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Chemistry · Ch 11 — Hydroxy Compounds and Ethers

Esterification of Alcohols

11.6.4

Esterification of Alcohols

In the presence of an acid catalyst, an alcohol reacts with a carboxylic acid to form an ester and water (Fischer esterification) -- e.g. ethanol + ethanoic acid, with H+, gives ethyl ethanoate + H2O. The reaction is reversible and is driven toward the ester by removing water as it forms or by using an excess of one reactant. The order of reactivity of alcohols toward esterification follows primary > secondary > tertiary, the reverse of their reactivity in acid-catalysed dehydration, since a bulkier alcohol hinders the nucleophilic attack of its oxygen …