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
- 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
- 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: 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.
- 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.
- 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 → Butanoic acid
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.