Amide hydrolysis under acidic conditions yields what?

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Multiple Choice

Amide hydrolysis under acidic conditions yields what?

Acidic hydrolysis of an amide converts the C–N bond into a carboxyl group and releases the amine as its conjugate acid. In acid, the carbonyl is protonated to make it more electrophilic, water adds to form a tetrahedral intermediate, and after proton transfers the amide nitrogen leaves as ammonium. This leaves behind a carboxylic acid and NH4+. So the products are a carboxylic acid and an ammonium salt. Under basic conditions, you’d instead get a carboxylate salt and ammonia, which is why the acid case gives the ammonium salt rather than ammonia or other carbonyl fragments.

Acidic hydrolysis of an amide converts the C–N bond into a carboxyl group and releases the amine as its conjugate acid. In acid, the carbonyl is protonated to make it more electrophilic, water adds to form a tetrahedral intermediate, and after proton transfers the amide nitrogen leaves as ammonium. This leaves behind a carboxylic acid and NH4+. So the products are a carboxylic acid and an ammonium salt. Under basic conditions, you’d instead get a carboxylate salt and ammonia, which is why the acid case gives the ammonium salt rather than ammonia or other carbonyl fragments.

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