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In the above conversion the correct sequence of reagents to be added is

ChemistryAminesJEE MainJEE Main 2023 (15 Apr Shift 1)
Options:
  • A i KMnO4, ii Br2/Fe, iii Fe/H+, iv Cl2
  • B i Br2/Fe, ii Fe/H+, iii KMnO4, iv Cl2
  • C i Fe/H+, ii HONO, iii CuCl, iv KMnO4 v Br2
  • D i Br2/Fe, ii Fe/H+, iii HONO, iv CuCl v KMnO4
Solution:
2243 Upvotes Verified Answer
The correct answer is: i Br2/Fe, ii Fe/H+, iii HONO, iv CuCl v KMnO4

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.

 

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