Thursday, May 19, 2011

MECHANISM OF THE ACID catalyzed 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 CยบN, with the electrons moving towards the positive center.

Step 3:
An acid/base reaction. Deprotonate the oxygen that came from the water molecule. The remaining task is a tautomerization 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 p 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.....

2 comments:

  1. Creatinine Amidohydrolase catalyzes the hydrolytic reaction converting creatinine to creatine. The enzyme is purified from a microorganism. The molecular size of the enzyme is approximately 175,000. Creatinine amidohydrolase

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