ANHYDRIDE REACTION

[SKation]

Hi guys,

I had a question regarding the anhydride reaction. In general or specifically I was looking at the EK orgo book and saw that when 2 moles of amine react with an anhydride it still only forms one amide and one carboxylic acid. Why wouldn't 2 amides form?

Thanks!!!

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[DrknoSDN]

http://chemwiki.ucdavis.edu/Organic...d_Anhydrides_React_with_Amines_to_Form_Amides

Mechanism
1) Nucleophilic Attack by the Amine

2) Deprotonation by the amine

3) Leaving group removal

 

[syoung]

Also a leaving group that is a carboxylic conjugate base (COOR-) is a better leaving group than a NHR- group would be...
Look at the pkb of a COOR- and a NHR-