Benjamin's Chemistry

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  • Carboxylic Acids
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  • Hydrolysis of Esters
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Hydrolysis

 

The opposite of esterification, therefore the process by which one would react an ester with water to return it to the carboxylic acid and acid. The hydrolysis of the ester can be catalysed using either an acid or alkali.

If using an acid catalyst, the reaction is reversible and as such the hydrolysis is is imperfect as some ester will still be present in the equilibrium mixture.

                                                           H+

      Ester     +           Water         is in equilibrium with         Carboxylic acid     +      Alcohol

 

or                                                            

                                                                  H+

       RCOOCR3      +      H2O      is in equilibrium with     RCOOH         +     R3COH 

 

Using an alkali catalyst instead produces a non-reversible reaction which fully hydrolyses the ester into the salt of the acid and the alcohol. The general reaction is written below, a specific example for hydrolysis of ethyl ethanoate using NaOH (aq) is shown beneath this. 

     Ester     +      Alkali           →      Salt     +      Alcohol

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