Ammonolysis of Alkyl Halides (Hofmann's Method)

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$$\text{R--X} \xrightarrow{\text{NH}_3 \text{ (alc.)}} \text{R--NH}_2 \xrightarrow{\text{R--X}} \text{R}_2\text{NH} \xrightarrow{\text{R--X}} \text{R}_3\text{N} \xrightarrow{\text{R--X}} [\text{R}_4\text{N}]^+\text{X}^-$$

(Yields a mixture of $1^\circ, 2^\circ, 3^\circ$ amines and $4^\circ$ quaternary ammonium salts; excess $\text{NH}_3$ yields $1^\circ$ amine as major product)

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