CIE A Level Chemistry (9701) exams from 2022

Revision Notes

7.6.1 Production of Amines

Production of Primary & Secondary Amines

  • Primary amines are organic compounds that have an -NH2 functional group attached to an alkyl or aryl group
  • Secondary amines have two alkyl or aryl groups attached to an -NH group

 

Nitrogen Compounds - Primary and Secondary Amines, downloadable AS & A Level Chemistry revision notes

Primary and secondary amines

  • Primary and secondary amines can be prepared from different reactions including:
    • The reaction of halogenoalkanes with ammonia
    • The reaction of halogenoalkanes with primary amines
    • The reduction of amides
    • The reduction of nitriles

Reaction of halogenoalkanes with ammonia

  • This is a nucleophilic substitution reaction in which the nitrogen lone pair in ammonia acts as a nucleophile and replaces the halogen in the halogenoalkane
  • When a halogenoalkane is reacted with excess, hot ethanolic ammonia under pressure a primary amine is formed

 

Nitrogen Compounds - Primary Amine Formation, downloadable AS & A Level Chemistry revision notes

Formation of primary amine

Reaction of halogenoalkanes with primary amine

  • This is also a nucleophilic substitution reaction in which the nitrogen in the primary amine acts as a nucleophile and replaces the halogen in the halogenoalkane
  • When a halogenoalkane is reacted with a primary amine in ethanol and heated in a sealed tube, under pressure a secondary amine is formed

 

Nitrogen Compounds - Secondary Amine Formation, downloadable AS & A Level Chemistry revision notes

Formation of secondary amine

Reduction of amides

  • Amines can also be formed from the reduction of amides by LiAlH4 in dry ether
  • Whether a primary or secondary amine is formed depends on the nature of the amide

 

Amides can be reduced by LiAlH4 to form amines

Reduction of nitriles

  • Nitriles contain a -CN functional group which can be reduced to an -NH2 group
  • The nitrile vapour and hydrogen gas are passed over a nickel catalyst or LiAlH4 in dry ether can be used to form a primary amine

 

Nitrogen Compounds - Reduction of Nitriles, downloadable AS & A Level Chemistry revision notes

Nitriles can be reduced with LiAlH4 or H2 and Ni catalyst

Author: Francesca

Fran has taught A level Chemistry in the UK for over 10 years. As head of science, she used her passion for education to drive improvement for staff and students, supporting them to achieve their full potential. Fran has also co-written science textbooks and worked as an examiner for UK exam boards.
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