What major product(s) will be yielded by the elimination reaction shown?

Question

BlackTom AI · Accepted Answer

Because the chloride is axial on the cyclohexane ring, only a trans‑diaxial (axial) β‑hydrogen can be removed in a concerted E2 process by methoxide, so elimination gives the alkene formed between the carbon bearing Cl and that specific adjacent carbon (product I).

1) Relevant concepts:
- E2 elimination requires an antiperiplanar arrangement of the leaving group and the β‑H for a concerted H removal / C=C formation.
- On cyclohexanes, “antiperiplanar” corresponds to trans‑diaxial geometry: an axial leaving group can only be antiperiplanar to axial hydrogens on neighboring carbons.
- Strong, unhindered base (OMe−) favors E2 over substitution.

2) Step‑by‑step reasoning:
- The substrate shows Cl in an axial position. Look at the two β‑carbons adjacent to the C–Cl. Each β‑carbon can have axial or equatorial hydrogens depending on the chair conformation.
- Only the axial β‑H that is trans‑diaxial to the axial Cl is properly aligned (antiperiplanar). Methoxide will abstract that axial β‑H.
- Electron flow: base removes that axial H → C–H electrons form the C=C between the two adjacent carbons → Cl− leaves simultaneously. This concerted E2 yields one regio/stereoisomeric alkene.

3) Intermediate steps (mechanistic arrows):
- OM e− : H(axial) —> form π bond between C(Cl) and that β‑C; C–Cl bond breaks → Cl−.

4) Why the correct answer is correct:
- Product I corresponds exactly to the alkene generated by deprotonation of the axial β‑H antiperiplanar to axial Cl. This is the only E2 path available without ring flip that would put Cl equatorial; a ring flip to allow other eliminations is higher energy or would still give the same predominant product.

5) Why the other options are incorrect:
- The other pictured alkenes require removal of equatorial β‑H (not antiperiplanar) or a different regiochemistry that the antiperiplanar requirement does not permit under E2. They are therefore not formed as the major product.

6) Conclusion:
- The major product is I, matching the given correct answer.

What major product(s) will be yielded by the elimination reaction shown?Single choice

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