Fischer esterification
Abstract
The Fischer esterification is a synthetic method used to prepare esters from a carboxylic acid and an alcohol under acidic catalysis. Because the reaction is an equilibrium process, several strategies can be employed to shift the equilibrium toward ester formation, such as continuous removal of water using a Dean-Stark apparatus.
Keywords
Carboxylic acid, Alcohol, Ester,
Category
Carboxylic acid, Alcohol
Mechanism
First, the carbonyl oxygen of the carboxylic acid is protonated under acidic conditions, increasing the electrophilicity of the carbonyl carbon. The alcohol then acts as a nucleophile and attacks the activated carbonyl carbon, forming a tetrahedral intermediate. Following a proton transfer step, the intermediate undergoes elimination of a water molecule. Finally, deprotonation regenerates the acid catalyst and gives the desired ester.
