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:
- Amixture of - and -bromotoluenes
- Bmixture of - and -dibromobenzenes
- Cmixture of - and -bromoanilines
- Dmixture of - and -bromotoluenes
Solution & Step-by-step Explanation

1. Nitration of Toluene: group is directing. Nitration yields -nitrotoluene and -nitrotoluene.2. Reduction with Sn/HCl: group is reduced to . This gives -toluidine and -toluidine.3. Diazotization (NaNO /HCl): is converted to .4. Sandmeyer Reaction (CuBr): is replaced by .Final products are -bromotoluene and -bromotoluene.