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Also known as: Fischer-Speier Esterification
Discovered by Emil Fischer (1895)
Acid-catalyzed condensation of a carboxylic acid with an alcohol to form an ester. The reaction is an equilibrium, so water removal (Dean-Stark trap) or excess alcohol drives it to completion.
Protonation of the carboxylic acid carbonyl oxygen by H⁺, activating it toward nucleophilic attack.
Nucleophilic addition of the alcohol to the protonated carbonyl carbon, forming a tetrahedral intermediate.
Tetrahedral intermediate
Proton transfer within the tetrahedral intermediate, protonating one of the OH groups to make it a better leaving group (water).
Loss of water and deprotonation to give the ester product.
Equilibrium — remove water to drive forward
Acetic acid + Ethanol
H₂SO₄ cat., reflux
Ethyl acetate
Benzoic acid + Methanol
HCl cat., reflux
Methyl benzoate
One of the most common ester syntheses. Esters are used as solvents, fragrances, and pharmaceutical intermediates.