An ester reacts with ammonia in alcohol to form which products?

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Multiple Choice

An ester reacts with ammonia in alcohol to form which products?

The key idea is nucleophilic acyl substitution: ammonia acts as the nucleophile and replaces the alkoxy group of the ester. When ammonia attacks the carbonyl carbon, the tetrahedral intermediate collapses and the alkoxy group leaves as an alcohol in the alcoholic solvent. The result is the amide with NH2 attached to the carbonyl and the alcohol corresponding to the alkoxy part of the original ester. Because ammonia donates one hydrogen, the amide formed is primary (R-CO-NH2). If a secondary or tertiary amine were involved, a secondary or tertiary amide would form instead; water would hydrolyze the ester to a carboxylic acid rather than an amide; and forming an ether would require a different reaction pathway. So the products are a primary amide and the corresponding alcohol.

The key idea is nucleophilic acyl substitution: ammonia acts as the nucleophile and replaces the alkoxy group of the ester. When ammonia attacks the carbonyl carbon, the tetrahedral intermediate collapses and the alkoxy group leaves as an alcohol in the alcoholic solvent. The result is the amide with NH2 attached to the carbonyl and the alcohol corresponding to the alkoxy part of the original ester. Because ammonia donates one hydrogen, the amide formed is primary (R-CO-NH2). If a secondary or tertiary amine were involved, a secondary or tertiary amide would form instead; water would hydrolyze the ester to a carboxylic acid rather than an amide; and forming an ether would require a different reaction pathway. So the products are a primary amide and the corresponding alcohol.

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