text: Acid anhydrides are a source of reactive acyl groups, and their reactions and uses resemble those of acyl halides. In reactions with protic substrates, the reactions afford equal amounts of the acylated product and the carboxylic acid:
  :RC(O)OC(O)R + HY → RC(O)Y + RCOH
  for HY = HOR (alcohols), HNR' (ammonia, primary, secondary amines), aromatic ring (see Friedel-Crafts acylation).
  Acid anhydrides tend to be less electrophilic than acyl chlorides, and only one acyl group is transferred per molecule of acid anhydride, which leads to a lower atom efficiency. The low cost, however, of acetic anhydride makes it a common choice for acetylation reactions.