acylation

• what are the two possible reagents used in acylation?

  acyl chloride and acid anhydride
• acylation is the insertion of an acyl group into a compound
• what happens in acylation

  • the H of the O in the alcohol or water is replaced by an acyl compound
  • the N of the O of an amine or ammonia is replaced by an acyl group
  • the other product is an acid
  • with amines and ammonia the acid product reacts with a second molecule of amine or ammonia to form an ammonium salt of the acid
• overall mechanism of nucleophillic addition-elimination

  1. replaces a H on the O/N to give the main product
  2. if using an amine or ammonia , the acid by-product donates a H+ to another molecule of amine or ammonia
• what product is made by acylation from water

  carboxylic acid
• what product is made from acylation from alcohols

  ester
• what products are made from acylation of ammonia (NH3)

  amide
• what product is made by the acylation of amines(NH2)

  N-substituted amide
• both acyl chlorides and acid anhydrides have similar reactivity and are both more reactive than carboxylic acids and esters because they have good leaving groups
• the main difference between acyl chlorides and acid anhydrides are the by products, acyl chlorides produce HCL where's acid anhydrides produce RCOOH
• when an acyl chloride reacts with water a carboxylic acid and HCL gas is formed, this can be observed with a white steamy fume that is given off
• the reactions of nucleophiles with acyl chlorides and acid anhydrides are called nucleophillic addition-elimination reactions
• when an acyl chloride reacts with ammonia , a white smoke of NH4Cl is given off
• acyl chloride

  
• acyl anhydride