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Chemistry LibreTexts

20.13: Reaction of Organometallic Reagents with Carboxylic Acid Derivatives

  • Page ID
    28269
  • Addition of Grignard reagents convert esters to 3o alcohols.

    In effect the Grignard reagent adds twice.

    General Reaction

    File:/C:\Users\Gantor\AppData\Local\Temp\msohtmlclip1\01\clip_image002.png

    Example 1:
    2.jpg

    Mechanism

    1) Nucleophilic attack

    File:/C:\Users\Gantor\AppData\Local\Temp\msohtmlclip1\01\clip_image006.png

    2) Leaving group removal

    File:/C:\Users\Gantor\AppData\Local\Temp\msohtmlclip1\01\clip_image008.png

    3) Nucleophilic attack

    File:/C:\Users\Gantor\AppData\Local\Temp\msohtmlclip1\01\clip_image010.png

    4) Protonation

    File:/C:\Users\Gantor\AppData\Local\Temp\msohtmlclip1\01\clip_image012.png

    Organocuprate reagents convert acid chlorides to ketones

    General Reaction

    1.jpg

    Example 1:
    2.jpg

    Contributors

    Prof. Steven Farmer (Sonoma State University)

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