The compound shown contains two different carbonyl groups. On treatment with one equivalent of sodium borohydride in ethanol, which group is reduced?

AOnly the ketone C=O
BOnly the ester C=O
CBoth C=O groups
DNeither group

Answer: A

Methyl 4-acetylbenzoate has a ketone and an ester. Sodium borohydride is a mild hydride donor that reduces aldehydes and ketones but is too weak to reduce esters, so only the ketone C=O is converted to a secondary alcohol.

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