Key Terms

  • alkylamine
  • amine
  • arylamine
  • azo compound (R–N=N–R′)
  • Curtius rearrangement
  • Gabriel amine synthesis
  • heterocyclic amine
  • Hofmann elimination reaction
  • Hofmann rearrangement
  • imide (O=C–N–C=O)
  • primary amine (RNH2)
  • quaternary ammonium salt
  • reductive amination
  • Sandmeyer reaction
  • secondary amine (R2NH)
  • tertiary amine (R3N)
Summary of Reactions 12
  • Synthesis of amines (Section 12.4)
  • Reduction of nitriles

An alkyl halide reacts with sodium cyanide to form cyano nitrile. This reacts with lithium aluminum hydride in ether, then water to form an amine.

  • Reduction of amides

An amide reacts with lithium aluminum hydride in ether, then water to form an amine.

  • Reduction of nitrobenzenes

Nitrobenzene reacts with hydrogen, platinum, or iron, hydronium or tin (II) chloride, hydronium ion to form aniline.

  • SN2 Alkylation of alkyl halides

The primary, secondary, and tertiary amine and quaternary ammonium salt are formed from ammonia, primary, secondary, and tertiary amine, respectively.

  • Reduction of azides

An alkyl halide reacts with sodium azide and ethanol to form a compound that further reacts with lithium aluminum hydride in ether, then water to form an amine.

  • Reductive amination of aldehydes/ketones

A carbonyl compound reacts with ammonia and sodium borohydride to form a secondary amine.

Reactions of amines

  • Alkylation with alkyl halides
  • Acylation of acyl chlorides

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Fundamentals of Organic Chemistry Copyright © by Kirsten Kramer and Cassandra Lilly is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

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