Acid hydrolysis
Ethyl acetate and water react reversibly to form ethanoic acid and ethanol.
- Reagents
- Water; dilute acid catalyst
- Conditions
- Heat under reflux in aqueous acid
- Reaction class
- Acid hydrolysis
- Equation
- CH3COOCH2CH3 + H2O <=> CH3COOH + CH3CH2OH
Overview
Ethyl acetate and water react reversibly to form ethanoic acid and ethanol.
Transformation
- Equation
- CH3COOCH2CH3 + H2O <=> CH3COOH + CH3CH2OH
- Reactants
- Ethyl acetate + Water
- Products
- Ethanoic acid + Ethanol
- Reagents
- Water; dilute acid catalyst
- Environment
- Heat under reflux in aqueous acid
- Reaction class
- Acid hydrolysis
- Mechanism
- acid-catalysed ester hydrolysis
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Ethyl acetate (ethyl ethanoate).
- Limitations
- Ethanol is the other product. Reversible; alkaline hydrolysis gives ethanoate rather than the free acid.
Related reactions
- Oxidation: Ethanol → Ethanoic acid
Ethanol is oxidised to ethanoic acid.
- Oxidation: Ethanal → Ethanoic acid
Ethanal is oxidised to ethanoic acid.
- Esterification: Ethanoic acid → Ethyl acetate
Ethanoic acid and ethanol combine reversibly to form ethyl acetate and water.
- Esterification: Ethanol → Ethyl acetate
Ethanoic acid and ethanol combine reversibly to form ethyl acetate and water.
- Acid hydrolysis: Ethyl acetate → Ethanol
Ethyl acetate and water react reversibly to form ethanoic acid and ethanol.
- Amide hydrolysis: Acetamide → Ethanoic acid
Acid activates the amide carbonyl for water addition. Proton transfer makes nitrogen a better leaving group before C-N cleavage; the acyl fragment becomes ethanoic acid and the nitrogen ends as ammonium.
- Acid hydrolysis: Methyl acetate → Ethanoic acid
Water adds to the protonated ester carbonyl. Proton transfer allows methanol to leave as the carbonyl reforms, producing the acid and alcohol together.
References
- Hydrolysing estersJim Clark · Chemguide · 2016
Named molecular examples and reaction scope, checked 2026-09-08.