Chapter 22: Amines

Summary

• Amines can react as a nucleophiles with alkyl halides via substitution reactions (S_N2)
• Yields are often poor as the product amines, are still nucleophilic and can react with more halide.
• The result is often a mixture of amines in various states of alkylation.

• Alkylation of Ammonia
• Acylation of Amines
• Williamson Ether synthesis
• Substitution reactions of Alkyl Halides

MECHANISM OF AMINE ALKYLATION
Step 1: The amine N functions as the nucleophile and attacks the electrophilic C of the alkyl halide displacing the bromide and creating the new C-N bond.
Step 2: An acid/base reaction. The base (excess amine) deprotonates the positive N (ammonium) center creating the alkylation product, here a secondary amine.

© Dr. Ian Hunt, Department of Chemistry