JEE Main Chemistry question

Which of the following carboxylic acids undergoes decarboxylation easily?

(A)C₆H₅–CO–CH₂–COOH (a β-keto acid)Correct
(B)C₆H₅–CO–COOH (an α-keto acid)
(C)C₆H₅COOH (benzoic acid)
(D)C₆H₅CH₂COOH (phenylacetic acid)

Answer: (A)

Solution

β-Keto acids (carboxyl and ketone carbonyl separated by one carbon) decarboxylate readily on mild heating via a favourable six-membered cyclic transition state involving the ketone's own carbonyl oxygen, directly expelling CO₂ and forming an enol that tautomerizes to

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Question ID VK-149470