JEE Main 2023 (8 Apr, Shift 2) Chemistry Q76: Amines

Question

The product (P) formed from the following multistep reaction is:
[reaction: 4-nitrotoluene (benzene ring with $\mathrm{NO_2}$ and $\mathrm{CH_3}$ para to each other) $\xrightarrow{	ext{(i) } Br_2;\ 	ext{(ii) } H_2/Pd;\ 	ext{(iii) } NaNO_2,\ HCl,\ 0^\circ C;\ 	ext{(iv) } H_3PO_2}$ (P) Product]

Accepted Answer

Option 1: [structure: 2-bromotoluene, Br on the carbon adjacent to the $\mathrm{CH_3}$-bearing carbon]

Answer

[structure: 2-bromotoluene, Br on the carbon adjacent to the $\mathrm{CH_3}$-bearing carbon]

Answer

[structure: 3-bromotoluene, Br meta to $\mathrm{CH_3}$]

Answer

[structure: benzene ring with $\mathrm{CH_3}$, OH and Br; OH and Br adjacent, $\mathrm{CH_3}$ para to OH]

Answer

[structure: benzene ring with $\mathrm{CH_3}$, OH and Br; Br adjacent to $\mathrm{CH_3}$, OH para to $\mathrm{CH_3}$]

JEE Main 8 April 2023, Shift 2, Chemistry Q76

Same idea in other shifts