Esterification
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.
- Reagents
- Ethanoic acid; H2SO4 catalyst
- Conditions
- Warm with acid catalyst; reversible equilibrium
- Reaction class
- Esterification
- Equation
- CH3COOH + CH3CH2CH2CH2OH <=> CH3COOCH2CH2CH2CH3 + H2O
Overview
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.
Transformation
- Equation
- CH3COOH + CH3CH2CH2CH2OH <=> CH3COOCH2CH2CH2CH3 + H2O
- Reactants
- Ethanoic acid + Butan-1-ol
- Products
- Butyl acetate + Water
- Reagents
- Ethanoic acid; H2SO4 catalyst
- Environment
- Warm with acid catalyst; reversible equilibrium
- Reaction class
- Esterification
- Mechanism
- acid-catalysed nucleophilic acyl substitution
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Butan-1-ol supplies the four-carbon alkoxy group.
- Limitations
- Ethanoic acid is required. Butyl acetate and ethyl butyrate share a molecular formula but split into different fragments on hydrolysis.
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.
- Acid hydrolysis: Butyl acetate → Butan-1-ol
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.
References
- Organic Chemistry: Reactions of Carboxylic AcidsJohn McMurry · OpenStax Organic Chemistry · 2023
Checked 2026-09-16. Supports the reaction pattern and mechanistic explanation; named examples apply that scope to existing molecular records without claimed experimental yields.