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Conversion of carboxylic acids to acid chlorides

  • Page ID
    5437
  • [ "article:topic", "Author tag:Farmer", "showtoc:no" ]

    Carboxylic acids react with Thionyl Chloride (\(SOCl_2\)) to form acid chlorides. During the reaction the hydroxyl group of the carboxylic acid is converted to a chlorosulfite intermediate making it a better leaving group. The chloride anion produced during the reaction acts a nucleophile.

    General Reaction

     

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    Example

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    Mechanism

    1) Nucleophilic attack on Thionyl Chloride

     

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    2) Removal of Cl leaving group

     

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    3) Nucleophilic attack on the carbonyl

     

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    4) Leaving group removal

     

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    5) Deprotonation

     

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    Contributors

    Prof. Steven Farmer (Sonoma State University)