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14.5 Acid Chloride Formation

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    25573
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    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

    1.jpg

    Example

    2.jpg

    Mechanism

    1) Nucleophilic attack on Thionyl Chloride

    3.jpg

    2) Removal of Cl leaving group

    4.jpg

    3) Nucleophilic attack on the carbonyl

    5.jpg

    4) Leaving group removal

    6.jpg

    5) Deprotonation

    7.jpg

    Contributors

    Prof. Steven Farmer (Sonoma State University)

    Further Reading

    MasterOrganic Chemistry

    Thionyl Chloride

    Khan Academy

    Acid Chloride Formation

    Chemtube3D

    Acid Chloride formation


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

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