3.3.9.2 acylation

• acid anhydrides


  formed when water is removed from 2 carboxylic acids

  
• acyl chlorides 


  react violently due to the very polar -COCl group

  
• amides 


  reacts to form N-substituted amides

  
• nucleophilic addition-elimination reactions


  addition of a nucleophile leads to the elimination of a product under aqueous conditions
• nucleophilic addition-elimination mechanism

  
• acyl chlorides + water = carboxylic acid
• acyl chlorides + alcohol = ester
• acyl chloride + ammonia = amide
• acyl chloride + amines = N-substituted amide
• aspirim


  ester produced from salicylic acid and ethnic anhydride

  
• ethanoyl chloride

  used to produce aspirin
• why is ethanoyl chloride not used in industry?

  expensive and produces harmful HCl fumes
• ethnic anhydride


  much safer for industrial use