Amines

Amines

Properties of Amines

  • Amines are a class of organic compounds that contain nitrogen.
  • They can be viewed as derivatives of ammonia where one or more hydrogen atoms are replaced by an alkyl or aryl group.
  • Their structure can be primary, secondary or tertiary, depending on the number of alkyl/aryl groups attached to the nitrogen.
  • They are generally classified as weak bases due to the lone pair of electrons on the nitrogen atom that can accept a proton (H+).
  • Amines with lower molecular weights are often gaseous at room temperature and have fishy odours.

Forming Amines

  • A primary amine can be made by the nucleophilic substitution reaction between haloalkanes and excess ammonia.
  • Secondary and tertiary amines can be made in a similar way, but the reaction rate is slower and requires a larger excess of ammonia.
  • The reaction of alcohol with ammonia in the presence of an acid catalyst can form an amine.
  • Amide reduction using LiAlH4 or by catalytic hydrogenation can produce amines.

Reactions of Amines

  • Amines react with acids to form ammonium salts.
  • When amines react with halogenoalkanes, they undergo N-substitution to form secondary, tertiary amines, and quaternary ammonium salts.
  • The reaction of amines with nitrous acid (HNO2) can form different products depending on whether the amine is primary, secondary, or tertiary.

Developing Understanding

  • Being able to predict the physical and chemical properties of various amines is an important skill.
  • Draw mechanisms for reactions involving amines and be able to predict products for given starting materials.
  • Understanding the ways in which amines can be synthesised will also extend your understanding of organic synthesis more broadly.
  • Familiarity with these properties and reactions is key for predicting the behaviour of amines in organic chemistry and biochemistry.