JEE Main Chemistry question

Which of the following will produce only one product on reduction with LiAlH₄?

(A)CH₃OCOCH₃
(B)CH₃CH₂OCOCH₂CH₃
(C)CH₃CH₂OCOCH₃Correct
(D)CH₃CH₂OCOCH₂CH₂CH₃

Answer: (C)

Solution

LiAlH₄ cleaves an ester RCOOR′ into two alcohols: RCH₂OH (from the acyl portion) and R′OH (from the alkoxy portion); a single alcohol product results only when these two happen to be the same compound. Ethyl acetate, CH₃CH₂OCOCH₃, reduces its acetyl (CH₃CO–) portion to ethanol (CH₃CH₂OH) and

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Question ID VK-149330