Chapter 19 * Alkylation of Amines by Alkyl Halides Even if just one equivalent of the halide is added, some amine molecules will react once, some will react twice, and some will react three times (to give the tetraalkylammonium salt). Chapter 19 * Examples of Useful Alkylations Exhaustive alkylation to form the tetraalkylammonium salt. Reaction with large excess of NH3 to form the primary amine. C H 3 C H 2 C H C H 2 C H 2 C H 3 N ( C H 3 ) 3 C H 3 C H 2 C H C H 2 C H 2 C H 3 N H 2 3 C H 3 I N a H C O 3 + _ I C H 3 C H 2 C H 2 B r N H 3 ( x s ) C H 3 C H 2 C H 2 N H 2 + N H 4 B r Chapter 19 Chapter 19 * Acylation of Amines Primary and secondary amines react with acid halides to form amides. This reaction is a nucleophilic acyl substitution. Chapter 19 *