Chapter 20: Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution

Summary

The carboxylic acid derivatives are a family of closely related functional groups:

• each contain a C=O group with a heteroatom attached

(note : this is what distinguishes them from aldehydes and ketones)
• they can all be prepared from the "parent" carboxylic acid (review Ch19)
• on hydrolysis (reaction with H₂O) they all convert back to the parent carboxylic acid
• they share a common reactivity pathway with nucleophiles: nucleophilic acyl substitution.

The most important things to know about carboxylic acid derivatives are:

• how to prepare the derivatives from the carboxylic acid itself (chapter 19)
• the relative reactivity of the carboxylic acid derivatives.
• that hydrolysis of derivatives gets you back to the carboxylic acid.
• the mechanism of nucleophilic acyl substitution.

• Nomenclature
• Structure
• Reactivity

Nucleophilic Acyl Substitution

• Overview
• Summary of Reactions that Interconvert Carboxylic Acids Derivatives

• Reactions of Acyl Halides, Friedel-Crafts Acylation (review)
• Reactions of Acid Anhydrides,
• Reactions of Esters, Hydrolysis, Reduction, and with Grignard reagents
• Reactions of Amides, Hydrolysis and Reduction
• Reactions of Nitriles, Hydrolysis, Reduction, and with Grignard reagents

Problems

• Sample Problems

© Dr. Ian Hunt, Department of Chemistry