Ester Hydrolysis
Ester hydrolysis is a reaction that involves splitting an ester bond using water, catalyzed by either an acid or a base. There are two types of ester hydrolysis: acidic hydrolysis and basic hydrolysis, also known as (saponification). The choice between acidic and basic hydrolysis depends on the specific reaction conditions and the desired products.
Ester Hydrolysis with NaOH
Ester hydrolysis with NaOH, also known as base-catalyzed ester hydrolysis, is the reaction of an ester with water under a basic medium. In this process, an ester is heated under reflux with dilute NaOH to yield carboxylate salt and alcohol. This reaction is also known as saponification, as it is used to synthesize soap.
Example of Basic hydrolysis (Saponification):
C6H5COOCH3 + NaOH → C6H5COONa + CH3OH
Mechanism of Hydrolysis of Ester with NaOH
When an ester is hydrolyzed with sodium hydroxide (NaOH), the process involves a two-step mechanism known as nucleophilic acyl substitution. The steps involved in the mechanism of ester hydrolysis with NaOH are:
- Nucleophilic Attack: The hydroxide ion (OH–) from NaOH acts as a nucleophile and attacks the electrophilic carbon of the ester’s carbonyl group, breaking the π bond and forming a tetrahedral intermediate.
- Elimination: The tetrahedral intermediate undergoes elimination, forming a carboxylate ion and an alcohol.
- Acid-Base Reaction: The carboxylate ion is then protonated by the NaOH, yielding the carboxylate salt.
This reaction is one-way rather than reversible, and the products are easier to separate than acid-catalyzed ester hydrolysis.
Hydrolysis of EstersEster Hydrolysis with NaOH
Ester hydrolysis is breaking down an ester into its constituent carboxylic acid and alcohol this takes place in an acidic or basic medium. The mechanisms of acid-catalyzed ester hydrolysis differ, with base-catalyzed hydrolysis being irreversible.
In this article, we look into what ester is, the hydrolysis of ester, its reaction, mechanism, application, etc.
Table of Content
- What is an Ester?
- What is Hydrolysis?
- Ester Hydrolysis
- Ester Hydrolysis with H2SO4
- Hydrolyzing Ester to Make Soap
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