Carboxylic derivatives

• Carboxylic acid derivatives


  Obtained via the replacement of the OH with various substituents
• Carboxylic acid derivatives


  • Acid chloride
  • Anhydride
  • Ester
  • Amide
• Acid chloride


  Very reactive compounds with the general formula RCOCl
• Preparation of acid chlorides

  Reaction of carboxylic acid with thionyl chloride, SOCl2
• Ester


  Compounds with the general formula RCOOR'
• Preparation of esters


  1. Reaction of an alcohol with a carboxylic acid

  2. Reaction of an acid chloride with an alcohol
• Lactone


  Cyclic esters
• Preparation of lactones


  Dehydration of hydroxycarboxylic acid compound
• Amide


  Compounds with the general formula RCONHR'
• Preparation of amides


  1. Reaction of an acid chloride with an amine

  2. Reaction of a carboxylic acid with an amine, then heating
• Lactam


  Cyclic amides formed from amino acids
• Anhydride


  Compounds with the general formula RCOOCOR'
• Preparation of anhydrides


  Reaction of an acid chloride with a carboxylic acid in the presence of a pyridine base
• Nitrile


  Compounds with the general formula RCN
• Preparation of nitriles


  Reaction of ammonia, NH3 with carboxylic acid to yield an amide, then dehydration with POCl3
• Carboxylic acid derivatives


  • Undergo nucleophilic acyl substitution reactions
• Acid chloride reacts with an amine


  Yields an amide
• Esters are hydrolysed


  To carboxylic acid and alcohol
• Amides are reduced using metal hydrides


  Yields an amine
• Anhydrides are hydrolysed


  To carboxylic acid
• Nitriles are hydrolysed


  To a carboxylic acid, via a primary amide