amines

• Amines


  Compounds with a nitrogen atom attached to one or more alkyl or aryl groups
• Naming amines


  • End in -amine
  • Two ways of using this suffix: common version where the name stem ends in -yl, IUPAC version where the name stem ends in -an-1-
• Naming amines with another priority functional group

  Use the prefix amino-
• Naming secondary amines


  Each alkyl chain is named and the smaller alkyl group is preceded by an -N
• Naming tertiary amines


  Each alkyl side group is given an N
• Primary aliphatic amines


  • Act as Bronsted-Lowry bases because the lone pair of electrons on the nitrogen is readily available for forming a dative covalent bond with a H+ and so accepting a proton
  • Stronger bases than ammonia as the alkyl groups are electron releasing and push electrons towards the nitrogen atom
• Primary aromatic amines


  Do not form basic solutions because the lone pair of electrons on the nitrogen delocalise with the ring of electrons in the benzene ring
• Reactions of amines with acids

  1. Form ammonium salts

  2. Addition of NaOH to an ammonium salt will convert it back to the amine
• Nucleophilic substitution reaction between haloalkanes and ammonia


  1. Forms primary amines

  2. Excess ammonia dissolved in ethanol is the reagent

  3. Mechanism: nucleophilic attack on haloalkane to form intermediate, then second ammonia removes proton to form amine
• Reacting primary amines with haloalkanes


  Forms secondary amines
• Reacting secondary amines with haloalkanes


  Forms tertiary amines
• Reducing nitroarenes to aromatic amines

  1. Reagent: Sn and concentrated HCl

  2. Conditions: Heating

  3. Mechanism: reduction
• The nitro group on an arene can be reduced to an amine group