ABSTRACT
Amines are molecules that contain a nitrogen atom. Primary and secondary amines (those with one or two carbon substituents connected to the nitrogen atom, respectively) have the ability to hydrogen bond with each other, but tertiary amines (with three carbon substituents and no hydrogen atoms connected to the nitrogen atom) cannot hydrogen bond with each other. Primary and secondary amines are only weakly electrophilic, and amine chemistry is dominated by the nucleophilicity of the amine nitrogen. While amines can undergo alkylation via SN2 reactions, the reactions are not clean. Alkylation of amines, therefore, is carried out through ersatz chemistry: azide substitution and reduction, Gabriel synthesis, and reductive amination. Amines can also be synthesized through the rearrangement of acyl azides in the Curtius rearrangement, which can also be used to synthesize ureas and carbamates. Finally, tetraalkyl ammonium ions can undergo elimination to form non-Zaitsev alkenes.
