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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?

Answer: 4

💡 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: $NH_3 + 4C_2H_5Br \rightarrow (C_2H_5)_4N^+Br^- + 3HBr$.

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