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Chemistry LibreTexts

22.10: Reactions of Esters

  • Page ID
    28421
  • Esters can be cleaved back into a carboxylic acid and an alcohol by reaction with water and a catalytic amount of acid.

    General Reaction

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    Example 1:
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    Mechanism

    1) Protonation of the Carbonyl

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    2) Nucleophilic attack by water

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    3) Proton transfer

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    4) Leaving group removal

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    The resulting carbonyl is deprotonated by water to reform H3O+ and yield the neutral carboxylic acid.

    Esters can be cleaved back into a carboxylic acid and an alcohol by reaction with water and a base

    The reaction is called a saponification from the Latin sapo which means soap. The name comes from the fact that soap used to me made by the ester hydrolysis of fats. Due to the basic conditions a carboxylate ion is made rather than a carboxylic acid.

    General reaction

    1.jpg

    Example 1:
    2.jpg

    Mechanism

    1) Nucleophilic attack by hydroxide

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    2) Leaving group removal

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    3) Deprotonation

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