Base hydrolysis of an amide yields which pair of products?

Master NCEA Level 3 Organic Chemistry Reaction Schemes. Prepare with multiple choice questions, complete with hints and detailed explanations. Ace your exam with our comprehensive tools!

Multiple Choice

Base hydrolysis of an amide yields which pair of products?

Base hydrolysis of an amide (saponification) cleaves the C–N bond and, in a basic medium, yields a carboxylate salt and an amine. The hydroxide attacks the carbonyl to form a tetrahedral intermediate, which collapses to give the carboxylate and release the nitrogen as an amine. Because the environment is strongly basic, the carboxyl group is present as the deprotonated carboxylate, not a free carboxylic acid, and the nitrogen product remains as a neutral amine rather than being protonated to ammonium. That’s why the correct pair is carboxylate salt and amine. Under acidic hydrolysis you’d get carboxylic acid and ammonium, and other options don’t reflect amide hydrolysis under basic conditions (ester hydrolysis gives alcohol and acid or its salt, not an amine with a carboxylate).

Base hydrolysis of an amide (saponification) cleaves the C–N bond and, in a basic medium, yields a carboxylate salt and an amine. The hydroxide attacks the carbonyl to form a tetrahedral intermediate, which collapses to give the carboxylate and release the nitrogen as an amine. Because the environment is strongly basic, the carboxyl group is present as the deprotonated carboxylate, not a free carboxylic acid, and the nitrogen product remains as a neutral amine rather than being protonated to ammonium.

That’s why the correct pair is carboxylate salt and amine. Under acidic hydrolysis you’d get carboxylic acid and ammonium, and other options don’t reflect amide hydrolysis under basic conditions (ester hydrolysis gives alcohol and acid or its salt, not an amine with a carboxylate).

More practice questions