Dehydration of amides to give nitriles

by James

Description: Primary amides can be converted to nitriles with a dehydrating reagent such as P2O5 .
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{ 2 comments… read them below or add one }

Chan May 23, 2013 at 9:38 am

Hi James,
My question may sound silly,but i seriously have no idea.Why ‘P’ in P2O5 is attracted by the pi bonds and not the lone pairs of Amine group?

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james May 23, 2013 at 4:37 pm

Lone pair of amide is strongly donating into carbonyl carbon – there is pseudo double bond character between carbon and nitrogen. Oxygen is very nucleophilic.

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