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Question

Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is diazotized and heated with cuprous bromide. The reaction mixture formed contains :

A
Mixture of o- and p- bromoanilines
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B
Mixture of o- and m- bromotoluenes
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C
Mixture of o- and p- bromotoluenes
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D
Mixture of o- and p- dibromobenzenes
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Solution

The correct option is C Mixture of o- and p- bromotoluenes
Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is diazotized and then, heated with cuprous bromide. The reaction mixture so formed contains mixture of o- and p- bromotoluenes.
The reactions are shown in the figure.

379187_41038_ans.gif

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