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JEE Advanced 2026Paper 2
Exam
JEE Advanced
Year
2026
Paper
Paper 2
Subject
Chemistry
Chapter
Amines

JEE Advanced 2026 · Paper 2 · Chemistry · Amines

In the following reaction sequence, P , Q , S and T are the major...

In the following reaction sequence, P\textbf{P}, Q\textbf{Q}, S\textbf{S} and T\textbf{T} are the major products.
In the following reaction sequence, P , Q , S and T are the major products. The correct statement(s) about P , Q , S
The correct statement(s) about P\textbf{P}, Q\textbf{Q}, S\textbf{S} and T\textbf{T} is(are)

Options

  1. AQ\textbf{Q} on treatment with ethanol generates an aromatic aldehyde.
  2. BS\textbf{S} gives positive phthalein dye test.
  3. CP\textbf{P} is a dinitro compound.
  4. DT\textbf{T} is a coloured compound.

Correct answer

B. S\textbf{S} gives positive phthalein dye test.

Step-by-step solution

In the first reaction sequence:
Step 1: Aniline reacts with acetic anhydride in the presence of pyridine to undergo acetylation, forming acetanilide.
Step 2: Acetanilide is treated with a nitrating mixture (conc. HNO3\text{HNO}_3 and conc. H2SO4\text{H}_2\text{SO}_4) at 288 K288 \text{ K}. The −NHCOCH3-\text{NHCOCH}_3 group is moderately activating and ortho/para directing. Due to steric hindrance, the major product P\textbf{P} is pp-nitroacetanilide.
Step 3: P\textbf{P} is hydrolyzed with H3O+\text{H}_3\text{O}^+ to yield pp-nitroaniline.
Step 4: pp-nitroaniline is diazotized using NaNO2/HCl\text{NaNO}_2/\text{HCl} at 273−278 K273-278 \text{ K} to form the diazonium salt Q\textbf{Q}, which is pp-nitrobenzenediazonium chloride.

In the second reaction sequence:
Step 1: Cumene (isopropylbenzene) is oxidized by O2\text{O}_2 followed by acid hydrolysis (H3O+\text{H}_3\text{O}^+) to produce phenol and acetone. The major aromatic product is phenol.
Step 2: Phenol undergoes the Kolbe-Schmitt reaction with NaOH\text{NaOH} and CO2\text{CO}_2 to form sodium salicylate.
Step 3: Acidification with H3O+\text{H}_3\text{O}^+ yields salicylic acid as the major product S\textbf{S}.

In the final reaction:
Salicylic acid (S\textbf{S}) reacts with pp-nitrobenzenediazonium chloride (Q\textbf{Q}) in an aqueous NaOH\text{NaOH} medium. This is an electrophilic aromatic substitution (azo coupling). The phenoxide ion formed is highly activating, and coupling occurs at the para position with respect to the −OH-\text{OH} group (position 5 of salicylic acid). The resulting product T\textbf{T} is an azo dye, which is a highly conjugated and coloured compound.

Evaluating the options:
(A) Treatment of Q\textbf{Q} (pp-nitrobenzenediazonium chloride) with ethanol reduces the diazonium group, yielding nitrobenzene, not an aromatic aldehyde. (Incorrect)
(B) The phthalein dye test is a characteristic test for phenols. Salicylic acid (S\textbf{S}) contains a phenolic −OH-\text{OH} group with a free para position (position 5) and gives a positive phthalein dye test when heated with phthalic anhydride and conc. H2SO4\text{H}_2\text{SO}_4. (Correct)
(C) P\textbf{P} is pp-nitroacetanilide, which is a mononitro compound, not a dinitro compound. (Incorrect)
(D) T\textbf{T} is an azo dye, which is a coloured compound. (Correct)

Answer: S\textbf{S} gives positive phthalein dye test.; T\textbf{T} is a coloured compound.
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