Cyclopropyl–C –CH_3 (X, 1 mol) [ H _3 O ^+] HCO _3 H A [ CH _3 COOH ] CrO _3 B Aq. KMnO _4 C. Identify the row (A, B, C) that correctly completes this sequence.

JEE Main Chemistry question

Cyclopropyl–CC–CH (, 1 mol) . Identify the row (A, B, C) that correctly completes this sequence.

(A) = cyclopropyl–CH(OH)–CO–CH (an acyloin); = cyclopropyl–CO–CO–CH (a 1,2-diketone); = cyclopropanecarboxylic acid + CHCOOHCorrect
(B) = cyclopropyl–C(OH)=CH–CH (an enol, unisolated); = cyclopropyl–CO–CH–CH; = cyclopropanecarboxylic acid only
(C) = cyclopropyl–CH–CO–CH; = cyclopropyl–CH–COOH; = cyclopropylacetic acid + CO
(D)None of these

Answer: (A)

Solution

Peracid (HCOH)-mediated hydration of the internal alkyne under acidic aqueous workup gives the -hydroxyketone (acyloin) . CrO/AcOH oxidises the remaining secondary alcohol of to a 1,2-diketone, . Aqueous

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Question ID VK-142474