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NEET 2023 Phase 2 · ChemistryCarbonyl reductionPrevious Year Question

The major product formed in the following conversion is: A cyclopentanone bearing a (2-oxopropyl) side chain treated with (i) , then (ii) , heat.

Answer: (C) (C). \textbf{Answer:} (C) cyclopentene ring (endocyclic ) bearing an internal prop-1-enyl side chain \textbf{Solution:} reduces both carbonyl groups (the ring ketone and the side-chain ketone) to secondary alcohols, giving a diol.

NEET 2023 Phase 2 Chemistry question — The major product formed in the following conversion is: A cyclopentanone bearing a…
  1. A.(A)
  2. B.(B)
  3. C.(C)✓
  4. D.(D)

Correct Answer

(C) (C)

Solution & Explanation

\textbf{Answer:} (C) cyclopentene ring (endocyclic ) bearing an internal prop-1-enyl side chain \textbf{Solution:} reduces both carbonyl groups (the ring ketone and the side-chain ketone) to secondary alcohols, giving a diol. On heating with , each alcohol undergoes acid-catalysed E1 dehydration to the more substituted (Saytzeff) alkene: the ring gives an endocyclic cyclopentene double bond and the side-chain gives an internal prop-1-enyl double bond. The major product is this doubly dehydrated diene.

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