Return to Contents  Chapter 20: Carboxylic Acid Derivatives. NucleophilicAcyl Substitution  Ch 20 contents

Hydrolysis of Nitriles

hydrolysis of nitriles
Reaction type:  Nucleophilic Addition then NucleophilicAcyl Substitution

Summary

Related Reactions
MECHANISM OF THE ACID CATALYSED HYDROLYSIS OF NITRILES
Step 1:
An acid/base reaction. Since we only have a weak nucleophile so activate the nitrile, protonation makes it more electrophilic.
hydrolysis of a nitrile with acid catalysis
Step 2:
The water O functions as the nucleophile attacking the electrophilic C in the C≡N, with the electrons moving towards the positive center. 
Step 3:
An acid/base reaction. Deprotonate the oxygen that came from the watermolecule. The remaining task is a tautomerisation at N and O centers.
Step 4:
An acid/base reaction. Protonate the N gives us the -NH2 we need.... 
Step 5:
Use the electrons of an adjacent O to neutralise the positive at the N and form the π bond in the C=O
Step 6:
An acid/base reaction. Deprotonation of the oxonium ion reveals the carbonyl in the amide intermediate....halfway to the acid..... 
What about the rest

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary