In the Hofmann ammonolysis reaction, if of ammonia is reacted with a large excess of ethyl bromide, — Amines Chemistry Question
Question
In the Hofmann ammonolysis reaction, if $1\text{ mole}$ of ammonia is reacted with a large excess of ethyl bromide, what is the maximum number of moles of ethyl bromide that will be consumed by the nitrogen center to form the final major organic salt?
💡 Solution & Explanation
Ammonia acts as a nucleophile in successive $S_N2$ reactions. It reacts with the first mole to form a $1^\circ$ amine, a second mole to form a $2^\circ$ amine, a third to form a $3^\circ$ amine, and a fourth mole to form the final tetraethylammonium bromide (quaternary salt). Reaction: $NH_3 + 4C_2H_5Br \rightarrow (C_2H_5)_4N^+Br^- + 3HBr$.