Carboxylic Acids and Derivatives

• Acyl Chlorides and Acid Anhydrides
• Acyl Chlorides have the functional group -COCl
• Acid Anhydrides have the function group -RCOOCOR
• Acid Chloride + water -> carboxylic acid +HCl
• Acid Chloride + alcohol -> ester + HCl
• Acid Chloride + 2 NH3 -> amide + HCl
• Acid Chloride + 2 primary amines -> N-substituted amine + HCl
• HCl is toxic
• Acid Anhydride + water -> carboxylic acid
• Acid Anhydride + NH3 -> amide + carboxylic acid
• Acid Anhydride + alcohol -> ester + carboxylic acid
• Acid Anhydride + primary amine -> N-substituted amine + carboxylic acid
• Acyl Chloride is:

  • violently reactive and difficult to control
  • produces corrosive HCl gas
  • more expensive than Acid anhydride
• Both react with:

  • water
  • alcohol
  • ammonia
  • primary amines