JEE Main202315 Apr 2023Morning ShiftChemistryAminesActual
In the above conversion the correct sequence of reagents to be added is
Options
- Ai   KMnO 4 ,   ii   Br 2 / Fe ,   iii   Fe / H + ,   iv   Cl 2
- Bi   Br 2 / Fe ,   ii   Fe / H + ,   iii   KMnO 4 ,   iv   Cl 2
- Ci   Fe / H + ,   ii   HONO ,   iii   CuCl ,   iv   KMnO 4   v   B
- Di   Br 2 / Fe ,   ii   Fe / H + ,   iii   HONO ,   iv   CuCl   v  
Correct answer
D. i   Br 2 / Fe ,   ii   Fe / H + ,   iii   HONO ,   iv   CuCl   v  
Step-by-step solution
The required product can be obtained by the following method. In this method nitro toluene is subjected to bromination, bromo group is substituted at ortho position to the methyl as it is more activating group. Then nitro group is reduced to amine group with iron metal in acid. The amine group undergoes diazotisation with nitrous acid. The diazonium group is replaced with chloro group in the presence of cuprous chloride. Finally, methyl group is oxidised in the presence of potassium permanganate.