Reactions of esters

thumb|upright=1.7|Generic hydrolysis reaction. (The 2-way yield symbol indicates a chemical equilibrium in which hydrolysis and condensation are reversible.) Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution and elimination reactions in which water is the nucleophile.

Saponification is a process of cleaving esters into carboxylate salts and alcohols by the action of aqueous alkali. Typically aqueous sodium hydroxide solutions are used. It is an important type of alkaline hydrolysis. When the carboxylate is a long chain, its salt is called a soap. The saponification of ethyl acetate gives sodium acetate and ethanol:

Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile. Bases catalyze the reaction by removing a proton from the alcohol, thus making it more nucleophilic. The reaction can also be accomplished with the help of enzymes, particularly lipases (one example is the lipase E.C.3.1.1.3).