JEE Main Chemistry question

Chemistry Organic Oxidation & Reduction Reactions JEE Main

The appropriate reagent for the transformation of a ring-fused hydroxy-methyl ketone (HO– and –COCH₃ on a cyclohexane ring) to the corresponding hydroxy-ethyl compound (HO– and –CH₂CH₃) is

(A)Zn(Hg), HClCorrect
(B)NH₂NH₂, OH⁻
(C)H₂/Ni
(D)NaBH₄

Answer: (A)

Solution

Full reduction of the ketone carbonyl to a CH₂ group (giving the ethyl substituent, –COCH₃ → –CH₂CH₃) while leaving the ring's own hydroxyl group intact is best achieved by Clemmensen reduction (Zn–Hg/conc. HCl); NaBH₄ would only

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Question ID VK-149349