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

Nucleophilic Acyl Substitution : Reactive Systems

Step 1:
The nucleophile adds to the electrophilic C in the polar carbonyl group, electrons from the C=O move to the electronegative O creating the tetrahedral intermediate.
nucleophilic acyl substitution for reactive systems
Step 2:
The intermediate collapses, reforming the strong C=O bond results in the loss of the leaving group, leading to the new carbonyl containing system.

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