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Chemistry LibreTexts

Conversion of nitriles to amides

Nitriles can be converted to amides. This reaction can be acid or base catalyzed.  In the case of acid catalysis the nitrile becomes protonated. Protonation increases the electrophilicity of the nitrile so that it will accept water, a poor nucleophile.

General reaction

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Example

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Mechanism

1) Protonation

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2)  Nucleophilic attack by water

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3) Proton Transfer

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4) Resonance

 

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5) Deprotonation

 

 

Contributors

Prof. Steven Farmer (Sonoma State University)