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JEE Main Chemistry question

ChemistryAldehydes, Ketones and Carboxylic AcidsJEE Main

A keto ester (A) with molecular formula C₆H₁₀O₃, on treatment with NaOH + I₂, does not give iodoform but on boiling with dilute KOH gives a compound (B) with molecular formula C₄H₅O₃K, which upon acidification followed by heating undergoes decarboxylation to acetone. The keto ester A is

Answer: (B)

Solution

A decarboxylates to acetone, so its hydrolysis product B is a β-keto acid of the form CH₃COCH₂COOH (acetoacetic acid, which readily loses CO₂ on heating to give acetone). Working backward, A must be the corresponding ester of this β-keto acid; with molecular formula C₆H₁₀O₃ (matching ethyl acetoacetate,

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Question ID VK-149372