11.1.6 Electrophilic Addition to Nitriles
- Page ID
- 22811
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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
Example
Mechanism
1) Protonation
2) Nucleophilic attack by water
3) Proton Transfer
4) Resonance
5) Deprotonation
Contributors
Prof. Steven Farmer (Sonoma State University)