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Amines: Reactivity, Reactions and Mechanisms

Amines are organic compounds that contain a nitrogen atom with a lone pair of electrons. This lone pair of electrons makes amines nucleophi...


Amines are organic compounds that contain a nitrogen atom with a lone pair of electrons. This lone pair of electrons makes amines nucleophilic, meaning that they are attracted to electron-deficient atoms, and also basic, meaning that they can accept a proton from an acid. Amines can react in a variety of ways, including:
  • Acylation: Amines can react with acid chlorides, anhydrides, or esters to form amides.
  • Alkylation: Amines can react with alkyl halides to form alkylated amines.
  • Amination: Amines can react with carbonyl compounds to form imines or amides.
  • Diazotization: Amines can react with nitrous acid to form diazonium salts.
  • Oxidation: Amines can be oxidized to form imines, nitriles, or amides.
  • Reduction: Amines can be reduced to form alkanes or alkenes.

The specific reaction that an amine undergoes depends on the structure of the amine and the reaction conditions. The reaction conditions also play a role in determining the outcome of the reaction. For example, amines can be alkylated under acidic conditions or basic conditions.


Topics

  • Reactivity of amines
  • Amines as a base
  • Implication of pKa in the direction of the reaction
  • Solubility of amines
  • Application of protonated amines
  • Factors affecting the basicity of amines
  • Amines as a nucleophile
  • Amines as a leaving group
  • Reactions and mechanisms of amines