further chem
nitrile:

  • under acid, base
  • proceeds to carboxylic acid (or carboxylate ion) + ammonia or ammonium salt

ester:

  • under acid, base
  • proceeds to carboxylic acid (or carboxylate ion) + alcohol

amide:

  • under acid, base, or enzyme:
  • proceeds to carboxylic acid + ammonia