NUCLEOPHILES

• WHEN DO AMINES/ AMMONIA REACT AS NUCLEOPHILES?

  with halogenoalkanes in nucleophilic substitution
• REACTION OF AMMONIA WITH HALOGENOALKANES?

  NH3 + RX -> [RNH3]+X-

  [RNH3]+X- + NH3 -> RNH2 + [NH4]+X-
• REACTION OF PRIMARY AMINES WITH HALOGENOALKANES?

  RNH2 + RX -> [R2NH2]+X-

  [R2NH2]+X- + NH3 -> R2NH + [NH4]+X-
• REACTION OF SECONDARY AMINES WITH HALOGENOALKANES?

  R2NH + RX -> [R3NH]+X-

  [R3NH]+X- + NH3 -> R3N + [NH4]+X-
• REACTION OF TERTIARY AMINES WITH HALOGENOALKANES?

  R3N + RX -> [R4N]+X- (quaternary ammonium salt)
• WHAT IS PRODUCED WHEN AMMONIA REACTS WITH HALOGENOALKANES?

  mixture of primary/ secondary/ tertiary amines and quaternary ammonium salts (must be separated via fractional distillation)