Topic overview

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The reaction applies to acyl chlorides, anhydrides, esters, carboxylic acids, amides, and carboxylates. Their relative reactivity generally follows leaving-group ability: acyl chlorides and anhydrides are more reactive than esters and acids, while amides and carboxylates are less reactive. Carbonyl electrophilicity also changes with substituents and reaction conditions: protonation activates the carbonyl, while basic conditions can make the nucleophile more reactive. These principles help explain transformations such as hydrolysis, esterification, transesterification, and amide formation. The broader lesson connects the shared mechanism to these reactions and to selected preparations and conversions of acyl derivatives.