Alkylation of Ammonia to Make Amines

To make only primary amines, chemists use specific reaction conditions such as excess ammonia. Ammonia is the most common substrate because it is cheap and readily available. Tertiary alkyl halides are not the best choice for alkylation because they are too hindered. Secondary alkyl halides can react, but they are also less ...

Ammonia and alkyl halides react through alkylation of nitrogen via an S_N2 mechanism to give monoalkylammonium salts, which on subsequent deprotonation give primary alkylamines.  

Alkylation makes the nitrogen center more nucleophilic, and successive alkylations repeat until all N–H protons are substituted with alkyl groups. Thi...