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Answer :
The correct answer is d) acid chloride. The reaction of an acid chloride with a Grignard reagent followed by hydrolysis produces a ketone, unlike esters, which yield tertiary alcohols after reacting twice with Grignard reagents. Therefore, option (d) acid chloride is the correct answer.
The reaction of acid chlorides with Grignard reagents followed by hydrolysis yields a ketone. This is due to the highly reactive nature of acid chlorides, which allows for the addition of two equivalents of a Grignard reagent. In the first step, the Grignard reagent performs a nucleophilic acyl substitution, displacing the chloride ion and forming a ketone intermediate. Unlike with esters, where the initially formed ketone undergoes a further reaction with a second molecule of Grignard reagent to yield a tertiary alcohol, with acid chlorides, the hydrolysis step follows directly after the ketone formation.
On the other hand, the reaction of Grignard reagents with esters forms a tertiary alcohol after hydrolysis because the Grignard reagent adds twice, forming a ketone intermediate that is further reacted with another molecule of the Grignard reagent. For other compounds, such as aldehydes or nitriles, the reactions with Grignard reagents also proceed differently. Therefore, option (d) acid chloride is the correct answer.
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