Esterification
Ethanoic acid and ethanol combine reversibly to form ethyl acetate and water.
- Reagents
- Ethanoic acid; H2SO4 catalyst
- Conditions
- Warm; reversible acid-catalysed equilibrium
- Reaction class
- Esterification
- Equation
- CH3COOH + CH3CH2OH <=> CH3COOCH2CH3 + H2O
Overview
Ethanoic acid and ethanol combine reversibly to form ethyl acetate and water.
Transformation
- Equation
- CH3COOH + CH3CH2OH <=> CH3COOCH2CH3 + H2O
- Reactants
- Ethanoic acid + Ethanol
- Products
- Ethyl acetate + Water
- Reagents
- Ethanoic acid; H2SO4 catalyst
- Environment
- Warm; reversible acid-catalysed equilibrium
- Reaction class
- Esterification
- Mechanism
- acid-catalysed esterification
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Ethanol plus ethanoic acid.
- Limitations
- Ethanoic acid is a required co-reactant. Both starting compounds contribute carbon atoms to the ester.
Related reactions
- Iodoform reaction: Ethanol → Triiodomethane products
Ethanol is oxidised and cleaved by alkaline iodine to give triiodomethane and methanoate.
- Partial oxidation: Ethanol → Ethanal
Ethanol is oxidised to ethanal.
- Oxidation: Ethanol → Ethanoic acid
Ethanol is oxidised to ethanoic acid.
- Reduction: Ethanal → Ethanol
Ethanal is reduced to ethanol.
- Esterification: Ethanoic acid → Ethyl acetate
Ethanoic acid and ethanol combine reversibly to form ethyl acetate and water.
- Acid hydrolysis: Ethyl acetate → Ethanoic acid
Ethyl acetate and water react reversibly to form ethanoic acid and ethanol.
- Acid hydrolysis: Ethyl acetate → Ethanol
Ethyl acetate and water react reversibly to form ethanoic acid and ethanol.
- Hydration: Ethene → Ethanol
Ethene gives ethanol through hydration.
- Dehydration: Ethanol → Ethene
Ethanol gives ethene through dehydration.
- Intermolecular dehydration: Ethanol → Diethyl ether
Protonation turns one ethanol OH group into a better leaving group. The oxygen of another ethanol molecule displaces water, and deprotonation gives diethyl ether; stronger dehydration conditions instead favour ethene.
- Hydrolysis: Bromoethane → Ethanol
Hydroxide attacks the saturated carbon bearing bromine while the C-Br bond breaks. This primary-substrate SN2 route replaces bromide with OH and preserves both carbon atoms; aqueous conditions favour this branch over elimination.
- Acid hydrolysis: Ethyl butyrate → Ethanol
Water attack and proton transfers permit the ethoxy fragment to leave as ethanol. Re-forming the carbonyl produces butanoic acid on the other branch.
References
- Making estersJim Clark · Chemguide · 2016
Named molecular examples and reaction scope, checked 2026-09-08.