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Chemistry LibreTexts

20.12 Reaction of Organometallic Reagents with Carboxylic Acid Derivatives

  • Page ID
    28389
  • Addition of Grignard reagents -- convert esters to 3o alcohols.

    When reacting with esters, the Grignard reagent adds twice. The first addition forms a ketone, but Grignard reagents are strong enough nucleophiles to add to ketones as well. Therefore, the reaction continues to the tertiary alcohol.

    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)

    • Layne A. Morsch - University of Illinois Springfield
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