3.3.11.1 preparation of amines

• how are amines produced?

  when one or more of the hydrogen atoms in ammonia is replaced with an organic group
• they can be primary, secondary or tertiary amines depending on how many hydrogen atoms are replaced
• types of amines

  
• nucleophilic substitution of amines

  
• nucleophilic substitution

  • amines produced from reaction of a halogenoalkane with ammonia in a sealed tube
  • 1 mole of halogenoalkane reacts with 2 moles of ammonia producing a primary amine and an ammonium salt
• this substitution reaction can continue until all the hydrogen atoms have been replaced with organic groups
• an additional substation can occur, producing a quaternary ammonium salt
• further substitutions of amines

  
• what does the multiple number of possible substitutions mean?

  a mixture of products are produced
• what is the efficiency of the reaction?

  low
• why do the reaction conditions have to be changed?


  so that only a single substitution occurs
• what can ammonia be added in excess to achieve?


  only the primary amine
• what can the mixture of products be separated using?

  fractional distillation
• what can reducing nitriles via hydrogenation produce?

  amines
• reagent and conditions in reduction of nitriles

  LiAlH4 - reducing agent, acidic conditions or a combo of hydrogen and nickel (catalytic hydrogenation)
• reduction of nitriles to amines

  
• how can aromatic amines be produced?

  reduction of nitrobenzene
• reduction of nitrobenzene conditions and reagents

  conc. HCl and tin catalyst
• reduction of nitrobenzene

  
• what makes amines good conditioners?

  the negative and positive end of the complex molecules are attracted to different substances, preventing static from building up on surfaces
• what are canonic surfactants useful in?


  industry