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Toluene is first nitrated. The nitro compound obtained is then reduced using tin and hydrochloric acid. The amine formed is diazotized and the diazonium salt is subsequently heated with cuprous bromide. The final reaction mixture contains

1. a mixture of ortho- and para-bromotoluenes
2. a mixture of ortho- and para-dibromobenzenes
3. a mixture of ortho- and para-bromoanilines
4. a mixture of ortho- and meta-bromotoluenes

Correct answer: a mixture of ortho- and para-bromotoluenes

Solution

The nitration of toluene introduces a nitro group, which directs further electrophilic substitution reactions to the ortho and para positions. The reduction of the nitro group to an amine followed by diazotization and reaction with cuprous bromide leads to bromination at these same positions, resulting in a mixture of ortho- and para-bromotoluenes.

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