Acid & Alkaline Hydrolysis of Esters
Hydrolysis of Esters - Acid
- The reverse of the esterification reaction is called hydrolysis
- Ester hydrolysis is a useful reaction for creating biodegradable plastics
- Esters can be hydrolysed to reform the carboxylic acid and alcohol or salts of carboxylic acids by using either dilute acid (e.g. sulfuric acid) or alkali (e.g. sodium hydroxide) and heat
- When an ester is heated under reflux with acid an equilibrium mixture is established, meaning that the hydrolysis reaction is not complete
Ester hydrolysis by dilute acid is a reversible reaction forming carboxylic acid and alcohol
Hydrolysis of Esters - Alkaline
- However, heating the ester under reflux with dilute alkali (e.g. sodium hydroxide) is an irreversible reaction as the ester is fully hydrolysed and the reaction goes to completion
- The carboxylic acid produced reacts with excess alkali to form a carboxylate salt and alcohol
- The sodium carboxylate salt requires further acidification to turn into a carboxylic acid
- The sodium carboxylate (-COO-) ion needs to get protonated by an acid (such as HCl) to form the carboxylic acid (-COOH)
Ester hydrolysis by dilute alkali is an irreversible reaction forming a sodium carboxylate salt and alcohol
Table showing differences in Hydrolysis of Esters
Worked example
Name the products and write equations for the following hydrolysis reaction:
- Ethyl ethanoate with hot dilute sulfuric acid solution
- Methyl propanoate by hot sodium hydroxide solution
Answer:
Answer 1: Ethanoic acid and ethanol
CH3COOCH2CH3 + H2O ⇌ CH3COOH + CH3CH2OH
Answer 2: Sodium propanoate and methanol
CH3CH2COOCH3 + NaOH → CH3CH2COONa + CH3OH