JEE Main 2023 · 8 April · evening · Single correct · +4 / −1
The product (P) formed from the following multistep reaction is:
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (a)
Solution
Chemistry ma’am · 4 steps
The nitro group only steers the bromine; then H₃PO₂ wipes the nitrogen off the ring.
- Where bromine goes. In p-nitrotoluene, CH₃ is an ortho/para director and NO₂ is a meta director. The para position of CH₃ is already taken, so both groups point to the same carbon: ortho to CH₃ and meta to NO₂. This gives 2-bromo-4-nitrotoluene.
- Nitro to amine. H₂/Pd reduces -NO₂ to -NH₂, giving 2-bromo-4-methylaniline. Then NaNO₂ and HCl at 0 °C turn -NH₂ into the diazonium group -N₂⁺Cl⁻.
Ar-N₂⁺Cl⁻ + H₃PO₂ + H₂O → Ar-H + N₂ + H₃PO₃ + HCl
- Remove the nitrogen. Hypophosphorous acid replaces -N₂⁺ with H, not with OH. So the ring carbon that held the nitrogen ends up bare, and only CH₃ and Br remain, side by side.
- So. P is 2-bromotoluene (o-bromotoluene), which is option (a).
The idea to keep. Use NO₂ to NH₂, then diazotisation and H₃PO₂, when a group is needed only to steer substitution. It sets the position, then leaves as N₂ with H in its place.
Answer from the NTA final answer key. Solution by PrepWiser.