List-I contains various reaction sequences and List-II contains different phenolic compounds. Match each entry in List-I with the appropriate entry in List-II and choose the correct option....

The correct option is (C). Click to read the detailed step-by-step conceptual solution.

JEE Advanced 2024 Paper 1 Chemistry Question 17 Solution

The reactions are summarized as follows:

(P) Benzene sulfonic acid reacts with molten $NaOH$ followed by $H_3O^+$ to give phenol. Phenol with concentrated $HNO_3$ yields 2,4,6-trinitrophenol (Picric acid). So, P $\rightarrow$ 3.
(Q) Nitrobenzene with $HNO_3/H_2SO_4$ gives m-dinitrobenzene. Reduction with $Sn/HCl$ gives m-phenylenediamine. Diazotization and hydrolysis results in resorcinol. Nitration of resorcinol with $HNO_3/H_2SO_4$ gives 2,4,6-trinitroresorcinol (Styphnic acid). So, Q $\rightarrow$ 5.
(R) Resorcinol with concentrated $H_2SO_4$ gives resorcinol-4,6-disulfonic acid (blocking the 4 and 6 positions). Nitration then occurs at the 2-position. Desulfonation with $H_3O^+$ and heat yields 2-nitroresorcinol. So, R $\rightarrow$ 4.
(S) Toluene is oxidized to benzoic acid. Heating with $HNO_3/H_2SO_4$ leads to dinitration forming 3,5-dinitrobenzoic acid. Conversion to amide followed by Hofmann Bromamide degradation gives 3,5-dinitroaniline. Diazotization and hydrolysis yields 3,5-dinitrophenol. So, S $\rightarrow$ 1. Correct Match: P-3, Q-5, R-4, S-1. Correct Option: C