Question

Toluene is nitrated, and the resulting product is reduced with tin and hydrochloric acid. The product obtained is diazotized and heated with cuprous bromide. The reaction mixture formed contains :
(A) Mixture of o - and p - bromoanilines
(B) Mixture of o - and m - bromotoulenes
(C) Mixture of o - and p - bromotoulenes
(D) Mixture of o - and p - dibromobenzenes

Answer 1

Hint: Toluene is a transparent, colourless liquid that, when heated to room temperature, turns into a vapour. Toluene is a naturally occurring component of crude oil and is used in the production of paints, lacquers, explosives (TNT), and glues, in addition to oil refining. Toluene exposure can lead to a variety of symptoms, including irritation of the eyes and nose, exhaustion, headache, dilated pupils, tears, anxiety, muscle fatigue, sleeplessness, and nerve damage.

Complete Step by Step Answer:
In the first step, toluene is nitrated with nitric acid ($HN{{O}_{3}}$), it forms o - and p - nitrotoulenes. The nitrotoulenes on reduction with tin and hydrochloric acid ($HCl$) forms o- and p- toulidine. When these toulidines is diazotized and heated with cuprous bromide, the product formed is a mixture of o-and p-bromotoulenes.

Correct Option: (C) Mixture of o - and p - bromotoulenes.

Note: The methyl group present in toluene is an electron-donating group. The methyl group activates the benzene ring. The electron donating groups are o - and p - directing. On the other hand, if an electron releasing group is attached to a ring, it deactivates the ring.