Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

The reduction of cyclohexanone with $NaBH_4$ produces

Options:

Cyclohexanol

Cyclohexene

Cyclohexane-1,2-diol

Cyclohexane carboxylic acid

Correct Answer:

Cyclohexanol

Explanation:

The correct answer is Option (1) → Cyclohexanol

Reason:

NaBH₄ is a mild reducing agent that selectively reduces the carbonyl group (C=O) of ketones to a secondary alcohol (–CHOH).

Reaction: Cyclohexanone → cyclohexanol (secondary alcohol)

No effect on C=C bonds or further reduction.

Why others are wrong:

  • Cyclohexene: Requires dehydration or strong reducing conditions (e.g., Clemmensen/Wolff-Kishner gives cyclohexane).
  • Cyclohexane-1,2-diol: Comes from dihydroxylation of cyclohexene (e.g., with OsO₄ or cold KMnO₄).
  • Cyclohexane carboxylic acid: Not a reduction product.