Question

How will you convert the following? Chlorobenzene to Aniline.

Answer 1

Hint- Before giving the steps of conversion from chlorobenzene to Aniline we would like to discuss the process and its properties. Chlorobenzene is a colorless liquid with an aromatic smell. It is highly flammable. It reacts with ammonia to form aniline.

Complete step by step solution:

A mixture of chlorobenzene and ammonia is passed through a heated tube and then the tube is cooled and washed with water to remove the byproduct ammonium chloride and by fractional distillation the organic compound i.e. aniline is recovered. The best selectivity is obtained by using a high molar ratio of ammonia in comparison to chlorobenzene.
Reaction
The chlorobenzene is reacted with alcoholic KOH at 400 degree Celsius to form phenol which passed through zinc dust to form benzene
$Ph - Cl\xrightarrow[{{{400}^0}C}]{{alc.KOH}}Ph - OH\xrightarrow{{Zndust}}{C_6}{H_6}$
The benzene is reacted with the sulphuric acid and nitric acid to form nitrobenzene which is further treated with HCl in the presence of catalyst tin and the product obtained is aniline.
${C_6}{H_6}\xrightarrow{{HN{O_3} + {H_2}S{O_4}}}Ph - N{O_2}\xrightarrow{{Sn + HCl}}Ph - N{H_2}$

Additional information-
Anilines are organic compounds that are also called aminobenzene or phenylamine in the group class in organic chemical processes. Such compounds are known to be toxic in nature and are also one of the aromatic amines groups. Their use is considered to have all the features of an aromatic compound and to have a number of industrial uses.

Note-Aniline is a primary amine. Aniline is used to make dyes, drugs, explosives, plastics etc. The preparation method of aniline includes hydrogenation of nitrobenzene or by the action of ammonia or chlorobenzene. Aniline is reacted with alkyl halide to prepare secondary aromatic amine and more compounds like this.