Aromatic Compounds Containing Nitrogen - Result Question 54

56. How would you convert aniline into chlorobenzene?

(1985, 1M)

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Solution:

$\mathrm{C}_6 \mathrm{H}_5-\mathrm{NH}_2 \xrightarrow[0^{\circ} \mathrm{C}]{\mathrm{NaNO}_2 / \mathrm{HCl}} \mathrm{C}_6 \mathrm{H}_5 \mathrm{~N}_2^{+} \mathrm{Cl}^{-} \xrightarrow[\text { Heat }]{\mathrm{CuCl}} \mathrm{C}_6 \mathrm{H}_5-\mathrm{Cl}$