interaction map is YOUR seed design carried through V-T1 slot parity: CMB-065 holds THREE rows (seq 9 text formula-production, seq 10 numeric produce-a-count, seq 11 mcq) because its three gate seeds carry three DIFFERENT interactions and V-T1 fixes interaction per seq; seq 1 is CMB-061's numeric bond-count entry (your produce-a-count seed); CMB-066 holds ONE row (seq 12) hosting its three seeds as rotated cases on forms A/B/C (concept-only fact atom — no group-specific property taught, its three seeds are one concept-application family); capstone CMB-070 = seqs 19 + 20 + the seq-21 FRQ (2-3 cap). Every other lesson has exactly 2 rows. Bands 3 recall / 14 application / 3 transfer, easy -> hard, FRQ terminal.
STRUCTURAL ADJUDICATION — SUBJECT VOCABULARY (THE defining adjudication of this gate; confirm): the gate topic IS carbon compounds, so 'carbon' is rule-line-mandated vocabulary in every scope lesson ('A carbon atom forms four covalent bonds', carbon skeletons, hydrocarbons, ...) and the group-definition lessons cannot avoid 'hydrogen'/'oxygen'/'nitrogen'; V-T7's substance-exclusivity scans are structurally unsatisfiable for the subject nouns — YOUR OWN verbatim seeds fail identically (1,087 of the 2,046 final fail lines touch seed slots). Everything text-fixable WAS content-fixed first (stage-2 sweeps + the 11 genuine-reuse lines at stage 3, all patched, never excused). The residue is excused by SEVEN recorded families in gate_config.json — six material families (SUBJ-CARBON 70 slots / SUBJ-HYDROGEN 11 / SUBJ-OXYGEN 10 / SUBJ-NITROGEN 6 / SUBJ-WATER 6 (CMB-067's taught mixing probe) / SUBJ-AMMONIA 1 (CMB-069's taught NH3 boundary)) + SUBJ-GRAMS (74 ENUMERATED subject-vocabulary grams over 49 slots) — enforced by the gate-local validate_with_adjudications.py wrapper over the UNTOUCHED shared validator (U3-G2/U5-G3 precedent lane): parity-guarded (recomputed fail multiset == printed lines), load-time re-verification that every enumerated gram is subject-vocabulary-only, negative-probed (butane injected -> exit 1 with 3 UNCOVERED lines, restored -> exit 0). Final partition: 2,046/2,046 covered (xf_sub 1,855 / own_mat 73 / adj_mat 44 / inst_gram 38 / spec_gram 27 / xf_gram 9), 0 uncovered. NEW excused kind vs U3-G2 recorded explicitly: WITHIN-FORM ADJACENCY for the subject nouns only (consecutive items about carbon compounds necessarily both say 'carbon'; adjacency screening targets instance telegraphing and the subject noun carries no instance signal). Fresh INSTANCES (specific compounds) remain fully scanned throughout. Flag if you want a different lane — the proposed first-class 'subject_vocabulary' relief key in the shared validator is documented for the maintainer, not applied (wave isolation).
Seed census: pool 30 = 10 lessons x 3 gateItems (verified positionally: 27 byte-exact + 3 notation-transport-only — your pool 0/9/10 carry <sub> markup vs the spec's Unicode); demo_curated 3 = pool 27/28/29 (the CMB-070 capstone trio), dedup'd into the pool with both refs cited. ALL 30 seeds placed (form A 20 / B 9 / C 1 — your curation depth; forms D/E fully authored; 0 spares) -> census 30 seed-carried / 75 authored. Pool difficulty was null throughout — difficulty + band inferred and recorded per seed in seed_placement.json. prod_seeds = [] and the pool holds zero production items -> all five FRQs are OUR authored productions (see the FRQ note).
SEED RULING freshenings (strict — colliding seed instances freshened in content, never validator relief; task, key position and misconception classes verbatim; confirm): B#2 drops the name 'hydrogen cyanide' (the formula H–C≡N kept); A#7 drops the word 'butane' (the C₄H₁₀ formula + straight-vs-branched contrast kept); A#8 'Silicon, in Group 14' -> 'Silicon, directly below carbon in the periodic table' (14 is verbatim spec-corpus text in CMB-062/064; same edit applied at authored D#5/D#8); B#14 ethanol -> hexanol + the hydrogen-count claim de-numbered; A#16's d-option comparison de-instanced ('bigger than vinegar's' -> 'far larger than the frames of the small everyday acids' — YOUR keyExplanation keeps its vinegar citation; feedback fields are scan-exempt); B#12 d-option tail 'only a tiny fraction of it' -> 'only a sliver of the whole' (duplicated CMB-064 article phrasing); B#15 two phrasings freshened where they duplicated your CURATED pool-29 seed at A#20 (the curated side stays byte-verbatim); B#3 'Which statement' -> 'Which claim' (CMB-061 spec 4-gram, caught at stage 3).
NOTA replacements (2 — the opportunistic rule; confirm): pool 7 at A#3: 'None of the above — carbon skeletons cannot combine patterns.' -> 'Two separate molecules — a six-carbon ring and a detached one-carbon piece.' (misconception: disconnecting the drawn C–C bond); pool 17 at C#12: 'None — four carbon compounds always behave alike.' -> 'It cannot be decided from the structures alone — behavior likeness only shows up in lab tests.' (misconception: refusing the structural read the group concept licenses). Pool 5's 'Nothing — ...' option KEPT — it is a substantive no-error claim in the canon register, not a NOTA.
D#8 DISPUTE — the gate's ONE open sol verdict, a RECORDED course-local-authority override; please adjudicate: sol (our authoritative cross-vendor QC) wants D#8's key realigned from the C–C-BOND-STRENGTH claim to carbon's four-bond capacity, and objects that tin replaced the spec's silicon contrast. Our grounds for keeping the strength key: CMB-064's own article setup teaches 'carbon forms four strong covalent bonds' and its extraNotes define the diversity argument as four strong bonds + self-bonding; YOUR gateItems[2] (the A#8 seed, same seq, placed verbatim) keys exactly the strength claim for this element-contrast task; and four-bondedness CANNOT explain a contrast with tin, which is also four-bonded — the discriminating fact is bond strength. Tin is the same-seq freshness rotation of your seed's silicon (V-T7: silicon sits in your A#8 seed). sol's 'untaught' premise is a visibility artifact (its definitions block carries rule lines + specNotes only, not article setup text). Say which way you want it.
Numeric + text ENTRY grading contracts (confirm): seq 1 and seq 10 are integer bond counts — unit 'bonds', sigFigs 1, integer:true, display carried, acceptedAlternates ['<n> bonds']; the seq-1 answer is 4 on EVERY form BY DESIGN (the anchor fact 'a carbon atom forms four covalent bonds' — the case molecule rotates, the answer cannot); seq-10 answers are 5/7/4/6/9 across A–E. Seq 9 is your formula-production task carried verbatim on form A (propene) with fresh rotations B butene C₄H₈ / C dichloromethane CH₂Cl₂ / D fluoroethane C₂H₅F / E pentene C₅H₁₀: canonical Unicode value + the plain-digit alternate (C3H6, ...), graded case-INSENSITIVELY per the gradingNote (C/H/Cl/F create no symbol ambiguity; the caseSensitive flag itself is authoring machinery and is not exported); exported answer.unit/sigFigs are null by the recorded typed-answer convention (U2-G1/U6-G1 lane). Every numeric/text item ships 3 wrongValueDiagnostics (the numeric analogue of mcq misconceptions); internal check self-verification exprs are authoring machinery, not exported.
FRQ design (confirm): prod_seeds is empty, so seq 21 is OUR authored typed functional-group INVENTORY production on capstone CMB-070 — (a) list every functional group with a count (40), (b) justify each identification from the structure and apply the counting rule for O–H clusters inside carboxyl groups (30), (c) predict ONE taught behavior and attribute it to its group (30); rubric sums 100, parts split losslessly; plain-WORD typed answer, no drawing, no formulas needed (V-T12). The molecules rotate the group combos: A 4-aminobutanoic acid (amino + carboxyl), B 2-aminopropan-1-ol (hydroxyl + amino), C 2-hydroxybutanoic acid (hydroxyl + carboxyl), D homoserine (all three), E succinic acid (TWO carboxyls, ZERO hydroxyls — the O–H-inside-carboxyl double-count trap at full strength). Standing typed-plan flag applies.
DELIVERY REQUIREMENT — figures: 44 figure payloads; drawn structures ARE this topic's subject (R10), so rows 3/6/9/10/11/13/19/21 (+ rows 12/15/17 on their panel forms) are answerable ONLY with the structural-formula / carbon-skeleton figure rendered. Confirm your renderer ships both families; skeleton figures carry the canonical 'Hydrogens omitted for clarity.' caption. (Related documented-for-maintainer gap: the shared blind-packet builder had no renderer for these two families — repaired gate-locally for the blind rounds via each figureSpec's positional description; the compound-naming metadata field is never shipped, R23.)
Adjudication ledger beyond the subject family (all instance-free, all recorded in gate_config.json): extra_task_idioms 9 — your four-panel identification template ('The figure shows the structural formulas of four compounds,' — your pool 18/21/24 share it verbatim), CMB-065's production template ('Reading the structure, write'), and the critique-task idioms your correction seeds carry ('The student is right', 'The student's report is correct', 'no correction is needed', 'which correction is right', 'which reply is right', 'the reply should be that', 'What is the correct report?'); extra_convention_phrases 2 — 'a protein building block' (CMB-070's fixed amino-acid descriptor, carried by your curated serine seed) and 'ending in an N bonded to two hydrogens' (the taught amino-pattern description, your pool 25/26). Materials and numbers around the idioms still scan in full.
Blind advisory classes recorded, NOT patched (flag if you want changes): (1) rows 19/20/21 rule-then-apply cueing is YOUR curated design — the A#20 seed states the counting rule immediately before the FRQ (seed-design canon; the dominant cross-item-cue flag class is structural to a one-topic gate whose recall rows restate taught rule lines); (2) A#5/B#5 octet arithmetic ('each bond carbon forms adds one more electron'; methane 4+4=8) is CMB-062's taught rule line — course-local definitions are authority; (3) sol minors on three of your seed distractors (A#5 D1 neat-drawing caricature, A#12 D3 figure-contradicted, A#20 D3 'cancels the whole cluster') recorded as style notes, seeds kept verbatim. The blind rounds' two upheld content defects were both on OUR authored items (E#11 false 'fuel additive' context for 2-butyne; C#8 'short strings' -> 'unbranched strings') — fixed and re-blinded clean.
Instance hygiene (wave-4 binding rule): zero uranium/plutonium/radium/actinide/enrichment/reactor/weapon/radiation-dose framings bank-wide — swept over all 30 seeds at placement and re-swept over the full export at packaging (0 hits). ONE reviewed keep to confirm: your CURATED pool-28 seed at B#19 frames serinol as a building block of X-ray CONTRAST AGENTS — reviewed as NOT a radiation-dose framing (no dose/exposure language; serinol is classroom-safe); kept byte-verbatim. Fresh instances are classroom-safe organics throughout (butene, pentene, dichloromethane, fluoroethane, bromomethane, chloroethene, hexanol, octanol, oxalic/hexanoic/malic/succinic acids, pentylamine, homoserine, 3-aminopropan-1-ol, 6-aminohexanoic acid, ...).
Export mechanics: the shared exporter writes the file in full, then fails its known text-contract assert on the seq-9 typed rows ('numeric contract incomplete' — the numeric unit+sigFigs check applied to text interactions; SEVENTH occurrence after U2-G1/U2-G5/U2-G4/U4-G2/U4-G3/U6-G1/U6-G2, already on the shared maintainer's batch list); the gate-local _verify_james_export.py re-executes the ENTIRE shared verification suite with the interaction-scoping correction plus this gate's recorded contracts — ALL CHECKS PASS, exit 0. One NEW scoping this gate (documented for the maintainer): the shared NOTA scan runs on the whole blob and would flag A#3's seedRef.edits, which is the recorded NOTA-REPLACEMENT ledger quoting your original option text verbatim — the scan is re-run here on student-facing fields (0 hits) plus an exact assert that A#3's seedRef is the only provenance carrier. The other two documented exporter gaps verified NOT to fire here (0 HTML entities; 0 sup/sub markup anywhere — your three <sub>-markup pool items were notation-transported to Unicode at seed mapping, recorded in their seed_ref.edits).
FRQ delivery: your `prod` draw-on-paper class is delivered as a typed diagram-PLAN task (state kinds/recipes/counts/spacing; rubric grades the same observables). Confirm this mapping (pending from the U01-G1 round-trip).
full notes file
# u05-t4 — notes/queries from David's side (U5-G4)
1. Composition + allocation (confirm): per form 21 items = 17 mcq4 + 2 numeric ENTRY + 1 text ENTRY + 1 FRQ over the 10 scope lessons CMB-061..070 (Unit 5 Topic 12 'Carbon compounds'; D5: min(20, 6 x 10 lessons) = 20 objective + FRQ, full size — matches your target_size 20). The interaction map is YOUR seed design carried through V-T1 slot parity: CMB-065 holds THREE rows (seq 9 text formula-production, seq 10 numeric produce-a-count, seq 11 mcq) because its three gate seeds carry three DIFFERENT interactions and V-T1 fixes interaction per seq; seq 1 is CMB-061's numeric bond-count entry (your produce-a-count seed); CMB-066 holds ONE row (seq 12) hosting its three seeds as rotated cases on forms A/B/C (concept-only fact atom — no group-specific property taught, its three seeds are one concept-application family); capstone CMB-070 = seqs 19 + 20 + the seq-21 FRQ (2-3 cap). Every other lesson has exactly 2 rows. Bands 3 recall / 14 application / 3 transfer, easy -> hard, FRQ terminal.
2. STRUCTURAL ADJUDICATION — SUBJECT VOCABULARY (THE defining adjudication of this gate; confirm): the gate topic IS carbon compounds, so 'carbon' is rule-line-mandated vocabulary in every scope lesson ('A carbon atom forms four covalent bonds', carbon skeletons, hydrocarbons, ...) and the group-definition lessons cannot avoid 'hydrogen'/'oxygen'/'nitrogen'; V-T7's substance-exclusivity scans are structurally unsatisfiable for the subject nouns — YOUR OWN verbatim seeds fail identically (1,087 of the 2,046 final fail lines touch seed slots). Everything text-fixable WAS content-fixed first (stage-2 sweeps + the 11 genuine-reuse lines at stage 3, all patched, never excused). The residue is excused by SEVEN recorded families in gate_config.json — six material families (SUBJ-CARBON 70 slots / SUBJ-HYDROGEN 11 / SUBJ-OXYGEN 10 / SUBJ-NITROGEN 6 / SUBJ-WATER 6 (CMB-067's taught mixing probe) / SUBJ-AMMONIA 1 (CMB-069's taught NH3 boundary)) + SUBJ-GRAMS (74 ENUMERATED subject-vocabulary grams over 49 slots) — enforced by the gate-local validate_with_adjudications.py wrapper over the UNTOUCHED shared validator (U3-G2/U5-G3 precedent lane): parity-guarded (recomputed fail multiset == printed lines), load-time re-verification that every enumerated gram is subject-vocabulary-only, negative-probed (butane injected -> exit 1 with 3 UNCOVERED lines, restored -> exit 0). Final partition: 2,046/2,046 covered (xf_sub 1,855 / own_mat 73 / adj_mat 44 / inst_gram 38 / spec_gram 27 / xf_gram 9), 0 uncovered. NEW excused kind vs U3-G2 recorded explicitly: WITHIN-FORM ADJACENCY for the subject nouns only (consecutive items about carbon compounds necessarily both say 'carbon'; adjacency screening targets instance telegraphing and the subject noun carries no instance signal). Fresh INSTANCES (specific compounds) remain fully scanned throughout. Flag if you want a different lane — the proposed first-class 'subject_vocabulary' relief key in the shared validator is documented for the maintainer, not applied (wave isolation).
3. Seed census: pool 30 = 10 lessons x 3 gateItems (verified positionally: 27 byte-exact + 3 notation-transport-only — your pool 0/9/10 carry <sub> markup vs the spec's Unicode); demo_curated 3 = pool 27/28/29 (the CMB-070 capstone trio), dedup'd into the pool with both refs cited. ALL 30 seeds placed (form A 20 / B 9 / C 1 — your curation depth; forms D/E fully authored; 0 spares) -> census 30 seed-carried / 75 authored. Pool difficulty was null throughout — difficulty + band inferred and recorded per seed in seed_placement.json. prod_seeds = [] and the pool holds zero production items -> all five FRQs are OUR authored productions (see the FRQ note).
4. SEED RULING freshenings (strict — colliding seed instances freshened in content, never validator relief; task, key position and misconception classes verbatim; confirm): B#2 drops the name 'hydrogen cyanide' (the formula H–C≡N kept); A#7 drops the word 'butane' (the C₄H₁₀ formula + straight-vs-branched contrast kept); A#8 'Silicon, in Group 14' -> 'Silicon, directly below carbon in the periodic table' (14 is verbatim spec-corpus text in CMB-062/064; same edit applied at authored D#5/D#8); B#14 ethanol -> hexanol + the hydrogen-count claim de-numbered; A#16's d-option comparison de-instanced ('bigger than vinegar's' -> 'far larger than the frames of the small everyday acids' — YOUR keyExplanation keeps its vinegar citation; feedback fields are scan-exempt); B#12 d-option tail 'only a tiny fraction of it' -> 'only a sliver of the whole' (duplicated CMB-064 article phrasing); B#15 two phrasings freshened where they duplicated your CURATED pool-29 seed at A#20 (the curated side stays byte-verbatim); B#3 'Which statement' -> 'Which claim' (CMB-061 spec 4-gram, caught at stage 3).
5. NOTA replacements (2 — the opportunistic rule; confirm): pool 7 at A#3: 'None of the above — carbon skeletons cannot combine patterns.' -> 'Two separate molecules — a six-carbon ring and a detached one-carbon piece.' (misconception: disconnecting the drawn C–C bond); pool 17 at C#12: 'None — four carbon compounds always behave alike.' -> 'It cannot be decided from the structures alone — behavior likeness only shows up in lab tests.' (misconception: refusing the structural read the group concept licenses). Pool 5's 'Nothing — ...' option KEPT — it is a substantive no-error claim in the canon register, not a NOTA.
6. D#8 DISPUTE — the gate's ONE open sol verdict, a RECORDED course-local-authority override; please adjudicate: sol (our authoritative cross-vendor QC) wants D#8's key realigned from the C–C-BOND-STRENGTH claim to carbon's four-bond capacity, and objects that tin replaced the spec's silicon contrast. Our grounds for keeping the strength key: CMB-064's own article setup teaches 'carbon forms four strong covalent bonds' and its extraNotes define the diversity argument as four strong bonds + self-bonding; YOUR gateItems[2] (the A#8 seed, same seq, placed verbatim) keys exactly the strength claim for this element-contrast task; and four-bondedness CANNOT explain a contrast with tin, which is also four-bonded — the discriminating fact is bond strength. Tin is the same-seq freshness rotation of your seed's silicon (V-T7: silicon sits in your A#8 seed). sol's 'untaught' premise is a visibility artifact (its definitions block carries rule lines + specNotes only, not article setup text). Say which way you want it.
7. Numeric + text ENTRY grading contracts (confirm): seq 1 and seq 10 are integer bond counts — unit 'bonds', sigFigs 1, integer:true, display carried, acceptedAlternates ['<n> bonds']; the seq-1 answer is 4 on EVERY form BY DESIGN (the anchor fact 'a carbon atom forms four covalent bonds' — the case molecule rotates, the answer cannot); seq-10 answers are 5/7/4/6/9 across A–E. Seq 9 is your formula-production task carried verbatim on form A (propene) with fresh rotations B butene C₄H₈ / C dichloromethane CH₂Cl₂ / D fluoroethane C₂H₅F / E pentene C₅H₁₀: canonical Unicode value + the plain-digit alternate (C3H6, ...), graded case-INSENSITIVELY per the gradingNote (C/H/Cl/F create no symbol ambiguity; the caseSensitive flag itself is authoring machinery and is not exported); exported answer.unit/sigFigs are null by the recorded typed-answer convention (U2-G1/U6-G1 lane). Every numeric/text item ships 3 wrongValueDiagnostics (the numeric analogue of mcq misconceptions); internal check self-verification exprs are authoring machinery, not exported.
8. FRQ design (confirm): prod_seeds is empty, so seq 21 is OUR authored typed functional-group INVENTORY production on capstone CMB-070 — (a) list every functional group with a count (40), (b) justify each identification from the structure and apply the counting rule for O–H clusters inside carboxyl groups (30), (c) predict ONE taught behavior and attribute it to its group (30); rubric sums 100, parts split losslessly; plain-WORD typed answer, no drawing, no formulas needed (V-T12). The molecules rotate the group combos: A 4-aminobutanoic acid (amino + carboxyl), B 2-aminopropan-1-ol (hydroxyl + amino), C 2-hydroxybutanoic acid (hydroxyl + carboxyl), D homoserine (all three), E succinic acid (TWO carboxyls, ZERO hydroxyls — the O–H-inside-carboxyl double-count trap at full strength). Standing typed-plan flag applies.
9. DELIVERY REQUIREMENT — figures: 44 figure payloads; drawn structures ARE this topic's subject (R10), so rows 3/6/9/10/11/13/19/21 (+ rows 12/15/17 on their panel forms) are answerable ONLY with the structural-formula / carbon-skeleton figure rendered. Confirm your renderer ships both families; skeleton figures carry the canonical 'Hydrogens omitted for clarity.' caption. (Related documented-for-maintainer gap: the shared blind-packet builder had no renderer for these two families — repaired gate-locally for the blind rounds via each figureSpec's positional description; the compound-naming metadata field is never shipped, R23.)
10. Adjudication ledger beyond the subject family (all instance-free, all recorded in gate_config.json): extra_task_idioms 9 — your four-panel identification template ('The figure shows the structural formulas of four compounds,' — your pool 18/21/24 share it verbatim), CMB-065's production template ('Reading the structure, write'), and the critique-task idioms your correction seeds carry ('The student is right', 'The student's report is correct', 'no correction is needed', 'which correction is right', 'which reply is right', 'the reply should be that', 'What is the correct report?'); extra_convention_phrases 2 — 'a protein building block' (CMB-070's fixed amino-acid descriptor, carried by your curated serine seed) and 'ending in an N bonded to two hydrogens' (the taught amino-pattern description, your pool 25/26). Materials and numbers around the idioms still scan in full.
11. Blind advisory classes recorded, NOT patched (flag if you want changes): (1) rows 19/20/21 rule-then-apply cueing is YOUR curated design — the A#20 seed states the counting rule immediately before the FRQ (seed-design canon; the dominant cross-item-cue flag class is structural to a one-topic gate whose recall rows restate taught rule lines); (2) A#5/B#5 octet arithmetic ('each bond carbon forms adds one more electron'; methane 4+4=8) is CMB-062's taught rule line — course-local definitions are authority; (3) sol minors on three of your seed distractors (A#5 D1 neat-drawing caricature, A#12 D3 figure-contradicted, A#20 D3 'cancels the whole cluster') recorded as style notes, seeds kept verbatim. The blind rounds' two upheld content defects were both on OUR authored items (E#11 false 'fuel additive' context for 2-butyne; C#8 'short strings' -> 'unbranched strings') — fixed and re-blinded clean.
12. Instance hygiene (wave-4 binding rule): zero uranium/plutonium/radium/actinide/enrichment/reactor/weapon/radiation-dose framings bank-wide — swept over all 30 seeds at placement and re-swept over the full export at packaging (0 hits). ONE reviewed keep to confirm: your CURATED pool-28 seed at B#19 frames serinol as a building block of X-ray CONTRAST AGENTS — reviewed as NOT a radiation-dose framing (no dose/exposure language; serinol is classroom-safe); kept byte-verbatim. Fresh instances are classroom-safe organics throughout (butene, pentene, dichloromethane, fluoroethane, bromomethane, chloroethene, hexanol, octanol, oxalic/hexanoic/malic/succinic acids, pentylamine, homoserine, 3-aminopropan-1-ol, 6-aminohexanoic acid, ...).
13. Export mechanics: the shared exporter writes the file in full, then fails its known text-contract assert on the seq-9 typed rows ('numeric contract incomplete' — the numeric unit+sigFigs check applied to text interactions; SEVENTH occurrence after U2-G1/U2-G5/U2-G4/U4-G2/U4-G3/U6-G1/U6-G2, already on the shared maintainer's batch list); the gate-local _verify_james_export.py re-executes the ENTIRE shared verification suite with the interaction-scoping correction plus this gate's recorded contracts — ALL CHECKS PASS, exit 0. One NEW scoping this gate (documented for the maintainer): the shared NOTA scan runs on the whole blob and would flag A#3's seedRef.edits, which is the recorded NOTA-REPLACEMENT ledger quoting your original option text verbatim — the scan is re-run here on student-facing fields (0 hits) plus an exact assert that A#3's seedRef is the only provenance carrier. The other two documented exporter gaps verified NOT to fire here (0 HTML entities; 0 sup/sub markup anywhere — your three <sub>-markup pool items were notation-transported to Unicode at seed mapping, recorded in their seed_ref.edits).
In ethane, H₃C–CH₃, each carbon is bonded to three hydrogens and to the other carbon. How many covalent bonds does EACH carbon atom form?
Answer: 4 bonds KEY
also accepted: 4 bonds
wrongValueDiagnostics
[
{
"value": 3,
"misconception": "you counted only the hydrogens — the C–C bond belongs to each carbon's count as well",
"feedback": null
},
{
"value": 7,
"misconception": "you added both carbons' bonds together — the question asks for the count at EACH carbon, which is four",
"feedback": null
},
{
"value": 8,
"misconception": "you counted every atom in the molecule — the count is the bonds at one carbon: three to H plus one to C",
"feedback": null
}
]
feedback
{
"keyExplanation": "A carbon atom forms four covalent bonds. Each carbon in ethane has three bonds to hydrogen atoms and one bond to the other carbon: 3 + 1 = 4."
}
Four students each draw a carbon atom in a molecule. Whose carbon is drawn with the correct number of bonds?
The student whose carbon has two single bonds and one double bond. KEY
The student whose carbon has three single bonds and nothing else.
The student whose carbon has two double bonds and one single bond.
The student whose carbon has one triple bond and nothing else.
CMB-063 · easy · recall · seq 3 · seed:U5-G4/pool[7] (= CMB-063 gateItems[1], James) — NOTA distractor REPLACED with a substantive misconception-keyed one (opportunistic rule, ANSWERS #2; recorded in seed_placement.json) · mcq4
The figure shows the carbon skeleton of a molecule found in gasoline. What kind of skeleton is it?
FIGURE (carbon-skeleton · stimulus) — description: "seven carbon atoms: six joined by single bonds into a closed hexagon, with a seventh carbon bonded to one of the ring carbons" · caption: "Hydrogens omitted for clarity." · style: "clean skeleton diagram matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "seven carbon atoms: six joined by single bonds into a closed hexagon, with a seventh carbon bonded to one of the ring carbons",
"caption": "Hydrogens omitted for clarity.",
"style": "clean skeleton diagram matching the lesson figure's layout"
}
}
A ring, with one extra carbon attached to it. KEY
A straight chain of seven carbons.
A branched chain with no ring anywhere.
Two separate molecules — a six-carbon ring and a detached one-carbon piece.
The figure shows the carbon skeletons of two molecules, P and Q. Which description is correct?
FIGURE (carbon-skeleton · stimulus) — description: "two skeletons side by side: P is eight carbon atoms joined in one unbranched row; Q is five carbon atoms with a central carbon bonded to the other four" · caption: "Hydrogens omitted for clarity." · style: "clean two-skeleton comparison panel matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "two skeletons side by side: P is eight carbon atoms joined in one unbranched row; Q is five carbon atoms with a central carbon bonded to the other four",
"caption": "Hydrogens omitted for clarity.",
"style": "clean two-skeleton comparison panel matching the lesson figure's layout"
}
}
P is a straight chain and Q is a branched chain. KEY
P is a branched chain and Q is a straight chain.
P is a straight chain and Q is a ring.
Both are straight chains of different lengths.
CMB-064 · medium · application · seq 7 · seed:U5-G4/pool[9] (= CMB-064 gateItems[0], James) — compound NAME dropped from the stem at placement (the C₄H₁₀ formula and the straight-vs-branched contrast kept): 'butane' is a base-lexicon material and a CMB-064 corpus word (strict SEED RULING; recorded in seed_placement.json) · mcq4
A student compares the two C₄H₁₀ skeletons — a straight chain and a branched chain — and says: 'Same formula, so they are the same compound drawn two ways.' Which correction is right?
They are two different compounds — every different arrangement of the same atoms is a different compound, and the two have different properties. KEY
The student is right — two structures with the same molecular formula are always one and the same compound, just drawn from two different angles on the page.
They are the same compound, but only at the same temperature.
They are different compounds only if they also have different formulas.
CMB-064 · medium · application · seq 8 · seed:U5-G4/pool[11] (= CMB-064 gateItems[2], James) — 'in Group 14' dropped from the stem at placement per the strict SEED RULING: the number 14 is spec-corpus text in CMB-062 ('Carbon sits in Group 14' rule line) and CMB-064, a V-T7 spec-number FAIL class; 'directly below carbon' carries the same position fact · mcq4
Silicon, directly below carbon in the periodic table, also forms four bonds — yet silicon builds nowhere near carbon's tens of millions of compounds. Which additional carbon fact does the most work in the diversity argument?
Carbon's bonds to other carbons are strong, so long chains, branches, and rings hold together. KEY
Carbon atoms are much lighter than silicon atoms, and lighter atoms always make more compounds.
Carbon can form five bonds when it needs to, giving it extra options.
Carbon compounds are all found in living things, which produce them in great variety.
CMB-065 · medium · application · seq 9 · seed:U5-G4/pool[12] (= CMB-065 gateItems[0], James) — verbatim (field mapping only; explanation_incorrect recast into feedback.anticipatedWrong; James's plain-digit alternate C3H6 carried) · text
The figure shows the structural formula of propene. Reading the structure, write the molecular formula of propene.
FIGURE (structural-formula · stimulus) — description: "three C symbols in a row: the first and second carbons joined by two parallel lines (a double bond), the second and third joined by a single line; the first… · molecule: "propene" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "three C symbols in a row: the first and second carbons joined by two parallel lines (a double bond), the second and third joined by a single line; the first carbon bonded to two H symbols, the second to one H, the third to three H",
"molecule": "propene",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: C₃H₆ KEY
also accepted: C3H6
wrongValueDiagnostics
[
{
"value": "C₃H₈",
"misconception": "you gave the double-bonded carbons a full set of hydrogens — the double bond uses two of each carbon's four lines, leaving fewer for hydrogen: the count is 2 + 1 + 3 = 6",
"feedback": "This answer is wrong — you gave the double-bonded carbons a full set of hydrogens — the double bond uses two of each carbon's four lines, leaving fewer for hydrogen: the count is 2 + 1 + 3 = 6."
},
{
"value": "C₄H₆",
"misconception": "you counted the double bond as an extra carbon — two parallel lines are one double bond between the SAME two carbons",
"feedback": "This answer is wrong — you counted the double bond as an extra carbon — two parallel lines are one double bond between the SAME two carbons."
},
{
"value": "C₃H₃",
"misconception": "you dropped the CH₃ end's hydrogens — the third carbon carries three: 2 + 1 + 3 = 6",
"feedback": "This answer is wrong — you dropped the CH₃ end's hydrogens — the third carbon carries three: 2 + 1 + 3 = 6."
}
]
feedback
{
"keyExplanation": "Count the atoms from the structure: three carbons, and hydrogens 2 + 1 + 3 = 6, so propene is C₃H₆. The two parallel lines are one C=C double bond — two shared pairs — which is why those carbons carry fewer hydrogens than a fully single-bonded chain.",
"anticipatedWrong": [
{
"value": "C₃H₈",
"misconception": "you gave the double-bonded carbons a full set of hydrogens — the double bond uses two of each carbon's four lines, leaving fewer for hydrogen: the count is 2 + 1 + 3 = 6",
"feedback": "This answer is wrong — you gave the double-bonded carbons a full set of hydrogens — the double bond uses two of each carbon's four lines, leaving fewer for hydrogen: the count is 2 + 1 + 3 = 6."
},
{
"value": "C₄H₆",
"misconception": "you counted the double bond as an extra carbon — two parallel lines are one double bond between the SAME two carbons",
"feedback": "This answer is wrong — you counted the double bond as an extra carbon — two parallel lines are one double bond between the SAME two carbons."
},
{
"value": "C₃H₃",
"misconception": "you dropped the CH₃ end's hydrogens — the third carbon carries three: 2 + 1 + 3 = 6",
"feedback": "This answer is wrong — you dropped the CH₃ end's hydrogens — the third carbon carries three: 2 + 1 + 3 = 6."
}
]
}
CMB-065 · medium · application · seq 10 · seed:U5-G4/pool[13] (= CMB-065 gateItems[1], James) — verbatim (field mapping only; explanation_incorrect recast into the misconceptions list) · numeric
The figure shows the structural formula of chloroethane. How many C–H bonds does the structure contain?
FIGURE (structural-formula · stimulus) — description: "two C symbols joined by a single line; the first carbon bonded to three H symbols, the second carbon bonded to two H symbols and one Cl symbol" · molecule: "chloroethane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "two C symbols joined by a single line; the first carbon bonded to three H symbols, the second carbon bonded to two H symbols and one Cl symbol",
"molecule": "chloroethane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: 5 bonds KEY
also accepted: 5 bonds
wrongValueDiagnostics
[
{
"value": 7,
"misconception": "you counted every bond in the molecule — the question asks for C–H bonds only, and the C–C and C–Cl lines are not C–H bonds",
"feedback": null
},
{
"value": 6,
"misconception": "you counted the C–Cl bond as a C–H bond — chlorine is not hydrogen: the C–H count is 3 + 2 = 5",
"feedback": null
},
{
"value": 3,
"misconception": "you counted only one carbon's hydrogens — both carbons carry hydrogens: 3 on one, 2 on the other",
"feedback": null
}
]
feedback
{
"keyExplanation": "Trace each line from a carbon to an H symbol: the first carbon has three C–H bonds and the second has two, so the structure contains 3 + 2 = 5 C–H bonds. The C–C line and the C–Cl line are bonds too, but not C–H bonds."
}
The figure shows the structural formula of a molecule used in welding fuel research. Which full reading of the structure is correct?
FIGURE (structural-formula · stimulus) — molecule: "propyne" · description: "three C symbols in a row: the first and second carbons joined by three parallel lines (a triple bond), the second and third joined by a single line; the fir… · style: "clean full structural formula matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "propyne",
"description": "three C symbols in a row: the first and second carbons joined by three parallel lines (a triple bond), the second and third joined by a single line; the first carbon bonded to one H symbol, the third carbon bonded to three H symbols",
"style": "clean full structural formula matching the lesson figure's layout"
}
}
C₃H₄, containing one triple bond, one C–C single bond, and four C–H bonds. KEY
C₃H₄, containing three separate C–C single bonds between the first two carbons.
C₃H₈, with every carbon carrying a full set of hydrogens.
C₂H₄, because the middle carbon only bridges the other two.
The figure shows a six-carbon compound with a small two-atom cluster attached to one end. A chemist predicts the compound's behavior by looking only at the small cluster. Why is that shortcut justified?
FIGURE (structural-formula · stimulus) — molecule: "generic six-carbon compound" · description: "a six-carbon chain drawn in full with its hydrogens, carrying a two-atom cluster (drawn as two joined generic atom circles labeled 'small attached cluster')… · style: "clean structural formula with the attached cluster boxed, matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "generic six-carbon compound",
"description": "a six-carbon chain drawn in full with its hydrogens, carrying a two-atom cluster (drawn as two joined generic atom circles labeled 'small attached cluster') on the end carbon; the cluster is boxed",
"style": "clean structural formula with the attached cluster boxed, matching the lesson figure's layout"
}
}
A functional group gives a carbon compound its characteristic properties, so the small cluster is where the behavior comes from. KEY
The shortcut is not justified — a compound's behavior always comes from the longest carbon chain in its skeleton, not from anything attached to it.
Small clusters are easier to see, so chemists study them first for convenience.
The cluster is the only part of the molecule that contains covalent bonds.
The figure shows the structural formulas of four compounds, W, X, Y, and Z. Which compound contains a hydroxyl group?
FIGURE (structural-formula · stimulus) — molecule: "four-compound comparison" · description: "four small structures in a row: W is a five-carbon chain with only C–H and C–C bonds; X is a five-carbon chain whose end carbon is bonded to an O, which is … · style: "clean four-panel structural formula comparison labeled W to Z, matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "four-compound comparison",
"description": "four small structures in a row: W is a five-carbon chain with only C–H and C–C bonds; X is a five-carbon chain whose end carbon is bonded to an O, which is bonded to an H; Y is a five-carbon chain whose end carbon is bonded to a Cl; Z is a five-carbon chain with a C=C double bond and only hydrogens attached",
"style": "clean four-panel structural formula comparison labeled W to Z, matching the lesson figure's layout"
}
}
Pentane and pentanol are both five-carbon compounds, but pentanol's structure carries an –OH on its end carbon. Which compound should mix better with water, and why?
Pentanol, because its hydroxyl group hydrogen-bonds to water molecules. KEY
Pentane, because a bare carbon frame slips between water molecules more easily.
Both equally, because their carbon frames are the same length.
Pentanol, because the oxygen atom makes it heavier, and heavier liquids absorb water.
The figure shows the structural formulas of four compounds, J, K, L, and M. Which compound contains a carboxyl group?
FIGURE (structural-formula · stimulus) — molecule: "four-compound comparison" · description: "four small structures in a row: J is a three-carbon chain whose end carbon is bonded to an O–H only; K is a three-carbon chain whose end carbon carries a do… · style: "clean four-panel structural formula comparison labeled J to M, matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "four-compound comparison",
"description": "four small structures in a row: J is a three-carbon chain whose end carbon is bonded to an O–H only; K is a three-carbon chain whose end carbon carries a double-bonded O and an O–H together; L is a three-carbon chain whose middle carbon carries a double-bonded O only, with no O–H anywhere; M is a plain three-carbon chain with only C–H and C–C bonds",
"style": "clean four-panel structural formula comparison labeled J to M, matching the lesson figure's layout"
}
}
K KEY
J
L
M
CMB-068 · medium · application · seq 16 · seed:U5-G4/pool[23] (= CMB-068 gateItems[2], James) — d-option FRESHENED at placement per the strict SEED RULING ('vinegar' is CMB-068's article instance and a base-lexicon material): frame-comparison wording made instance-free; misconception (frame vetoes group) kept; all other text verbatim · mcq4
Lemon-fresh cleaning sprays advertise citric acid, whose molecules carry –COOH clusters. Which prediction about the compound follows from its structure?
It is acidic, because the carboxyl group makes a compound acidic. KEY
It is basic, because oxygen-rich groups are always basic.
It is acidic, but only when the spray is heated.
Nothing can be predicted, because citric acid's frame is far larger than the frames of the small everyday acids.
The figure shows the structural formulas of four compounds, E, F, G, and H. Which compound contains an amino group?
FIGURE (structural-formula · stimulus) — molecule: "four-compound comparison" · description: "four small structures in a row: E is a three-carbon chain whose end carbon is bonded to an O–H; F is a three-carbon chain whose end carbon carries a double-… · style: "clean four-panel structural formula comparison labeled E to H, matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "four-compound comparison",
"description": "four small structures in a row: E is a three-carbon chain whose end carbon is bonded to an O–H; F is a three-carbon chain whose end carbon carries a double-bonded O and an O–H; G is a three-carbon chain whose end carbon is bonded to an N with two hydrogens; H is a plain three-carbon chain with only C–H and C–C bonds",
"style": "clean four-panel structural formula comparison labeled E to H, matching the lesson figure's layout"
}
}
A lab note says compound Q 'neutralizes the sourness of an acidic spill'. Q's structure is a two-carbon frame ending in an N bonded to two hydrogens. Which statement explains why Q's structure gives it this acid-neutralizing behavior?
Q's amino group makes it basic — the chemical opposite of acidic — so it counteracts the acidic spill. KEY
Q's amino group makes it acidic just like the spill, so adding it would double the spill's sourness instead of neutralizing it.
Q works because its carbon frame absorbs the spill like a sponge.
Q works only if it also carries a carboxyl group somewhere.
The figure shows the structural formula of serine, a protein building block. Which functional groups does the molecule carry?
FIGURE (structural-formula · stimulus) — molecule: "serine" · description: "a three-carbon structure: the first carbon bonded to two hydrogens and an O–H; the second (central) carbon bonded to one hydrogen and an N with two hydrogen… · style: "clean full structural formula matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "serine",
"description": "a three-carbon structure: the first carbon bonded to two hydrogens and an O–H; the second (central) carbon bonded to one hydrogen and an N with two hydrogens; the third carbon carrying a double-bonded O and an O–H",
"style": "clean full structural formula matching the lesson figure's layout"
}
}
One hydroxyl group, one amino group, and one carboxyl group KEY
One amino group, one carboxyl group, and no hydroxyl group
Two hydroxyl groups, one amino group, and no carboxyl group
One hydroxyl group, two amino groups, and no carboxyl group
A student reads the structural formula of an acid whose end carbon carries a double-bonded O and an O–H, and whose other carbons carry only hydrogens. The student reports: 'one carboxyl group AND one hydroxyl group, because I can see an O–H.' What is the correct report?
One carboxyl group only — the O–H the student saw is inside the carboxyl group and is not counted again as a hydroxyl. KEY
The student's report is correct — every O–H anywhere in any structure always counts as its own separate hydroxyl group.
One hydroxyl group only — a carboxyl group needs a nitrogen atom to complete it.
No groups at all — an O–H inside another cluster cancels the whole cluster.
CMB-070 · medium · application · seq 21 · authored — UNSEEDED FRQ (prod_seeds = []); R14 written production per the blueprint seq-21 case; typed answer is plain words (V-T12: nothing typed requires sub/superscripts) · frq
The figure shows the structural formula of a compound the body makes to calm nerve signaling.
FIGURE (structural-formula · stimulus) — description: "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second and third carbons each bonded to two hydrogens; the fourth carbon bo… · molecule: "4-aminobutanoic acid" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second and third carbons each bonded to two hydrogens; the fourth carbon bonded to two hydrogens and an N with two hydrogens",
"molecule": "4-aminobutanoic acid",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
The figure shows the structural formula of a compound the body makes to calm nerve signaling.
(a) List every functional group the molecule carries, with a count for each group.
(b) Justify each identification from the structure — say what is bonded to what — and state whether the O–H on the first carbon adds a separate hydroxyl group, and why.
(c) Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Part a. List every functional group the molecule carries, with a count for each group.
Model: The molecule carries two functional groups: one carboxyl group and one amino group.
Part b. Justify each identification from the structure — say what is bonded to what — and state whether the O–H on the first carbon adds a separate hydroxyl group, and why.
Model: The first carbon carries a double-bonded O together with an O–H — that pairing on one carbon is the carboxyl pattern. The end carbon carries an N bonded to two hydrogens — the amino pattern. The O–H does NOT add a separate hydroxyl group: it sits on the double-bonded-O carbon, so it is counted inside the carboxyl.
Part c. Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Model: The carboxyl group makes the compound acidic. (Also acceptable: the amino group makes it basic.)
Full model answer. (a) The molecule carries two functional groups: one carboxyl group and one amino group.
(b) The first carbon carries a double-bonded O together with an O–H — that pairing on one carbon is the carboxyl pattern. The end carbon carries an N bonded to two hydrogens — the amino pattern. The O–H does NOT add a separate hydroxyl group: it sits on the double-bonded-O carbon, so it is counted inside the carboxyl.
(c) The carboxyl group makes the compound acidic. (Also acceptable: the amino group makes it basic.)
A carbon atom in a molecule is bonded to two hydrogens and joined to a neighboring carbon by a double bond. How many covalent bonds is that carbon forming?
Answer: 4 bonds KEY
also accepted: 4 bonds
wrongValueDiagnostics
[
{
"value": 3,
"misconception": "you counted the double bond as one — it counts as two of the carbon's bonds: 2 + 2 = 4",
"feedback": null
},
{
"value": 2,
"misconception": "you counted only the hydrogens — the double bond to the neighboring carbon adds two more: 2 + 2 = 4",
"feedback": null
},
{
"value": 6,
"misconception": "you doubled everything — only the double bond counts twice: 2 + 2 = 4",
"feedback": null
}
]
feedback
{
"keyExplanation": "Count lines, not neighbors. Two single bonds to hydrogens count 2, and a double bond counts as two more: 2 + 2 = 4 — a carbon atom forms four covalent bonds."
}
CMB-061 · easy · recall · seq 2 · seed:U5-G4/pool[1] (= CMB-061 gateItems[1], James) — molecule NAME dropped from the stem at placement (formula H–C≡N kept): 'hydrogen' is a base-lexicon material inside CMB-061's own article vocabulary (strict SEED RULING; recorded in seed_placement.json) · mcq4
In the molecule H–C≡N, a student says the carbon forms only two bonds 'because it touches only two atoms.' How many bonds does the carbon actually form?
Four — the single bond to H counts as one and the triple bond to N counts as three. KEY
Two — one to each neighboring atom.
Three — the triple bond alone.
Five — one to the H, three to the N, and one more bond for the lone pair on the carbon.
The figure shows the carbon skeletons of two molecules, R and S. Which description is correct?
FIGURE (carbon-skeleton · stimulus) — description: "two skeletons side by side: R is six carbon atoms, five joined in a row with the sixth bonded to the second carbon of the row; S is six carbon atoms joined … · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "two skeletons side by side: R is six carbon atoms, five joined in a row with the sixth bonded to the second carbon of the row; S is six carbon atoms joined into one closed hexagon",
"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
R is a branched chain and S is a ring. KEY
R is a ring and S is a branched chain.
R is a straight chain and S is a ring.
Both are branched chains of different sizes.
CMB-064 · medium · application · seq 7 · seed:U5-G4/pool[10] (= CMB-064 gateItems[1], James) — verbatim (field mapping only; the C₇H₁₆ formula is gate-item-only vocabulary — the fluency corpus formula is C₆H₁₄, checked at stage 1) · mcq4
C₇H₁₆ can be assembled onto nine different skeletons, while C₄H₁₀ allows only two. What does the comparison show about carbon compounds?
The number of possible arrangements grows quickly as carbons are added, which is why carbon compounds are so numerous. KEY
Larger formulas are more stable, so nature keeps more of them.
Only formulas with an odd number of carbon atoms allow many different arrangements, and C₇H₁₆ qualifies while C₄H₁₀ does not.
The nine arrangements of C₇H₁₆ are nine samples of one compound.
CMB-064 · medium · application · seq 8 · authored (which-facts audit, parallel to seed pool[11]'s argument-anatomy class) · mcq4
A textbook argument runs: 'Carbon builds tens of millions of compounds.' Which PAIR of carbon facts does the argument actually need?
Carbon's four bonds are spendable on other carbons, and each different skeleton from the same atoms is a new compound. KEY
Carbon forms four bonds, and its atoms are light, so more of them fit into every batch of compounds.
Carbon bonds readily to hydrogen, and the hydrogens supply the extra bonds that let skeletons grow.
Carbon forms four bonds, and it can stretch to five when a skeleton gets crowded.
CMB-065 · medium · application · seq 9 · authored (formula production, parallel to seed pool[12]; fresh mid-chain double-bond structure, name kept as a figure label only per the CMB-065 specNote) · text
The figure shows the structural formula of a fuel-lab sample. From the structure, write its molecular formula.
FIGURE (structural-formula · stimulus) — description: "four C symbols in a row: the second and third carbons joined by two parallel lines (a double bond), the other links single lines; the first and fourth carbo… · molecule: "butene (mid-chain double bond)" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four C symbols in a row: the second and third carbons joined by two parallel lines (a double bond), the other links single lines; the first and fourth carbons each bonded to three H symbols, the second and third each bonded to one H",
"molecule": "butene (mid-chain double bond)",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: C₄H₈ KEY
also accepted: C4H8
wrongValueDiagnostics
[
{
"value": "C₄H₁₀",
"misconception": "you gave the double-bonded carbons full sets of hydrogens — the double bond uses two of each middle carbon's four lines: the count is 3 + 1 + 1 + 3 = 8",
"feedback": "This answer is wrong — you gave the double-bonded carbons full sets of hydrogens — the double bond uses two of each middle carbon's four lines: the count is 3 + 1 + 1 + 3 = 8."
},
{
"value": "C₅H₈",
"misconception": "you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons",
"feedback": "This answer is wrong — you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons."
},
{
"value": "C₄H₆",
"misconception": "you shorted the end carbons — each end carbon carries three hydrogens: 3 + 1 + 1 + 3 = 8",
"feedback": "This answer is wrong — you shorted the end carbons — each end carbon carries three hydrogens: 3 + 1 + 1 + 3 = 8."
}
]
feedback
{
"keyExplanation": "Count the atoms: four carbons, and hydrogens 3 + 1 + 1 + 3 = 8, so the formula is C₄H₈. The two parallel lines between the middle carbons are one double bond, which is why those two carry one hydrogen each.",
"anticipatedWrong": [
{
"value": "C₄H₁₀",
"misconception": "you gave the double-bonded carbons full sets of hydrogens — the double bond uses two of each middle carbon's four lines: the count is 3 + 1 + 1 + 3 = 8",
"feedback": "This answer is wrong — you gave the double-bonded carbons full sets of hydrogens — the double bond uses two of each middle carbon's four lines: the count is 3 + 1 + 1 + 3 = 8."
},
{
"value": "C₅H₈",
"misconception": "you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons",
"feedback": "This answer is wrong — you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons."
},
{
"value": "C₄H₆",
"misconception": "you shorted the end carbons — each end carbon carries three hydrogens: 3 + 1 + 1 + 3 = 8",
"feedback": "This answer is wrong — you shorted the end carbons — each end carbon carries three hydrogens: 3 + 1 + 1 + 3 = 8."
}
]
}
The figure shows a compound's structural formula. How many C–H bonds does the structure contain?
FIGURE (structural-formula · stimulus) — description: "three C symbols joined in a row by single lines; the first carbon bonded to three H symbols, the second to two H symbols, the third to two H symbols and one… · molecule: "chloropropane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "three C symbols joined in a row by single lines; the first carbon bonded to three H symbols, the second to two H symbols, the third to two H symbols and one Cl symbol",
"molecule": "chloropropane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: 7 bonds KEY
also accepted: 7 bonds
wrongValueDiagnostics
[
{
"value": 10,
"misconception": "you counted every bond in the molecule — the two C–C lines and the C–Cl line are not C–H bonds",
"feedback": null
},
{
"value": 8,
"misconception": "you counted the C–Cl bond as a C–H bond — chlorine is not hydrogen: the count is 3 + 2 + 2 = 7",
"feedback": null
},
{
"value": 3,
"misconception": "you counted only the first carbon's hydrogens — all three carbons carry hydrogens",
"feedback": null
}
]
feedback
{
"keyExplanation": "Trace each line from a carbon to an H symbol: 3 on the first carbon, 2 on the second, and 2 on the third give 3 + 2 + 2 = 7 C–H bonds. The C–C and C–Cl lines are bonds, but not C–H bonds."
}
The figure shows the structural formula of a molecule used in making a common plastic. Which full reading of the structure is correct?
FIGURE (structural-formula · stimulus) — description: "two C symbols joined by two parallel lines (a double bond); the first carbon bonded to two H symbols, the second bonded to one H symbol and one Cl symbol" · molecule: "chloroethene" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "two C symbols joined by two parallel lines (a double bond); the first carbon bonded to two H symbols, the second bonded to one H symbol and one Cl symbol",
"molecule": "chloroethene",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
C₂H₃Cl, containing one C=C double bond, three C–H bonds, and one C–Cl bond. KEY
C₂H₃Cl, containing two separate C–C single bonds between the two carbons.
C₂H₅Cl, with both carbons carrying full sets of hydrogens.
C₃H₃Cl, counting the double bond as an extra carbon.
CMB-066 · medium · application · seq 12 · seed:U5-G4/pool[16] (= CMB-066 gateItems[1], James) — one distractor TAIL freshened at placement per the strict SEED RULING: 'only a tiny fraction of it' duplicates CMB-064 article phrasing (V-T7 spec-gram class); misconception and claim structure verbatim · mcq4
A student says: 'Adding one small group of atoms to a carbon compound can't change much — the compound is mostly unchanged carbon frame.' Which reply is correct?
A functional group, small as it is, gives the compound its characteristic properties — a stove fuel becomes hand-sanitizer liquid by gaining one –OH. KEY
The student is right — a compound's properties change only in proportion to how much of its molecule changes, and one small group is only a sliver of the whole.
The student is right for small molecules but wrong for large ones.
The reply should be that carbon-free clusters change nothing — a group needs carbon of its own to alter the compound.
CMB-067 · medium · application · seq 13 · authored (four-panel hydroxyl pick, parallel to seed pool[18]; fresh letters/frames; foil set per the taught permutation discipline) · mcq4
The figure shows the structural formulas of four compounds, Q, R, S, and T. Which compound contains a hydroxyl group?
FIGURE (structural-formula · stimulus) — description: "four small structures in a row: Q is a four-carbon chain with a C=C double bond and only hydrogens attached; R is a plain four-carbon chain with only C–H an… · molecule: "four-compound comparison" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four small structures in a row: Q is a four-carbon chain with a C=C double bond and only hydrogens attached; R is a plain four-carbon chain with only C–H and C–C bonds; S is a four-carbon chain whose end carbon is bonded to an O, which is bonded to an H; T is a four-carbon chain with an O between the second and third carbons, and no H on that O",
"molecule": "four-compound comparison",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
S KEY
Q
R
T
CMB-067 · medium · application · seq 14 · seed:U5-G4/pool[20] (= CMB-067 gateItems[2], James) — INSTANCE FRESHENED at placement per the strict SEED RULING (ethanol is CMB-067's article instance and a base-lexicon material): ethanol -> hexanol, and the hydrogen-count claim de-numbered ('every one of its six hydrogens' -> 'every hydrogen in the molecule'); task, key logic, and misconception classes verbatim · mcq4
A student looks at hexanol's structure — a six-carbon chain that ends in an O–H — and says every hydrogen in the molecule can form hydrogen bonds to water. Which correction is right?
Only the hydrogen bonded to the OXYGEN can hydrogen-bond — the carbon-bonded hydrogens cannot. KEY
No correction is needed — a hydrogen bonds to water the same way whatever atom it is attached to.
The claim is wrong in the other direction — none of hexanol's hydrogens can hydrogen-bond.
The claim becomes right once the water is warmed — heat switches on hydrogen bonding for the carbon-bonded hydrogens.
CMB-068 · medium · application · seq 15 · seed:U5-G4/pool[22] (= CMB-068 gateItems[1], James) — one distractor phrase freshened at placement per the strict SEED RULING: 'anywhere in any structure' also appears verbatim in curated pool[29]'s distractor at A#20 (V-T7 cross-form gram class; both James, the non-curated side freshened); misconception and claim structure verbatim · mcq4
A student examines benzoic acid, a food preservative whose ring frame carries a –COOH, and says: 'I spot an O–H in there, so this compound has a hydroxyl group and should just mix with water like the hydroxyl compounds do.' Which correction is right?
That O–H sits on a carbon with a double-bonded O, so the whole cluster is a carboxyl group — and its signature behavior is making the compound acidic. KEY
No correction is needed — the O–H the student spotted is its own hydroxyl group, so the compound will mix with water like the other hydroxyl compounds.
The student misread the structure — benzoic acid contains no O–H at all.
The O–H is a hydroxyl group, but ring frames block hydroxyl behavior.
Rhubarb leaves owe their sharp sourness to oxalic acid, whose molecules carry –COOH clusters. Which statement correctly connects the structure to the behavior?
The carboxyl group makes a compound acidic — the sourness follows from the –COOH clusters. KEY
The sourness comes from the length of the compound's carbon frame.
The compound turns acidic only once the leaves are cooked.
The –COOH clusters make the compound basic, so the sourness must come from something else.
Propylamine, used in making medicines and farm chemicals, smells sharply 'ammonia-like' — yet it contains no ammonia at all. Its structure is a three-carbon chain ending in an N bonded to two hydrogens. Why do the two smell related?
Propylamine carries an amino group, whose nitrogen-with-two-hydrogens pattern gives it basic, ammonia-like behavior. KEY
The propylamine slowly converts into real ammonia as it sits, and that ammonia is what you smell.
Any sharp-smelling compound smells like ammonia, whether or not it contains nitrogen.
The smell comes from the carbon frame, which ammonia also contains.
CMB-069 · hard · transfer · seq 18 · authored (novel counteracting scenario, parallel to seed pool[26]; fresh surface) · mcq4
A lab manual says compound R 'counteracts leftover acid residue on used glassware.' R's structure is a three-carbon frame that ends in an N bonded to two hydrogens. Why does the structure explain the report?
R's amino group makes it basic — the opposite of acidic — so it counteracts the leftover acid. KEY
R is acidic itself, and one acid cancels another acid out.
R's three-carbon frame soaks up the acid like a sponge.
R works because a carboxyl group must be hidden somewhere in its structure.
CMB-070 · hard · transfer · seq 19 · seed:U5-G4/pool[28] (= CMB-070 gateItems[1] = demo_curated[1], James) — verbatim (field mapping only; medical X-ray-contrast context reviewed against the banned-framings rule at stage 1: no dose/exposure framing — kept, flagged for David) · mcq4
The figure shows the structural formula of serinol, a building block used in making the contrast agents that make body tissues show up on X-ray scans. Which functional groups does the molecule carry?
FIGURE (structural-formula · stimulus) — molecule: "serinol" · description: "a three-carbon chain: the first and third carbons each bonded to an O–H; the second (central) carbon bonded to an N with two hydrogens; all remaining bonds … · style: "clean full structural formula matching the lesson figure's layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"molecule": "serinol",
"description": "a three-carbon chain: the first and third carbons each bonded to an O–H; the second (central) carbon bonded to an N with two hydrogens; all remaining bonds to hydrogens",
"style": "clean full structural formula matching the lesson figure's layout"
}
}
Two hydroxyl groups, one amino group, and no carboxyl group KEY
One hydroxyl group, one amino group, and no carboxyl group
Two hydroxyl groups, one carboxyl group, and no amino group
Two carboxyl groups, one amino group, and no hydroxyl group
CMB-070 · hard · transfer · seq 20 · authored (described-structure report adjudication, parallel to seed pool[29]; the trap runs the OTHER way — a real hydroxyl survives) · mcq4
A student reads a structure whose end carbon carries a double-bonded O and an O–H, and whose middle carbon carries its own lone O–H. The student reports: 'two hydroxyl groups.' What is the correct report?
One carboxyl group and one hydroxyl group — the end O–H is inside the carboxyl; the middle one stands alone. KEY
The student's report is correct — each O–H counts as its own separate hydroxyl group.
Two carboxyl groups — an O–H close to another oxygen upgrades to a carboxyl.
One carboxyl group — a molecule holds one group at a time, so the carboxyl wins.
CMB-070 · medium · application · seq 21 · authored — UNSEEDED FRQ (prod_seeds = []); R14 written production per the blueprint seq-21 case; typed answer is plain words (V-T12: nothing typed requires sub/superscripts) · frq
The figure shows the structural formula of a building block used in making skin-conditioning agents.
FIGURE (structural-formula · stimulus) — description: "a three-carbon chain: the first carbon bonded to two hydrogens and an O–H; the second carbon bonded to one hydrogen and an N with two hydrogens; the third c… · molecule: "2-aminopropan-1-ol" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "a three-carbon chain: the first carbon bonded to two hydrogens and an O–H; the second carbon bonded to one hydrogen and an N with two hydrogens; the third carbon bonded to three hydrogens",
"molecule": "2-aminopropan-1-ol",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
The figure shows the structural formula of a building block used in making skin-conditioning agents.
(a) List every functional group the molecule carries, with a count for each group.
(b) Justify each identification from the structure — say what is bonded to what — and state whether having both an O and an N in the molecule makes a carboxyl group, and why.
(c) Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Part a. List every functional group the molecule carries, with a count for each group.
Model: The molecule carries two functional groups: one hydroxyl group and one amino group.
Part b. Justify each identification from the structure — say what is bonded to what — and state whether having both an O and an N in the molecule makes a carboxyl group, and why.
Model: The first carbon carries an O bonded to one H, and that carbon has no double-bonded O — a hydroxyl group. The middle carbon carries an N bonded to two hydrogens — an amino group. Having an O and an N somewhere in the molecule does NOT make a carboxyl: the carboxyl pattern needs a double-bonded O and an O–H together on one carbon, which no carbon here has.
Part c. Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Model: The hydroxyl group makes the compound mix well with water, because its O–H hydrogen-bonds to water molecules. (Also acceptable: the amino group makes it basic.)
Full model answer. (a) The molecule carries two functional groups: one hydroxyl group and one amino group.
(b) The first carbon carries an O bonded to one H, and that carbon has no double-bonded O — a hydroxyl group. The middle carbon carries an N bonded to two hydrogens — an amino group. Having an O and an N somewhere in the molecule does NOT make a carboxyl: the carboxyl pattern needs a double-bonded O and an O–H together on one carbon, which no carbon here has.
(c) The hydroxyl group makes the compound mix well with water, because its O–H hydrogen-bonds to water molecules. (Also acceptable: the amino group makes it basic.)
One carbon inside a molecule carries a single hydrogen and links to the next carbon through a triple bond. How many covalent bonds does this carbon form in all?
Answer: 4 bonds KEY
also accepted: 4 bonds
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted neighbors instead of bonds — the triple bond is worth three of the carbon's four",
"feedback": null
},
{
"value": 3,
"misconception": "you dropped the C–H bond — the single bond to the hydrogen completes the count: 1 + 3 = 4",
"feedback": null
},
{
"value": 5,
"misconception": "you gave the triple bond four — a triple bond counts as exactly three",
"feedback": null
}
]
feedback
{
"keyExplanation": "Count lines, not neighbors. The single bond to the hydrogen counts 1 and the triple bond counts 3: 1 + 3 = 4 — a carbon atom forms four covalent bonds."
}
CMB-061 · easy · recall · seq 2 · authored (inversion of the whose-drawing pick, parallel to seed pool[2]; the incorrect drawing is the target; misconception families = the seed's designed count errors) · mcq4
Four classmates trade drawings to check each other's work. Whose carbon atom is drawn with an INCORRECT number of bonds?
The classmate whose carbon has one triple bond and two single bonds. KEY
The classmate whose carbon has four single bonds and nothing else.
The classmate whose carbon has two double bonds and nothing else.
The classmate whose carbon has one double bond and two single bonds.
The figure shows one molecule's carbon skeleton. Which skeleton kind does it show?
FIGURE (carbon-skeleton · stimulus) — description: "four carbon atoms joined by single bonds into one closed square loop" · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "four carbon atoms joined by single bonds into one closed square loop",
"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
A ring. KEY
A straight chain.
A branched chain.
A ring with one extra carbon attached.
CMB-062 · medium · application · seq 4 · authored (octet-arithmetic comparison, parallel to seed pool[4]; sulfur chosen because oxygen/fluorine are CMB-062 WE vocabulary and nitrogen is the seed's own comparison) · mcq4
Sulfur has six valence electrons and typically forms two bonds in simple molecules. Carbon forms four. Which comparison explains the difference?
Carbon needs 8 − 4 = 4 more electrons, so it shares four pairs; sulfur needs 8 − 6 = 2 more, so it shares two pairs. KEY
Carbon is the larger atom of the two, so more neighboring atoms can physically fit into the space around it.
Sulfur starts with fewer valence electrons, so it has fewer available to share.
Carbon reaches four bonds by also using two of its inner-shell electrons.
CMB-062 · medium · application · seq 5 · authored (under-count diagnosis, parallel to seed pool[5]; three-bond variant) · mcq4
A drawing shows a carbon atom with only three bonds, and the student calls the structure finished. What does the octet count say?
Three shared pairs leave the carbon at 4 + 3 = 7, one short of the octet — that carbon needs a fourth bond. KEY
The structure is fine as drawn — three bonds is all a carbon atom needs when the molecule is a small one.
The carbon is one OVER the octet, so a bond must be removed.
The octet count cannot be applied until every hydrogen is drawn in.
The figure shows the carbon skeletons of two molecules, T and U. Which description is correct?
FIGURE (carbon-skeleton · stimulus) — description: "two skeletons side by side: T is seven carbon atoms, six joined in a row with the seventh bonded to the third carbon of the row; U is seven carbon atoms joi… · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "two skeletons side by side: T is seven carbon atoms, six joined in a row with the seventh bonded to the third carbon of the row; U is seven carbon atoms joined in one unbranched row",
"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
T is a branched chain and U is a straight chain. KEY
T is a straight chain and U is a branched chain.
T is a ring with an attached carbon and U is a straight chain.
A modeling app lists five different skeletons that can be built from one molecular formula. A student objects that the app has drawn one compound five times. Which correction is right?
The app has listed five different compounds — every different arrangement of the same atoms is a different compound. KEY
The student is right — one formula always names exactly one compound, however many skeletons fit it.
They are different compounds only if their boiling points happen to differ.
They are different compounds only if the app also changes the formula.
CMB-064 · medium · application · seq 8 · authored (bond-count thought experiment isolating the four-bond ingredient, per the CMB-064 contrast discipline) · mcq4
Suppose carbon atoms formed only TWO bonds each. What would happen to the variety of carbon compounds?
Skeletons could only be unbranched strings or loops — no forks — so far fewer arrangements would exist. KEY
Nothing would change — the variety comes from the many elements carbon pairs with.
The variety would grow — fewer bonds leave each atom more freedom.
Two-bond carbons could still branch, so the variety would stay the same.
CMB-065 · medium · application · seq 9 · authored (formula production with a halogen count, parallel to seed pool[12]) · text
The figure shows the structural formula of a laboratory solvent. From the structure, write its molecular formula.
FIGURE (structural-formula · stimulus) — description: "one C symbol bonded by single lines to two H symbols and two Cl symbols" · molecule: "dichloromethane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "one C symbol bonded by single lines to two H symbols and two Cl symbols",
"molecule": "dichloromethane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: CH₂Cl₂ KEY
also accepted: CH2Cl2
wrongValueDiagnostics
[
{
"value": "CH₄",
"misconception": "you read the two Cl symbols as hydrogens — two of the four attachments are chlorines",
"feedback": "This answer is wrong — you read the two Cl symbols as hydrogens — two of the four attachments are chlorines."
},
{
"value": "CH₂Cl",
"misconception": "you counted only one of the chlorines — the carbon carries two Cl symbols",
"feedback": "This answer is wrong — you counted only one of the chlorines — the carbon carries two Cl symbols."
},
{
"value": "CH₃Cl",
"misconception": "you traded a chlorine for a hydrogen — the structure shows two of each",
"feedback": "This answer is wrong — you traded a chlorine for a hydrogen — the structure shows two of each."
}
]
feedback
{
"keyExplanation": "Count the atoms: one carbon, two hydrogens, and two chlorines, so the formula is CH₂Cl₂. All four of the carbon's lines are single bonds — two to H and two to Cl.",
"anticipatedWrong": [
{
"value": "CH₄",
"misconception": "you read the two Cl symbols as hydrogens — two of the four attachments are chlorines",
"feedback": "This answer is wrong — you read the two Cl symbols as hydrogens — two of the four attachments are chlorines."
},
{
"value": "CH₂Cl",
"misconception": "you counted only one of the chlorines — the carbon carries two Cl symbols",
"feedback": "This answer is wrong — you counted only one of the chlorines — the carbon carries two Cl symbols."
},
{
"value": "CH₃Cl",
"misconception": "you traded a chlorine for a hydrogen — the structure shows two of each",
"feedback": "This answer is wrong — you traded a chlorine for a hydrogen — the structure shows two of each."
}
]
}
CMB-065 · medium · application · seq 10 · authored (bond-kind count on a ring, parallel to seed pool[13]; the closing bond is the designed trap) · numeric
The figure shows the structural formula of a ring-shaped compound. How many C–C bonds does the structure contain?
FIGURE (structural-formula · stimulus) — description: "four C symbols joined by single lines into a closed loop; each carbon also bonded to two H symbols" · molecule: "cyclobutane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four C symbols joined by single lines into a closed loop; each carbon also bonded to two H symbols",
"molecule": "cyclobutane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: 4 bonds KEY
also accepted: 4 bonds
wrongValueDiagnostics
[
{
"value": 3,
"misconception": "you counted the loop as an open row — the bond that closes the ring counts too",
"feedback": null
},
{
"value": 8,
"misconception": "you counted the C–H bonds instead — the question asks for C–C bonds only",
"feedback": null
},
{
"value": 12,
"misconception": "you counted every bond in the structure — only the four ring lines are C–C bonds",
"feedback": null
}
]
feedback
{
"keyExplanation": "Trace the ring: each of the four carbons bonds to the next, and the fourth bonds back to the first — four C–C bonds in all. The eight C–H bonds are bonds too, but not C–C bonds."
}
The figure shows the structural formula of a molecule used as a refrigerant. Which full reading of the structure is correct?
FIGURE (structural-formula · stimulus) — description: "two C symbols joined by a single line; the first carbon bonded to three H symbols, the second bonded to one H symbol and two F symbols" · molecule: "difluoroethane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "two C symbols joined by a single line; the first carbon bonded to three H symbols, the second bonded to one H symbol and two F symbols",
"molecule": "difluoroethane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
C₂H₄F₂, containing one C–C single bond, four C–H bonds, and two C–F bonds. KEY
C₂H₄F₂, with the two F symbols bonded to each other.
C₂H₆, reading the F symbols as hydrogens.
C₄H₄F₂, counting each F symbol as another carbon.
CMB-066 · medium · application · seq 12 · seed:U5-G4/pool[17] (= CMB-066 gateItems[2], James) — leading-None distractor REPLACED with a substantive misconception-keyed one (V-T5 close-variant class; opportunistic rule, ANSWERS #2; recorded in seed_placement.json) · mcq4
Three compounds carry the same functional group on one-carbon, four-carbon, and six-carbon frames. A fourth compound is a plain six-carbon chain with no attached group. Which compound should behave the LEAST like the other three?
The plain six-carbon chain, because it lacks the shared functional group. KEY
The one-carbon compound, because its frame is the smallest.
The six-carbon compound with the group, because it matches the plain chain's length.
It cannot be decided from the structures alone — behavior likeness only shows up in lab tests.
CMB-067 · medium · application · seq 13 · authored (four-panel hydroxyl pick with the carboxyl trap and a mid-frame key, parallel to seed pool[18]) · mcq4
The figure shows the structural formulas of four compounds, F, G, H, and J. Which compound contains a hydroxyl group?
FIGURE (structural-formula · stimulus) — description: "four small structures in a row: F is a three-carbon chain whose end carbon carries a double-bonded O and one H, with no O–H anywhere; G is a plain three-car… · molecule: "four-compound comparison" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four small structures in a row: F is a three-carbon chain whose end carbon carries a double-bonded O and one H, with no O–H anywhere; G is a plain three-carbon chain with only C–H and C–C bonds; H is a three-carbon chain whose MIDDLE carbon is bonded to an O, which is bonded to an H; J is a three-carbon chain whose end carbon is bonded to a Cl",
"molecule": "four-compound comparison",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
H KEY
F
G
J
CMB-067 · medium · application · seq 14 · authored (lookalike-pair mixing read, parallel to seed pool[19]; compounds left unnamed) · mcq4
Two clear liquids are built on the same six-carbon frame: one carries an –OH on its end carbon, the other carries only hydrogens. Only one mixes well with water. Which reading explains the difference?
The –OH compound mixes well — its hydroxyl group hydrogen-bonds to water molecules. KEY
The bare-frame liquid mixes better — with nothing attached, it slides into the gaps in the water more smoothly.
The two mix equally well — their frames are the same length.
The –OH compound mixes better because its extra oxygen makes it heavier.
The figure shows the structural formulas of four compounds, R, S, T, and U. Which compound contains a carboxyl group?
FIGURE (structural-formula · stimulus) — description: "four small structures in a row: R is a two-carbon chain whose end carbon is bonded to an O, which is bonded to an H; S is a two-carbon chain whose end carbo… · molecule: "four-compound comparison" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four small structures in a row: R is a two-carbon chain whose end carbon is bonded to an O, which is bonded to an H; S is a two-carbon chain whose end carbon carries a double-bonded O only, with no O–H anywhere; T is a two-carbon chain whose end carbon carries a double-bonded O and an O–H together; U is a plain two-carbon chain with only C–H and C–C bonds",
"molecule": "four-compound comparison",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
T KEY
R
S
U
CMB-068 · medium · application · seq 16 · authored (behavior-card entry from the group, parallel to seed pool[23]) · mcq4
A compound's structure shows a five-carbon frame ending in a –COOH cluster. Which entry belongs on its behavior card?
Acidic — the carboxyl group makes a compound acidic. KEY
Basic — oxygen-rich clusters push a compound the basic way.
No characteristic behavior — five carbons dilute any group's effect.
It behaves exactly like the bare five-carbon chain.
The figure shows the structural formulas of four compounds, G, H, J, and K. Which compound contains an amino group?
FIGURE (structural-formula · stimulus) — description: "four small structures in a row: G is a four-carbon chain whose end carbon is bonded to an O, which is bonded to an H; H is a plain four-carbon chain with on… · molecule: "four-compound comparison" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four small structures in a row: G is a four-carbon chain whose end carbon is bonded to an O, which is bonded to an H; H is a plain four-carbon chain with only C–H and C–C bonds; J is a four-carbon chain whose end carbon is bonded to an N with two hydrogens; K is a four-carbon chain whose end carbon carries a double-bonded O and an O–H together",
"molecule": "four-compound comparison",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
J KEY
G
H
K
CMB-069 · hard · transfer · seq 18 · authored (structure-only routing transfer, parallel to seed pool[26]) · mcq4
A technician sorts reagents into acid-like and base-like bins using structures alone. Compound T's structure ends in an N bonded to two hydrogens. Which bin, and why?
Base-like — the N with two hydrogens is an amino group, and the amino group makes a compound basic. KEY
Acid-like — sharp-smelling nitrogen compounds sort with the acids.
Neither bin — a structure drawing alone can never place a compound; only lab behavior can.
Acid-like — any group containing hydrogen atoms donates sourness.
CMB-070 · hard · transfer · seq 19 · authored (two-group scan, parallel to curated seeds pool[27]/[28]; fresh real molecule, option set keeps the promote/misread/phantom-carboxyl trap lanes) · mcq4
The figure shows the structural formula of a compound used in making moisturizer thickeners. Which functional groups does the molecule carry?
FIGURE (structural-formula · stimulus) — description: "a three-carbon chain: the first carbon bonded to two hydrogens and an O–H; the second carbon bonded to two hydrogens; the third carbon bonded to two hydroge… · molecule: "3-aminopropan-1-ol" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "a three-carbon chain: the first carbon bonded to two hydrogens and an O–H; the second carbon bonded to two hydrogens; the third carbon bonded to two hydrogens and an N with two hydrogens",
"molecule": "3-aminopropan-1-ol",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
One hydroxyl group and one amino group, with no carboxyl group KEY
One amino group and one carboxyl group, with no hydroxyl group
Two hydroxyl groups and no amino group
One hydroxyl group, one amino group, and one carboxyl group
CMB-070 · hard · transfer · seq 20 · authored (scattered-atoms-make-a-group error, parallel to seed pool[29]'s report-adjudication class) · mcq4
A structure ends in an N bonded to two hydrogens on one end and a lone O–H on the other. A student reports: 'one carboxyl group, because I can see both an O and an N in the molecule.' What is the correct report?
One amino group and one hydroxyl group — no single carbon carries a double-bonded O with an O–H, so there is no carboxyl. KEY
The student is right — an O atom and an N atom anywhere in the same molecule add up to one carboxyl group.
One amino group only — a lone O–H does not count as a group.
One hydroxyl group only — the N with two hydrogens is part of the frame.
CMB-070 · medium · application · seq 21 · authored — UNSEEDED FRQ (prod_seeds = []); R14 written production per the blueprint seq-21 case; typed answer is plain words (V-T12: nothing typed requires sub/superscripts) · frq
The figure shows the structural formula of a compound studied in sports-recovery research.
FIGURE (structural-formula · stimulus) — description: "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second carbon bonded to one hydrogen and its own O–H; the third carbon bond… · molecule: "2-hydroxybutanoic acid" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second carbon bonded to one hydrogen and its own O–H; the third carbon bonded to two hydrogens; the fourth carbon bonded to three hydrogens",
"molecule": "2-hydroxybutanoic acid",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
The figure shows the structural formula of a compound studied in sports-recovery research.
(a) List every functional group the molecule carries, with a count for each group.
(b) Justify each identification from the structure — say what is bonded to what — and state whether the two O–H clusters make two hydroxyl groups, and why.
(c) Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Part a. List every functional group the molecule carries, with a count for each group.
Model: The molecule carries two functional groups: one carboxyl group and one hydroxyl group.
Part b. Justify each identification from the structure — say what is bonded to what — and state whether the two O–H clusters make two hydroxyl groups, and why.
Model: The first carbon carries a double-bonded O together with an O–H — the carboxyl pattern. The second carbon carries its own O–H with no double-bonded O on that carbon — a genuine hydroxyl. The two O–H clusters do NOT make two hydroxyls: the one on the double-bonded-O carbon is counted inside the carboxyl, so exactly one hydroxyl remains.
Part c. Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Model: The carboxyl group makes the compound acidic. (Also acceptable: the hydroxyl group helps it mix well with water.)
Full model answer. (a) The molecule carries two functional groups: one carboxyl group and one hydroxyl group.
(b) The first carbon carries a double-bonded O together with an O–H — the carboxyl pattern. The second carbon carries its own O–H with no double-bonded O on that carbon — a genuine hydroxyl. The two O–H clusters do NOT make two hydroxyls: the one on the double-bonded-O carbon is counted inside the carboxyl, so exactly one hydroxyl remains.
(c) The carboxyl group makes the compound acidic. (Also acceptable: the hydroxyl group helps it mix well with water.)
A carbon atom sits inside a ring, bonded to two neighboring ring carbons and to two hydrogens. How many covalent bonds does that carbon form?
Answer: 4 bonds KEY
also accepted: 4 bonds
wrongValueDiagnostics
[
{
"value": 2,
"misconception": "you counted only the ring neighbors — the two C–H bonds belong to the count as well",
"feedback": null
},
{
"value": 3,
"misconception": "you dropped one of the four connections — two ring bonds plus two C–H bonds make 2 + 2 = 4",
"feedback": null
},
{
"value": 8,
"misconception": "you counted every bond twice — doubling this carbon's four real connections gives 8, but each bond counts once: 2 + 2 = 4",
"feedback": null
}
]
feedback
{
"keyExplanation": "Ring or chain, the count is the same. Two bonds to ring carbons plus two bonds to hydrogens give 2 + 2 = 4 — a carbon atom forms four covalent bonds."
}
A drawing checklist says: 'count a double bond as two lines and a triple bond as three; a correct carbon shows four lines in total.' Which drawn carbon passes the check?
A carbon with one triple bond and one single bond. KEY
A carbon with three single bonds and nothing else.
A carbon with one double bond and three single bonds.
A carbon with two double bonds and one single bond.
The figure shows a molecule's carbon skeleton. Classify the skeleton it shows.
FIGURE (carbon-skeleton · stimulus) — description: "six carbon atoms: five joined in a row, with the sixth bonded to the middle carbon of the row" · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "six carbon atoms: five joined in a row, with the sixth bonded to the middle carbon of the row",
"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
A branched chain. KEY
A straight chain.
A ring.
A ring with one attached carbon.
CMB-062 · medium · application · seq 4 · authored (space-error correction, parallel to seed pool[3]'s wrong-why class) · mcq4
A student says: 'Carbon forms four bonds because four neighboring atoms are the most that can physically fit around one carbon.' Which correction is right?
The count comes from electron arithmetic, not space — carbon needs 8 − 4 = 4 more electrons, so it shares four pairs. KEY
The student is right — crowding around the small carbon atom is what stops a fifth bond from ever forming.
The student has the wrong number — up to six atoms can fit, so carbon forms six bonds.
The correction is that carbon TRANSFERS electrons to exactly four neighbors.
CMB-062 · medium · application · seq 5 · authored (rule-identification variant of the five-bond error, parallel to seed pool[5]) · mcq4
A molecule-building app refuses to attach a fifth bond to any carbon atom. Which rule is the app enforcing?
Carbon's octet: with four valence electrons of its own, a fifth shared pair would push the count past eight. KEY
A style rule — five bond lines drawn around one atom symbol are too crowded for the app to display neatly.
A column rule — atoms in carbon's column may form five bonds, and the app rounds down.
A size rule — a fifth atom cannot physically reach the carbon.
The figure shows the carbon skeletons of two molecules, V and W. Which description is correct?
FIGURE (carbon-skeleton · stimulus) — description: "two skeletons side by side: V is six carbon atoms, five joined into a closed ring with the sixth bonded to one ring carbon; W is six carbon atoms joined in … · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "carbon-skeleton",
"description": "two skeletons side by side: V is six carbon atoms, five joined into a closed ring with the sixth bonded to one ring carbon; W is six carbon atoms joined in one unbranched row",
"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
V is a ring with an attached carbon and W is a straight chain. KEY
V is a branched chain and W is a ring.
V is a plain ring and W is a branched chain.
Both are rings of different sizes.
CMB-064 · medium · application · seq 7 · authored (evidence-read inversion of the identity rule, parallel to seed pool[9]) · mcq4
Two bottled liquids have exactly the same molecular formula, yet one boils noticeably lower than the other. What does this show?
The same atoms are arranged on different skeletons — different arrangements are different compounds, with different properties. KEY
One of the two boiling-point measurements must be wrong — the same molecular formula forces the same boiling point.
One bottle must be contaminated — pure samples of one formula never differ.
The liquids differ only in their temperature history, not in identity.
CMB-064 · medium · application · seq 8 · authored (Group-14 contrast with a fresh element, same argument class as seed pool[11] by design — same-seq parallel) · mcq4
Tin occupies carbon's own column of the periodic table, three rows farther down, and it too forms four bonds — yet tin builds only a small sliver of carbon's compound count. Which carbon fact best explains the gap?
Carbon's bonds to other carbons are strong, so its long chains, branches, and rings hold together. KEY
Carbon atoms are far lighter, and lighter atoms always form more compounds.
Carbon can borrow a fifth bond when a skeleton needs one.
Carbon compounds come from living things, which manufacture the variety.
CMB-065 · medium · application · seq 9 · authored (formula production with a single halogen, parallel to seed pool[12]) · text
The figure shows the structural formula of a compound tested as a low-boiling refrigerant. From the structure shown, write its molecular formula.
FIGURE (structural-formula · stimulus) — description: "two C symbols joined by a single line; the first carbon bonded to three H symbols, the second bonded to two H symbols and one F symbol" · molecule: "fluoroethane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "two C symbols joined by a single line; the first carbon bonded to three H symbols, the second bonded to two H symbols and one F symbol",
"molecule": "fluoroethane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: C₂H₅F KEY
also accepted: C2H5F
wrongValueDiagnostics
[
{
"value": "C₂H₆",
"misconception": "you read the F symbol as another hydrogen — one attachment is a fluorine",
"feedback": "This answer is wrong — you read the F symbol as another hydrogen — one attachment is a fluorine."
},
{
"value": "C₂H₅",
"misconception": "you dropped the fluorine — every symbol in the structure goes into the formula",
"feedback": "This answer is wrong — you dropped the fluorine — every symbol in the structure goes into the formula."
},
{
"value": "C₂H₆F",
"misconception": "you gave the fluorine's carbon a full set of hydrogens — the F occupies one of its four lines, so the hydrogens count 3 + 2 = 5",
"feedback": "This answer is wrong — you gave the fluorine's carbon a full set of hydrogens — the F occupies one of its four lines, so the hydrogens count 3 + 2 = 5."
}
]
feedback
{
"keyExplanation": "Count the atoms: two carbons, hydrogens 3 + 2 = 5, and one fluorine, so the formula is C₂H₅F. The C–F line is a bond like any other and its atom must appear in the formula.",
"anticipatedWrong": [
{
"value": "C₂H₆",
"misconception": "you read the F symbol as another hydrogen — one attachment is a fluorine",
"feedback": "This answer is wrong — you read the F symbol as another hydrogen — one attachment is a fluorine."
},
{
"value": "C₂H₅",
"misconception": "you dropped the fluorine — every symbol in the structure goes into the formula",
"feedback": "This answer is wrong — you dropped the fluorine — every symbol in the structure goes into the formula."
},
{
"value": "C₂H₆F",
"misconception": "you gave the fluorine's carbon a full set of hydrogens — the F occupies one of its four lines, so the hydrogens count 3 + 2 = 5",
"feedback": "This answer is wrong — you gave the fluorine's carbon a full set of hydrogens — the F occupies one of its four lines, so the hydrogens count 3 + 2 = 5."
}
]
}
CMB-065 · medium · application · seq 10 · authored (bond-kind count across a triple bond, parallel to seed pool[13]) · numeric
The figure shows the structural formula of a test compound. How many C–H bonds does it contain?
FIGURE (structural-formula · stimulus) — description: "four C symbols in a row: the first and second joined by three parallel lines (a triple bond), the others by single lines; the first carbon bonded to one H s… · molecule: "butyne (end triple bond)" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four C symbols in a row: the first and second joined by three parallel lines (a triple bond), the others by single lines; the first carbon bonded to one H symbol, the third to two H symbols, the fourth to three H symbols",
"molecule": "butyne (end triple bond)",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: 6 bonds KEY
also accepted: 6 bonds
wrongValueDiagnostics
[
{
"value": 11,
"misconception": "you counted every line in the drawing — the triple bond's three lines and the C–C singles are not C–H bonds",
"feedback": null
},
{
"value": 5,
"misconception": "you dropped the triple-bond carbon's single hydrogen — it counts: 1 + 2 + 3 = 6",
"feedback": null
},
{
"value": 10,
"misconception": "you ignored the triple bond and gave every carbon a full set — the true count is 1 + 0 + 2 + 3 = 6",
"feedback": null
}
]
feedback
{
"keyExplanation": "Trace each line from a carbon to an H symbol: 1 on the first carbon, none on the second, 2 on the third, and 3 on the fourth give 1 + 2 + 3 = 6 C–H bonds. The triple bond and the C–C singles are bonds, but not C–H bonds."
}
CMB-065 · medium · application · seq 11 · authored (full-reading pick on a ring, parallel to seed pool[14]) · mcq4
The figure shows the structural formula of a ring-shaped molecule once used in medicine. Which full reading of the structure is correct?
FIGURE (structural-formula · stimulus) — description: "three C symbols joined by single lines into a closed triangle; each carbon also bonded to two H symbols" · molecule: "cyclopropane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "three C symbols joined by single lines into a closed triangle; each carbon also bonded to two H symbols",
"molecule": "cyclopropane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
C₃H₆, containing three C–C single bonds and six C–H bonds, with no double bond anywhere. KEY
C₃H₆, containing one C=C double bond hidden in the ring.
C₃H₈, with the ring opened and every carbon carrying a full set of hydrogens.
Three separate CH₂ molecules drawn close together.
CMB-066 · medium · application · seq 12 · authored (same-group-different-frames prediction, parallel to seed pool[17]'s comparison class) · mcq4
Two liquids carry the same functional group — one on a two-carbon frame, the other on a nine-carbon frame. A student expects completely unrelated behavior. Which reply is right?
The same functional group brings its characteristic behavior to whatever frame carries it — the two share their signature behavior. KEY
The student is right — behavior scales with frame size, so frames this different guarantee thoroughly different behavior.
The shared group guarantees identical compounds — same group means the same substance.
The shared behavior appears once the two liquids are mixed together.
CMB-067 · medium · application · seq 13 · authored (four-panel hydroxyl pick with the lone-carbonyl foil, parallel to seed pool[18]) · mcq4
The figure shows the structural formulas of four compounds, L, M, N, and P. Which compound contains a hydroxyl group?
FIGURE (structural-formula · stimulus) — description: "four small structures in a row: L is a five-carbon chain with a C=C double bond and only hydrogens attached; M is a five-carbon chain whose end carbon carri… · molecule: "four-compound comparison" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
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"figureType": "structural-formula",
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"molecule": "four-compound comparison",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
P KEY
L
M
N
CMB-067 · medium · application · seq 14 · authored (design-a-change application of the hydroxyl -> water link) · mcq4
A lab wants a plain-chain carbon compound to mix more readily with water. Which change to its structure would do the most?
Attach a hydroxyl group — an O–H on the frame hydrogen-bonds to water molecules. KEY
Lengthen the carbon frame by attaching several more plain carbons.
A label lists hexanoic acid, responsible for the sharp smell of some cheeses. Its structure is a six-carbon frame whose end carbon carries a double-bonded O and an O–H. A student calls it 'a hydroxyl compound, because there is an O–H.' Which correction is right?
That O–H sits on a carbon that also carries a double-bonded O — the cluster is a carboxyl group, and it makes the compound acidic. KEY
No correction is needed — every O–H, wherever it sits in a structure, is always its own separate hydroxyl group.
The student misread the drawing — there is no real O–H in the structure.
It is a hydroxyl group, but six-carbon frames switch hydroxyl behavior off.
CMB-068 · medium · application · seq 16 · authored (frame-drowns-the-group critique, parallel to seed pool[16]'s size error applied in the carboxyl lane) · mcq4
A student says: 'This compound can't really be acidic — its frame is nine carbons long, and that much frame drowns out one little cluster.' The structure ends in a –COOH. Which reply is right?
The carboxyl group brings acidity to any frame — the same group means the same characteristic behavior, long frame or short. KEY
The student is right — once a frame passes six or so carbons, it drowns out whatever groups it carries.
The student is right unless the compound carries a second –COOH as backup.
The reply should be that the –COOH makes it basic instead.
CMB-069 · medium · application · seq 17 · authored (behavior-card entry from the amino group, parallel to seed pool[25]'s group-to-behavior read; fresh amine instance) · mcq4
Pentylamine's structure is a five-carbon frame ending in an N bonded to two hydrogens. Which behavior should a student predict for it?
Basic — the amino group makes a compound basic, the chemical opposite of acidic. KEY
Acidic — nitrogen clusters behave like the carboxyl cluster.
Sour-tasting, because its five-carbon frame stores sourness.
No prediction is possible from a single small group.
CMB-069 · hard · transfer · seq 18 · authored (two-structure routing transfer; the carboxyl foil is the taught opposite from CMB-068, used here as a foil only — the keyed skill is the amino -> basic link) · mcq4
Two spill-response powders sit on a shelf: powder 1's molecules end in an N bonded to two hydrogens; powder 2's molecules end in a carbon carrying a double-bonded O and an O–H. Which powder counteracts an ACID spill, and why?
Powder 1 — its amino group makes it basic, the chemical opposite of acidic. KEY
Powder 2 — its carboxyl group neutralizes acids of its own kind.
Both work equally — any functional group counteracts a spill.
Neither — powders need long carbon frames to act on spills.
CMB-070 · hard · transfer · seq 19 · authored (three-group scan with the double-count trap in BOTH directions; fresh real molecule) · mcq4
The figure shows the structural formula of malic acid, which gives green apples their tart bite. Which functional groups does the molecule carry?
FIGURE (structural-formula · stimulus) — description: "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second carbon bonded to one hydrogen and its own O–H; the third carbon bond… · molecule: "malic acid" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
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"figureType": "structural-formula",
"description": "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second carbon bonded to one hydrogen and its own O–H; the third carbon bonded to two hydrogens; the fourth carbon carrying a double-bonded O and an O–H",
"molecule": "malic acid",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Two carboxyl groups and one hydroxyl group KEY
Three hydroxyl groups and no carboxyl group
Two carboxyl groups only — the middle O–H belongs to one of them
One carboxyl group and two hydroxyl groups
CMB-070 · hard · transfer · seq 20 · authored (three-group over-report adjudication, the seed pool[29] trap on a two-group molecule) · mcq4
A structure's end carbon carries a double-bonded O and an O–H, and a middle carbon carries an N bonded to two hydrogens. A student reports: 'a carboxyl, an amino, AND a hydroxyl — three groups.' What is the correct report?
One carboxyl group and one amino group — the O–H the student counted separately sits inside the carboxyl. KEY
The student's report is correct — the O–H counts both inside and outside the carboxyl.
One amino group and one hydroxyl group — the double-bonded O breaks the carboxyl apart.
One carboxyl group only — an amino group cannot share a molecule with a carboxyl.
CMB-070 · medium · application · seq 21 · authored — UNSEEDED FRQ (prod_seeds = []); R14 written production per the blueprint seq-21 case; typed answer is plain words (V-T12: nothing typed requires sub/superscripts) · frq
The figure shows the structural formula of a compound found in plant tissues.
FIGURE (structural-formula · stimulus) — description: "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second carbon bonded to one hydrogen and an N with two hydrogens; the third… · molecule: "homoserine" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
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"molecule": "homoserine",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
The figure shows the structural formula of a compound found in plant tissues.
(a) List every functional group the molecule carries, with a count for each group.
(b) Justify each identification from the structure — say what is bonded to what — and state whether the two O–H clusters make two hydroxyl groups, and why.
(c) Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Part a. List every functional group the molecule carries, with a count for each group.
Model: The molecule carries three functional groups: one carboxyl group, one amino group, and one hydroxyl group.
Part b. Justify each identification from the structure — say what is bonded to what — and state whether the two O–H clusters make two hydroxyl groups, and why.
Model: The first carbon carries a double-bonded O together with an O–H — a carboxyl group. The second carbon carries an N bonded to two hydrogens — an amino group. The end carbon carries a lone O–H with no double-bonded O — a hydroxyl group. The two O–H clusters do NOT make two hydroxyls: the first one is counted inside the carboxyl.
Part c. Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Model: The carboxyl group makes the compound acidic. (Also acceptable: the amino group makes it basic, or the hydroxyl group helps it mix well with water.)
Full model answer. (a) The molecule carries three functional groups: one carboxyl group, one amino group, and one hydroxyl group.
(b) The first carbon carries a double-bonded O together with an O–H — a carboxyl group. The second carbon carries an N bonded to two hydrogens — an amino group. The end carbon carries a lone O–H with no double-bonded O — a hydroxyl group. The two O–H clusters do NOT make two hydroxyls: the first one is counted inside the carboxyl.
(c) The carboxyl group makes the compound acidic. (Also acceptable: the amino group makes it basic, or the hydroxyl group helps it mix well with water.)
A carbon atom at a branch point is bonded to three other carbons and to one hydrogen. How many covalent bonds does that carbon form?
Answer: 4 bonds KEY
also accepted: 4 bonds
wrongValueDiagnostics
[
{
"value": 3,
"misconception": "you counted only the carbon neighbors — the C–H bond belongs to the count as well",
"feedback": null
},
{
"value": 2,
"misconception": "you counted connection kinds, not bonds — carbons and hydrogen make two kinds, but the three C–C bonds count separately: 3 + 1 = 4",
"feedback": null
},
{
"value": 5,
"misconception": "you added an extra bond for the branch point — branching carbons still form exactly four",
"feedback": null
}
]
feedback
{
"keyExplanation": "A branch point changes nothing about the count. Three bonds to carbons plus one bond to a hydrogen give 3 + 1 = 4 — a carbon atom forms four covalent bonds."
}
The figure shows a single molecule's carbon skeleton. Tracing its bonds, which skeleton kind is drawn?
FIGURE (carbon-skeleton · stimulus) — description: "seven carbon atoms joined one after another in a single unbranched row" · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
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"figureShape": "stimulus",
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"description": "seven carbon atoms joined one after another in a single unbranched row",
"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
The figure shows the carbon skeletons of two molecules, X and Y. Which description is correct?
FIGURE (carbon-skeleton · stimulus) — description: "two skeletons side by side: X is four carbon atoms joined into one closed loop; Y is four carbon atoms, three joined in a row with the fourth bonded to the … · caption: "Hydrogens omitted for clarity." · style: "same skeleton-drawing convention as the lesson figures"raw spec
{
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"caption": "Hydrogens omitted for clarity.",
"style": "same skeleton-drawing convention as the lesson figures"
}
}
X is a ring and Y is a branched chain. KEY
X is a branched chain and Y is a ring.
X is a ring and Y is a straight chain.
Both are branched chains.
CMB-064 · medium · application · seq 7 · authored (bent-on-paper correction, parallel to seed pool[9]'s identity class) · mcq4
A student says a branched skeleton 'is just the straight chain bent over on paper.' Which reply is right?
Bending a drawing changes nothing — but a branch is different BONDING, one carbon joined to three others: a different compound. KEY
The student is right — every skeleton drawn from one molecular formula is the same compound seen from a different angle on the page.
The branch only matters for very long chains.
The two become the same compound once the sample is melted.
CMB-064 · medium · application · seq 8 · authored (growth-mechanism why, riding the taught skeleton-choices-multiply rule line) · mcq4
Adding one more carbon atom to a skeleton MULTIPLIES the number of possible compounds instead of adding just one. Why?
Each new carbon offers new places to extend, fork, or loop — and every different arrangement of the same atoms is a different compound. KEY
Each new carbon makes the molecule heavier, and heavier formulas are counted more generously.
Each new carbon adds exactly one new compound to the list — the growth is steady and additive, never multiplying.
Extra carbons add compounds only when they close a new ring.
CMB-065 · medium · application · seq 9 · authored (formula production, parallel to seed pool[12]; fresh end-double-bond five-carbon structure) · text
The figure shows the structural formula of a polymer-plant feedstock. Write the compound's molecular formula from the structure.
FIGURE (structural-formula · stimulus) — description: "five C symbols in a row: the first and second joined by two parallel lines (a double bond), the rest by single lines; the first carbon bonded to two H symbo… · molecule: "pentene" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
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"molecule": "pentene",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: C₅H₁₀ KEY
also accepted: C5H10
wrongValueDiagnostics
[
{
"value": "C₅H₁₂",
"misconception": "you gave the double-bonded carbons full sets of hydrogens — the double bond uses two lines at each of its carbons: the count is 2 + 1 + 2 + 2 + 3 = 10",
"feedback": "This answer is wrong — you gave the double-bonded carbons full sets of hydrogens — the double bond uses two lines at each of its carbons: the count is 2 + 1 + 2 + 2 + 3 = 10."
},
{
"value": "C₆H₁₀",
"misconception": "you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons",
"feedback": "This answer is wrong — you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons."
},
{
"value": "C₅H₈",
"misconception": "you charged the double bond twice at each carbon — it costs the pair just one hydrogen each, so the count is 2 + 1 + 2 + 2 + 3 = 10",
"feedback": "This answer is wrong — you charged the double bond twice at each carbon — it costs the pair just one hydrogen each, so the count is 2 + 1 + 2 + 2 + 3 = 10."
}
]
feedback
{
"keyExplanation": "Count the atoms: five carbons, and hydrogens 2 + 1 + 2 + 2 + 3 = 10, so the formula is C₅H₁₀. The two parallel lines at the chain's end are one C=C double bond.",
"anticipatedWrong": [
{
"value": "C₅H₁₂",
"misconception": "you gave the double-bonded carbons full sets of hydrogens — the double bond uses two lines at each of its carbons: the count is 2 + 1 + 2 + 2 + 3 = 10",
"feedback": "This answer is wrong — you gave the double-bonded carbons full sets of hydrogens — the double bond uses two lines at each of its carbons: the count is 2 + 1 + 2 + 2 + 3 = 10."
},
{
"value": "C₆H₁₀",
"misconception": "you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons",
"feedback": "This answer is wrong — you counted the double bond as an extra carbon — two parallel lines are one bond between the SAME two carbons."
},
{
"value": "C₅H₈",
"misconception": "you charged the double bond twice at each carbon — it costs the pair just one hydrogen each, so the count is 2 + 1 + 2 + 2 + 3 = 10",
"feedback": "This answer is wrong — you charged the double bond twice at each carbon — it costs the pair just one hydrogen each, so the count is 2 + 1 + 2 + 2 + 3 = 10."
}
]
}
CMB-065 · medium · application · seq 10 · authored (bond-kind count, parallel to seed pool[13]; fresh four-carbon bromo chain — 'bromine' appears in no visible text) · numeric
The figure shows the structural formula of a bottled sample. Counting from the structure, how many C–H bonds does it contain?
FIGURE (structural-formula · stimulus) — description: "four C symbols joined in a row by single lines; the first carbon bonded to three H symbols, the second and third each bonded to two H symbols, the fourth bo… · molecule: "bromobutane" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
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"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four C symbols joined in a row by single lines; the first carbon bonded to three H symbols, the second and third each bonded to two H symbols, the fourth bonded to two H symbols and one Br symbol",
"molecule": "bromobutane",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
Answer: 9 bonds KEY
also accepted: 9 bonds
wrongValueDiagnostics
[
{
"value": 13,
"misconception": "you counted every bond in the molecule — the three C–C lines and the C–Br line are not C–H bonds",
"feedback": null
},
{
"value": 10,
"misconception": "you counted the C–Br bond as a C–H bond — bromine is not hydrogen: the count is 3 + 2 + 2 + 2 = 9",
"feedback": null
},
{
"value": 3,
"misconception": "you counted only the first carbon's hydrogens — all four carbons carry hydrogens",
"feedback": null
}
]
feedback
{
"keyExplanation": "Trace each line from a carbon to an H symbol: 3 + 2 + 2 + 2 = 9 C–H bonds. The three C–C lines and the C–Br line are bonds too, but not C–H bonds."
}
CMB-065 · medium · application · seq 11 · authored (full-reading pick across an internal triple bond, parallel to seed pool[14]) · mcq4
The figure shows the structural formula of a molecule logged in a synthesis lab's notebook. Which full reading of the structure is correct?
FIGURE (structural-formula · stimulus) — description: "four C symbols in a row: the second and third joined by three parallel lines (a triple bond), the first and fourth joined to them by single lines; the first… · molecule: "butyne (internal triple bond)" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four C symbols in a row: the second and third joined by three parallel lines (a triple bond), the first and fourth joined to them by single lines; the first and fourth carbons each bonded to three H symbols",
"molecule": "butyne (internal triple bond)",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
C₄H₆, containing one C≡C triple bond, two C–C single bonds, and six C–H bonds. KEY
C₄H₆, with three separate single bonds between the middle carbons.
C₄H₁₀, with every carbon carrying a full set of hydrogens.
The figure shows the structural formulas of four compounds, M, P, R, and T. Which compound contains a hydroxyl group?
FIGURE (structural-formula · stimulus) — description: "four small structures in a row: M is a plain six-carbon chain with only C–H and C–C bonds; P is a six-carbon chain whose end carbon is bonded to a Cl; R is … · molecule: "four-compound comparison" · style: "clean full structural formula matching the lesson figures' layout"raw spec
{
"figureRequired": true,
"figureShape": "stimulus",
"figureSpec": {
"figureType": "structural-formula",
"description": "four small structures in a row: M is a plain six-carbon chain with only C–H and C–C bonds; P is a six-carbon chain whose end carbon is bonded to a Cl; R is a six-carbon chain with a C=C double bond and only hydrogens attached; T is a six-carbon chain whose end carbon is bonded to an O, which is bonded to an H",
"molecule": "four-compound comparison",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
T KEY
M
P
R
CMB-067 · medium · application · seq 14 · authored (fresh instance rotation of the seed pool[19] pair-comparison; octane/octanol are taught in no scope corpus) · mcq4
Octane is an eight-carbon chain; octanol is the same chain with an –OH on its end carbon. A recipe calls for whichever liquid mixes better with water. Which choice is right, and why?
Octanol — its hydroxyl group hydrogen-bonds to water molecules. KEY
Octane — a plain frame pushes into water more readily than one carrying attachments.
Either one — the two share the same eight-carbon frame.
Octanol — the added oxygen weighs it down, and weightier liquids soak up water.
CMB-068 · medium · application · seq 15 · authored (feature-marks-the-acid pick; inverts the identification task) · mcq4
Four unlabeled carbon compounds arrive at a lab, and exactly one is acidic. Its structure should show which feature?
A carbon carrying BOTH a double-bonded O and an O–H — a carboxyl group. KEY
An O–H standing alone — the plain hydroxyl pattern.
An N bonded to two hydrogens at the end of the frame.
A carbon frame at least four carbons long.
CMB-068 · medium · application · seq 16 · authored (two-group discrimination on one frame; hydroxyl contrast is the taught rule-line distinction) · mcq4
Two compounds share the same four-carbon frame: one ends in a –COOH cluster, the other in a lone –OH. Which compound is acidic, and why?
The –COOH compound — the carboxyl group makes a compound acidic, while a lone O–H is a hydroxyl and does not. KEY
The –OH compound — a group with fewer oxygens in it always makes the sharper, stronger acid.
Both equally — any oxygen-bearing group makes a compound acidic.
Neither — four-carbon frames are too small to carry acidity.
A student finds a cluster at the end of a frame and calls it an amino group 'because hydrogens are attached to it.' The cluster is an O bonded to one H. What is the right correction?
An amino group is built on NITROGEN — an N bonded to two hydrogens; an O bonded to one H is a hydroxyl group instead. KEY
No correction is needed — every small cluster with hydrogens attached to it counts as an amino group.
It is an amino group whenever the cluster sits at the end of the frame.
It is a carboxyl group, because it contains oxygen.
CMB-069 · hard · transfer · seq 18 · authored (behavior-to-structure inference, the reverse read of seed pool[26]) · mcq4
A supplier's data sheet promises a compound that 'counteracts acidic residues.' Which structural feature should its formula drawing show?
A frame N bonded to two hydrogens — an amino group, the base-maker. KEY
A lone O–H on the frame.
A carbon carrying a double-bonded O and an O–H.
An extra-long carbon frame.
CMB-070 · hard · transfer · seq 19 · authored (two-group scan with the internal-O–H trap, parallel to the curated seeds; fresh real molecule) · mcq4
The figure shows the structural formula of a compound used in medicines that help control bleeding. Which functional groups does the molecule carry?
FIGURE (structural-formula · stimulus) — description: "a six-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second through fifth carbons each bonded to two hydrogens; the sixth carbon … · molecule: "6-aminohexanoic acid" · style: "clean full structural formula matching the lesson figures' layout"raw spec
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"figureRequired": true,
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"molecule": "6-aminohexanoic acid",
"style": "clean full structural formula matching the lesson figures' layout"
}
}
One carboxyl group and one amino group, with no hydroxyl group KEY
One carboxyl group, one amino group, and one hydroxyl group
Two amino groups and no carboxyl group
One hydroxyl group and one amino group, with no carboxyl group
CMB-070 · hard · transfer · seq 20 · authored (oxygen-tally error adjudication, parallel to seed pool[29]; two-hydroxyl key) · mcq4
A structure's two end carbons each carry a lone O–H, with no double-bonded O anywhere in the molecule. A student reports: 'one carboxyl group, since the molecule contains two oxygens.' What is the correct report?
Two hydroxyl groups — a carboxyl needs both oxygens on ONE carbon, one double-bonded, and no carbon here has that. KEY
The student is right — any two oxygens anywhere in one molecule add up to a single carboxyl group.
One hydroxyl group — two identical clusters merge into a single group.
One carboxyl group and one hydroxyl group — the two O–H clusters split the difference.
CMB-070 · medium · application · seq 21 · authored — UNSEEDED FRQ (prod_seeds = []); R14 written production per the blueprint seq-21 case; typed answer is plain words (V-T12: nothing typed requires sub/superscripts) · frq
The figure shows the structural formula of a compound found in celery and used in food flavorings.
FIGURE (structural-formula · stimulus) — description: "a four-carbon chain: the first carbon carrying a double-bonded O and an O–H; the second and third carbons each bonded to two hydrogens; the fourth carbon ca… · molecule: "succinic acid" · style: "clean full structural formula matching the lesson figures' layout"raw spec
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"molecule": "succinic acid",
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The figure shows the structural formula of a compound found in celery and used in food flavorings.
(a) List every functional group the molecule carries, with a count for each group.
(b) Justify each identification from the structure — say what is bonded to what — and state whether the two O–H clusters add hydroxyl groups, and why.
(c) Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Part a. List every functional group the molecule carries, with a count for each group.
Model: The molecule carries two functional groups, both the same kind: two carboxyl groups.
Part b. Justify each identification from the structure — say what is bonded to what — and state whether the two O–H clusters add hydroxyl groups, and why.
Model: Each end carbon carries a double-bonded O together with an O–H — the carboxyl pattern, once at each end. Neither O–H adds a hydroxyl group: each sits on a double-bonded-O carbon, so each is counted inside its own carboxyl, and the hydroxyl count is zero.
Part c. Predict ONE behavior of the compound and name the group responsible.
Write your answer in words; no chemical formulas or special symbols are needed.
Model: The carboxyl groups make the compound acidic.
Full model answer. (a) The molecule carries two functional groups, both the same kind: two carboxyl groups.
(b) Each end carbon carries a double-bonded O together with an O–H — the carboxyl pattern, once at each end. Neither O–H adds a hydroxyl group: each sits on a double-bonded-O carbon, so each is counted inside its own carboxyl, and the hydroxyl count is zero.
(c) The carboxyl groups make the compound acidic.