Attacking Acid Anhydrides with Hard & Soft Nucleophiles

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Practice Resources:

Guided Worksheet(s) + Solutions:
Worksheet Solutions Walkthrough(s):
-   Practicing Rxns of Carboxylic Acid Derivatives
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Description

https://joechem.io/videos/76 for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link). In this video, we look at addition-elimination reactions with acid anhydride functional groups and how these reactions differ (in mechanism and product) when a hard vs soft nucleophile is used in the addition-elimination pathway.

Tags:  carbonyl acid halide soft nucleophile addition-elimination mechanism tetrahedral intermediate

Comments:


  • Hayley Denwood • 5 years ago
    Hi Joe! As you were breaking down the tetrahedral intermediate, you formed the carboxylic acid's conjugate base. After removing the proton from the ester, you formed a carboxylic acid. Could you then take that carboxylic acid and have the EtOH in solution react with it to form another ester? Thank you!

    REPLY
    • Joe Del Nano • 5 years ago
      That could absolutely happen--yes! Obviously the intent of the reaction (when I picked this example) was to show the attack of a soft nucleophile on a acid anhydride, but that could absolutely happen and be a continuation of the reaction : )

      REPLY
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