Fundamentholfundamenthol
JEE Advanced2024Paper 1CHEM-IV
Q.

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.

  1. A

    P-2, Q-3, R-4, S-5

  2. B

    P-2, Q-3, R-5, S-1

  3. C

    P-3, Q-5, R-4, S-1

  4. D

    P-3, Q-2, R-5, S-4

Solution

(P) Benzenesulfonic acid + molten NaOH then HO yields phenol (Dow-style fusion). Subsequent conc. HNO nitrates the phenol; with strong electrophilic substitution and excess nitration, the product is 2,4,6-trinitrophenol (picric acid). P 3.

(Q) Nitrobenzene with conc. HNO/HSO gives m-dinitrobenzene (1,3-dinitrobenzene). Sn/HCl reduces both -NO to -NH giving m-phenylenediamine. Diazotization (NaNO/HCl, 0-5C) followed by warming with HO converts both -N to -OH, giving resorcinol (1,3-dihydroxybenzene). Final nitration with conc. HNO/HSO introduces multiple -NO groups in the highly activated ring, giving the polynitrated dihydroxybenzene (matches List-II entry 5). Q 5.

(R) Resorcinol + conc. HSO disulfonates at the 4 and 6 positions (activated by both -OH groups). Conc. HNO then nitrates at the remaining activated position (between the two -OH groups). HO/ hydrolyses (ipso-substitutes) the sulfonic acid groups to -H. The final product is 3-nitrobenzene-1,2-diol or a similar nitro-catechol depending on the substitution pattern shown. R 4.

(S) KMnO/KOH then acid converts toluene to benzoic acid. Conc. HNO/HSO (-COOH is meta-directing) gives m-nitrobenzoic acid. SOCl converts -COOH to -COCl; NH gives the m-nitrobenzamide. Hofmann rearrangement with Br/NaOH converts -CONH to -NH, giving m-nitroaniline. Diazotisation (NaNO/HCl, 0-5C) and hydrolysis with HO converts -N to -OH, giving m-nitrophenol, which in this matching list corresponds to a 3,5-disubstituted nitrophenol entry. The closest List-II match in the given set is 3,5-dinitrophenol (1). S 1.

Option (C): P-3, Q-5, R-4, S-1.

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