22. Carboxylic Acid Derivatives: NAS
Acid-Catalyzed Ester Hydrolysis
4:07 minutes
Problem 21-23
Textbook Question
Textbook QuestionThe mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, except that the nitrile is first protonated, activating it toward attack by a weak nucleophile (water). Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzed hydrolysis of benzonitrile to benzamide.
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