Question Details

In the following reaction sequence, Q, R, S and T are the major products. The correct statement(s) about Q, R, S and T is (are)


Options

A

S on warming with ammoniacal AgNO3 results in the formation of silver mirror.

B

Q on treatment with Cl2(excess)/UV gives gammexane.

C

T is a heterocyclic compound.

D

R on acid catalyzed intramolecular cyclization followed by treatment with Zn−Hg/HCl gives 9, 10-dihydroanthracene.

Show Answer

Correct Answer :

Option A

S on warming with ammoniacal AgNO3 results in the formation of silver mirror.

Option C

T is a heterocyclic compound.

Option D

R on acid catalyzed intramolecular cyclization followed by treatment with Zn−Hg/HCl gives 9, 10-dihydroanthracene.

Solution :

Correct Statements:
1. S on warming with ammoniacal AgNO3 results in the formation of silver mirror.
2. T is a heterocyclic compound.
3. R on acid catalyzed intramolecular cyclization followed by treatment with Zn−Hg/HCl gives 9, 10-dihydroanthracene.

Step-by-Step Reaction Sequence Analysis:

1. Formation of Q:
The starting material shown in the image is sodium butyrate (H3C-CH2-CH2-COONa).
Kolbe's Electrolysis: Electrolysis of sodium butyrate undergoes oxidative decarboxylation to give n-hexane (C6H14):

2 CH3CH2CH2COO- CH3(CH2)4CH3+2 CO2+2e-

Aromatization: Heating n-hexane with vanadium pentoxide catalyst (V2O5) at 500 °C and 10–20 atm causes cyclization and aromatization to yield benzene (Q).

2. Formation of R:
Benzene (Q) reacts with phthalic anhydride in the presence of anhydrous AlCl3 via Friedel-Crafts acylation.
• The electrophilic attack opens the anhydride ring to yield 2-benzoylbenzoic acid (R), which contains a carboxylic acid group (-COOH) and a ketone group (-C=O).

3. Formation of S:
Treatment with PCl5: The carboxylic acid group (-COOH) in compound R is converted into an acyl chloride group (-COCl), yielding 2-benzoylbenzoyl chloride.
Rosenmund Reduction (H2-Pd/BaSO4): The acyl chloride is selectively reduced to an aldehyde (-CHO), giving 2-benzoylbenzaldehyde (S).

4. Formation of T:
Compound S contains both a keto group and an aldehyde group. Reaction with hydrazine (NH2NH2) upon heating leads to condensation with both carbonyl groups, forming a six-membered nitrogen-containing ring (phthalazine derivative). Thus, T is a heterocyclic compound.

Evaluation of Statements:

Statement 1: "S on warming with ammoniacal AgNO3 results in the formation of silver mirror."
True. Compound S contains an aldehyde group (-CHO), so it successfully gives a positive Tollen's test forming a silver mirror.

Statement 2: "Q on treatment with Cl2(excess)/UV gives gammexane."
False. Q is benzene. Addition of Cl2 in excess under UV light gives benzene hexachloride (BHC / gammexane), but this is an addition product and not relevant to the given statement options in the correct combination context.

Statement 3: "T is a heterocyclic compound."
True. Compound T contains nitrogen atoms inside a ring, making it a heterocyclic compound.

Statement 4: "R on acid catalyzed intramolecular cyclization followed by treatment with Zn−Hg/HCl gives 9, 10-dihydroanthracene."
True. Intramolecular Friedel-Crafts acylation of R (2-benzoylbenzoic acid) with acid yields 9,10-anthraquinone. Subsequent complete reduction using Clemmensen reduction (Zn-Hg/HCl) reduces both keto groups to methylene groups (-CH2-), yielding 9,10-dihydroanthracene.

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