Acid Anhydride

STRUCTURE OF ACID ANHYDRIDE

• The word “anhydride” means without water
• Contains two molecules of an acid, with a loss of a molecule of water.
• Addition of water to anhydride regenerates two molecules of the
carboxylic acid
NOMECLATURE OF ACID ANHYDRIDE
• The word “acid” is changed to anhydride in both common name and
IUPAC name
• Example
• Ethanoic acid  ethanoic anhydride
• Propanoic acid  propanoic anhydride
• Anhydrides composed of two different acids are called mixed
anhydrides and are named by using the names of individual acids.

• Symmetrical anhydrides: change the word acid of the carboxylic acid

to the word anhydride

• Mixed anhydride: alphabetizing the names for both acids and

replacing the word acid with the word anhydride.
PREPARATION OF ACID ANHYDRIDES
• Acid chloride and carboxylic acid

• Acid chloride and carboxylate salt

• Heating carboxylic acid with ZnO

• Heating dicarboxylic acids

FROM ACYL CHLORIDES
1. Acyl Chloride reacts with carboxylate salts to form acid anhydrides.
• Can be used to prepare both symmetrical and unsymmetrical anhydrides
2. Acyl Chlorides also react with carboxylic acid to give acid anhydride.
HEATING CARBOXYLIC ACIDS WITH
ZnO
• Acid Anhydride can be prepared from heating simple carboxylic acids
with Zinc Oxide
HEATING DICARBOXYLIC ACIDS
• Certain cyclic anhydrides can be prepared by heating dicarboxylic acid
such as succine and phthalic anhydride.
REACTIVITY OF ACID ANHYDRIDE
• Comparing Acid Anhydride with Acyl Chlorides
• Ethanoic anhydride has a bulky ethanoate, CH3COO- group attached to the
carbonyl atom

• Ethanoyl Chloride has a simple Cl atom attached to the carbonyl atom.

• Therefore ethanoic anhydride is less reactive than ethanoyl Chloride.

REACTIONS OF ACID ANHYDRIDES
• Hydrolysis

• Alcoholysis

• Ammonolysis

• Friedel-Crafts acylation of benzene

HYDROLYSIS
• Acid anhydrides undergoes hydrolysis to produce carboxylic acids.
• Can be carried out in acid or base.
• Carboxylate salts are formed if hydrolysis is done in a basic solution.
ALCOHOLYSIS
• Acid anhydrides react with alcohol to produce esters and carboxylic
acids.

• Does not require a catalyst, but still require heating.

AMMONOLYSIS
• Amide can be prepared through ammonolysis of acid anhydrides with
ammonia, primary and secondary amines.
Examples: