Organic Chemistry by Brown, Iverson, Anslyn, Foote | Mayya's Study Guide | Chapter 18

Chapter 18: Functional Derivatives of Carboxylic Acids

Table of Contents:

1. Structure

2. Acidity of Amides, Imides, and Sulfonamides

3. Characteristic Reactions

4. Reaction with Water: Hydrolysis

5. Reaction with Alcohols

6. Reactions with Ammonia and Amines

7. Reaction of Acid Chlorides with Salts of Carboxylic Acids

8. Reactions with Organometallic Compounds

9. Reduction

Structure

carboxylic acid derivatives

Acidity of Amides, Imides, and Sulfonamides

Characteristic Reactions

Under basic conditions, the nucleophile attacks the carbonyl carbon pushing electrons up to the oxygen. Under acidic conditions, oxygen first gets protonated which is followed by the nucleophile attack.

reactivity of carboxylic acid derivatives

Reactions With Water: Hydrolysis

Acid Chloride or Anhydride with H2O = Carboxylic Acid

Reaction of acid chloride or anhydride with water

Mechanism

mechanism for conversion of acid chloride into carboxylic acid

Hydrolysis of Esters

Esters can be converted into carboxylic acids under acidic or basic conditions.

hydrolysis of esters

Mechanisms

Mechanism Of Ester Hydrolysis In Acid

Mechanism Of Ester Hydrolysis In Base

Hydrolysis of Amides

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