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Multiple Choice

Basic hydrolysis of an amide under basic conditions yields which products?

Basic hydrolysis of an amide involves hydroxide attacking the carbonyl carbon, forming a tetrahedral intermediate that collapses to give the carboxylate and the amine fragment. In basic conditions, the carboxyl group is kept deprotonated, so you obtain a carboxylate salt rather than a free carboxylic acid. The nitrogen from the amide is released as an amine (for a primary amide this is ammonia; for substituted amides it’s the corresponding amine). Therefore the typical products are a carboxylate salt and an amine.

Basic hydrolysis of an amide involves hydroxide attacking the carbonyl carbon, forming a tetrahedral intermediate that collapses to give the carboxylate and the amine fragment. In basic conditions, the carboxyl group is kept deprotonated, so you obtain a carboxylate salt rather than a free carboxylic acid. The nitrogen from the amide is released as an amine (for a primary amide this is ammonia; for substituted amides it’s the corresponding amine). Therefore the typical products are a carboxylate salt and an amine.