Discussion
In the reaction
the product formed is
- A.
- B.
- C.
- D.
Answer: A
The product is 1-acetylcyclopentene (A).
6-Oxoheptanal has a methyl ketone at one end and an aldehyde at the other. In base it undergoes an intramolecular aldol condensation. The more electrophilic carbonyl, the aldehyde, is attacked, and the enolate that can reach it to close a five-membered ring is the one formed at the ketone's internal CH2. The aldol then dehydrates to give a double bond conjugated with the ketone: 1-acetylcyclopentene.
B is the other five-membered aldol, made by an aldehyde enolate attacking the less electrophilic ketone, which is the minor path. C would need the terminal methyl enolate to close a seven-membered ring, which is slower than five-membered closure. D contains no oxygen at all, while an aldol condensation keeps the ketone, so it cannot form here.
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