Ch22: RX + NH3 - Chemistry

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Return to Contents Chapter 22: Amines Ch 22 contents
Alkylation of Ammonia alkylation of ammonia Reaction type: Nucleophilic Substitution

Summary

  • Ammonia reacts as a nucleophile with alkyl halides to give primary amines in a nucleophilic substitution reaction.
  • Yields are often poor as the product, a primary amine, RNH2, is itself a nucleophile and can react with more alkyl halide.
  • The result are mixtures containing primary amines, secondary amines, tertiary amines and quaternary ammonium salts.
  • This can be avoided if a large excess of ammonia is used.
repeated alkylation can be difficult to stop
  • As aryl halides do not undergo simple nucleophilic substitution, they cannot be prepared using this method.
Related reactions
  • Alkylation of Amines
  • Acylation of Amines
  • Williamson ether synthesis
  • Substitution reactions of Alkyl Halides
MECHANISM OF AMMONIA ALKYLATION
Step 1: The N in ammonia functions as the nucleophile and attacks the electrophilic C of the alkyl halide displacing the bromide and creating the new C-N bond. alkylation of ammonia : a simple SsubN/sub2 reaction
Step 2: An acid/base reaction. The base (excess ammonia) deprotonates the positive N (ammonium) center creating the alkylation product, the primary amine.
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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary

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