JEE Main Chemistry question

What is the final product of the following reaction? A ring bearing both –COCH₃ and –COOH (ortho to each other) --CH₃OH, -H₂O--> ?

(A)The corresponding cyclic lactone/lactol formed by intramolecular transesterification-type cyclization with the methyl ketone converted to a cyclic hemiketal-esterCorrect
(B)The simple open-chain methyl ester (methyl ester of the acid, ketone untouched)
(C)A fully methylated bis-ether product
(D)An unreacted mixture

Answer: (A)

Solution

With an ortho-positioned ketone and carboxylic acid on the same ring, methanol under acid-catalyzed conditions can esterify the acid; but given the ortho relationship, intramolecular cyclization (the ester oxygen or an enol oxygen of the ketone reaching back to interact intramolecularly) is strongly favoured over

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Question ID VK-149387