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Review: Synthesis of Carboxylic Acid Derivatives

  • Page ID
    26164
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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

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    Example

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    Mechanism

    1) Nucleophilic attack on Thionyl Chloride

    3.jpg

    2) Removal of Cl leaving group

    4.jpg

    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)


    Review: Synthesis of Carboxylic Acid Derivatives is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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