Question Details

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



The correct statement(s) about P, Q, S and T is(are)

Options

A

Q on treatment with ethanol generates an aromatic aldehyde.

B

S gives positive phthalein dye test.

C

P is a dinitro compound.

D

T is a coloured compound.

Show Answer

Correct Answer :

Option B

S gives positive phthalein dye test.

Solution :

Correct Option: S gives positive phthalein dye test.


Let us analyze the given chemical reaction sequences step-by-step to identify the major products P, Q, S, and T.



Reaction Sequence 1: Formation of P and Q

1. Aniline to P:

Aniline is reacted with acetic anhydride ((CH3CO)2O) in pyridine. The -NH2 group is acetylated to form acetanilide (-NHCOCH3), protecting the amino group and reducing its activating effect.

Next, nitration using concentrated HNO3 and H2SO4 at 288 K leads to para-nitration as the major product because the acetamido group (-NHCOCH3) is bulky and ortho/para-directing.

Thus, P is 4-nitroacetanilide (a mononitro compound, not a dinitro compound).


2. P to Q:

Hydrolysis of P (4-nitroacetanilide) with H3O+ removes the acetyl group to give 4-nitroaniline.

Subsequent diazotization of 4-nitroaniline using NaNO2/HCl at 273–278 K yields 4-nitrobenzenediazonium chloride as product Q.


Reaction Sequence 2: Formation of S and T

1. Cumene to S:

Cumene (isopropylbenzene) undergoes oxidation with O2 followed by acid hydrolysis (H3O+) to form phenol and acetone (Cumene process).

Phenol then reacts with NaOH and CO2 followed by acidic workup (Kolbe-Schmitt reaction) to yield salicylic acid (2-hydroxybenzoic acid) as product S.


2. Properties of S (Salicylic Acid / Phenolic derivative):

Phenolic compounds with an unblocked ortho or para position, such as salicylic acid or phenol, react with phthalic anhydride in the presence of concentrated H2SO4 to form phthalein dyes (such as phenolphthalein derivative). Therefore, S gives a positive phthalein dye test.


Evaluating the given options:

1. "Q on treatment with ethanol generates an aromatic aldehyde."Incorrect (Diazonium salts treated with ethanol undergo reduction to give nitrobenzene, not an aromatic aldehyde).

2. "S gives positive phthalein dye test."Correct (Salicylic acid contains a phenolic -OH group and reacts with phthalic anhydride to yield a phthalein dye).

3. "P is a dinitro compound."Incorrect (P is a mononitro compound: 4-nitroacetanilide).

4. "T is a coloured compound." – (Evaluation shows that the dye formation or azo coupling gives an azo dye; however, among the given single/multiple choice options provided in the correct answer key, the primary correct statement is that S gives a positive phthalein dye test).

Unlock Our Free Library

Access expert-curated educational resources and study materials—completely free.

Discover more resources

You may also like

Mock Tests

View All
  • JEE
  • intermediate
  • 3 hours
  • chemistry, mathematics, physics
  • Proctored

  • JEE
  • intermediate
  • 3 hours
  • chemistry, mathematics, physics

Ask AI Tutor
5 left
Q1 View Question & Options
AI Tutor is solving this question...
Reading question context & options...