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Master Organic Chemistry Reaction Guide

Dehydration of amides to give nitriles

Description: Primary amides can be converted to nitriles with a dehydrating reagent such as P2O5 .

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Real-Life Examples:

Org. Synth. 1930, 10, 66

DOI Link: 10.15227/orgsyn.010.0066

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Org. Synth. 1945, 25, 61

DOI Link: 10.15227/orgsyn.025.0061

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Org. Synth. 1945, 25, 63

DOI Link: 10.15227/orgsyn.025.0063

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Org. Synth. 1950, 30, 22

DOI Link: 10.15227/orgsyn.030.0022

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Org. Synth. 1950, 30, 46

DOI Link: 10.15227/orgsyn.030.0046

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Org. Synth. 1953, 33, 52

DOI Link: 10.15227/orgsyn.033.0052

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Comments

Comment section

6 thoughts on “Dehydration of amides to give nitriles

  1. 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?

    1. 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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