JEE Main Chemistry question

Which of the following carboxylic acids is not reduced to the corresponding 1° alcohol by LiAlH₄?

(A)BrCH₂CH₂CH₂COOHCorrect
(B)Cyclohexane carboxylic acid
(C)(Z)-CH₃CH=CHCH₂COOH
(D)CH₃CH(CH₃)CH₂COOH

Answer: (A)

Solution

LiAlH₄ chemoselectively reduces the carboxylic acid group to a primary alcohol in all four of these substrates (it is compatible with an alkyl bromide only in the sense that it may also reduce/displace some halides, with an alkene, and with a branched alkyl chain) — so in the strict sense all four acids ARE reduced to

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Question ID VK-149456