|Chapter 20: Carboxylic Acid Derivatives. NucleophilicAcyl Substitution|
Hydrolysis of Nitriles
MECHANISM OF THE ACID CATALYSED HYDROLYSIS OF NITRILES
An acid/base reaction. Since we only have a weak nucleophile so activate the nitrile, protonation makes it more electrophilic.
The water O functions as the nucleophile attacking the electrophilic C in the C≡N, with the electrons moving towards the positive center.
An acid/base reaction. Deprotonate the oxygen that came from the watermolecule. The remaining task is a tautomerisation at N and O centers.
An acid/base reaction. Protonate the N gives us the -NH2 we need....
Use the electrons of an adjacent O to neutralise the positive at the N and form the π bond in the C=O.
An acid/base reaction. Deprotonation of the oxonium ion reveals the carbonyl in the amide intermediate....halfway to the acid.....
What about the rest ?
|© Dr. Ian Hunt, Department of Chemistry|