Acid hydrolysis
Water attack and proton transfers permit the ethoxy fragment to leave as ethanol. Re-forming the carbonyl produces butanoic acid on the other branch.
- Reagents
- Water; dilute acid catalyst
- Conditions
- Heat in aqueous acid; reversible hydrolysis
- Reaction class
- Acid hydrolysis
- Equation
- CH3CH2CH2COOCH2CH3 + H2O <=> CH3CH2CH2COOH + CH3CH2OH
Overview
Water attack and proton transfers permit the ethoxy fragment to leave as ethanol. Re-forming the carbonyl produces butanoic acid on the other branch.
Transformation
Ethyl butyrate → Butanoic acid
- Equation
- CH3CH2CH2COOCH2CH3 + H2O <=> CH3CH2CH2COOH + CH3CH2OH
- Reactants
- Ethyl butyrate + Water
- Products
- Butanoic acid + Ethanol
- 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
- Ethyl butanoate hydrolysis gives a four-carbon acid and a two-carbon alcohol.
- Limitations
- Both ester fragments form in the same reaction.
Related reactions
- Aldehyde oxidation: Butanal → Butanoic acid
The hydrated aldehyde is oxidised to a carboxyl group. All four starting carbon atoms remain together in butanoic acid.
- Esterification: Butanoic acid → Ethyl butyrate
Ethanol oxygen bonds to the acid carbonyl carbon, followed by proton transfer and water loss. The product joins a butanoyl fragment to an ethoxy group.
- 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
- 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.