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14.5 Acid Chloride Formation

  • Page ID
    25573
  • 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)

    Further Reading

    MasterOrganic Chemistry

    Thionyl Chloride

    Khan Academy

    Acid Chloride Formation

    Chemtube3D

    Acid Chloride formation

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