Acid hydrolysis
Hydrolysis breaks the acyl-to-oxygen connection after water addition and proton transfer. The original butyl group stays attached to oxygen and leaves as butan-1-ol.
- Reagents
- Water; dilute acid catalyst
- Conditions
- Heat in aqueous acid; reversible hydrolysis
- Reaction class
- Acid hydrolysis
- Equation
- CH3COOCH2CH2CH2CH3 + H2O <=> CH3COOH + CH3CH2CH2CH2OH
Overview
Hydrolysis breaks the acyl-to-oxygen connection after water addition and proton transfer. The original butyl group stays attached to oxygen and leaves as butan-1-ol.
Transformation
- Equation
- CH3COOCH2CH2CH2CH3 + H2O <=> CH3COOH + CH3CH2CH2CH2OH
- Reactants
- Butyl acetate + Water
- Products
- Ethanoic acid + Butan-1-ol
- Reagents
- Water; dilute acid catalyst
- Environment
- Heat in aqueous acid; reversible hydrolysis
- Reaction class
- Acid hydrolysis
- Mechanism
- acid-catalysed ester hydrolysis
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- The butoxy portion returns to butan-1-ol; ethanoic acid is the other product.
- Limitations
- This is the alcohol-product view of one ester-hydrolysis reaction, not selective production of a lone alcohol.
Related reactions
- Controlled oxidation: Butan-1-ol → Butanal
Oxidation removes hydrogen from the O-H bond and the OH-bearing carbon to form C=O. Separating butanal as it forms limits its further oxidation.
- Carbonyl reduction: Butanal → Butan-1-ol
Hydride adds to the aldehyde carbon and the carbonyl oxygen becomes an alkoxide. Protonation completes the return to butan-1-ol.
- Esterification: Butan-1-ol → Butyl acetate
The alcohol oxygen attacks an activated ethanoic-acid carbonyl. The four-carbon chain remains on oxygen while the two-carbon acetate fragment supplies the carbonyl.
References
- Organic Chemistry: Chemistry of EstersJohn McMurry · OpenStax Organic Chemistry · 2023
Distinguishes reversible acid-catalysed ester hydrolysis from alkaline saponification, which gives a carboxylate ion until a separate acidification step.