Acid-catalyzed hydrolysis of an ester produces which two products?

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Multiple Choice

Acid-catalyzed hydrolysis of an ester produces which two products?

Acid-catalyzed ester hydrolysis yields a carboxylic acid and an alcohol. The carbonyl oxygen is protonated, making the carbonyl carbon more electrophilic so water can attack. A tetrahedral intermediate forms, then proton transfers convert the leaving group into a good ROH, and collapse releases the alcohol while generating the carboxylic acid. The acid catalyst is regenerated at the end. So the two products are the alcohol derived from the ester’s alkoxy part and the carboxylic acid from the acyl part. If the reaction were under basic conditions, you’d instead get a carboxylate salt rather than the free carboxylic acid.

Acid-catalyzed ester hydrolysis yields a carboxylic acid and an alcohol. The carbonyl oxygen is protonated, making the carbonyl carbon more electrophilic so water can attack. A tetrahedral intermediate forms, then proton transfers convert the leaving group into a good ROH, and collapse releases the alcohol while generating the carboxylic acid. The acid catalyst is regenerated at the end. So the two products are the alcohol derived from the ester’s alkoxy part and the carboxylic acid from the acyl part. If the reaction were under basic conditions, you’d instead get a carboxylate salt rather than the free carboxylic acid.

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