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Saponification

  • Page ID
    5920
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    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 be 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 \(\PageIndex{1}\)
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    Mechanism

    Step 1: Nucleophilic attack by hydroxide

    3.jpg

    Step 2: Leaving group removal

    4a.jpg

    Step 3: Deprotonation

    5.jpg

    Contributors


    Saponification is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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