Acid Anhydrides and Their Reactions
Start with the big picture
Anhydrides may be symmetrical, mixed, or cyclic; common preparation routes include combining an acyl chloride with a carboxylate, dehydrating carboxylic acids, and closing a dicarboxylic acid into a ring. Their carbonyls are electrophilic, and carboxylate is the leaving group. In the central substitution mechanism, nucleophilic attack forms a tetrahedral intermediate, which then collapses to restore the carbonyl. Reaction partners determine the outcome: hydrolysis gives carboxylic acids, alcoholysis gives an ester and a carboxylic acid, and aminolysis gives an amide. Organometallic reagents, hydride reagents, and Friedel–Crafts conditions provide additional pathways. The lesson also addresses identification, naming, applications, and safe handling.
What you'll learn
- Distinguish symmetrical, mixed, and cyclic acid anhydrides.
- Identify common methods for preparing acid anhydrides.
- Describe the tetrahedral-intermediate pathway of nucleophilic acyl substitution.
- Relate hydrolysis, alcoholysis, and aminolysis to their products.
- Recognize key spectroscopic features and handling hazards.
Continue your study
Work through the complete notes and reinforce the topic with the study tools available in the full lesson.