Question

Identify the major product from the following reaction sequence:

• A.

  

• B. 4-Bromo-2-methylbenzene
  

  

• C.

  

• D.

  

Hint:

For Sandmeyer reactions, the halogen replaces the diazonium (\ch{N2^+}) group.
The substituent's position stays fixed unless rearrangement occurs.

Answer 1

The Correct Option is D

The reaction involves: 1. Nitration of toluene at elevated temperatures introduces a nitro group at para and ortho positions. 2. Reduction of nitro group to \ch{NH2} (aniline derivative). 3. Bromination via Sandmeyer reaction using \ch{NaNO2}, \ch{HCl}, and \ch{CuBr} leads to substitution of \ch{NH2} with Br at original position. Final product: 2-bromo-4-methylbenzene.