Question Details

The major products obtained from the reactions in List-II are the reactants for the named reactions mentioned in List-I. Match each entry in List-I with the appropriate entry in List-II and choose the correct option.

List-I List-II
(P) Stephen reaction (1) (i) CrO₂Cl₂ / CS₂
    (ii) H₃O⁺
    Toluene →
(Q) Sandmeyer reaction (2) (i) PCl₅
    (ii) NH₃
    (iii) P₄O₁₀, Δ
    Benzoic acid →
(R) Hoffmann bromamide degradation reaction (3) (i) Fe, HCl
    (ii) HCl, NaNO₂ (273–278 K), H₂O
    Nitrobenzene →
(S) Cannizzaro reaction (4) (i) Cl₂ / hν, H₂O
    (ii) Tollens’ reagent
    (iii) SOCl₂
    (iv) NH₃
    Toluene →

(5) (i) (CH₃CO)₂O, Pyridine
    (ii) HNO₃, H₂SO₄, 288 K
    (iii) aq. NaOH
    Aniline →

Options

A

P → 2; Q → 4; R → 1; S → 3

B

P → 2; Q → 3; R → 4; S → 1

C

P → 5; Q → 3; R → 4; S → 2

D

P → 5; Q → 4; R → 2; S → 1

Show Answer

Correct Answer :

Option B

P → 2; Q → 3; R → 4; S → 1

Solution :

The correct option is: P → 2; Q → 3; R → 4; S → 1

Let us determine the major product for each reaction sequence in List-II and identify which named reaction in List-I uses that product as a reactant:

1. Analysis of reaction sequence (1):
Reactant: Toluene (C6H5-CH3)
Reagents: (i) CrO2Cl2 / CS2, followed by (ii) H3O+.
This sequence represents the Etard reaction. Toluene is oxidized to Benzaldehyde (C6H5-CHO).
Benzaldehyde undergoes the Cannizzaro reaction (S) because it is an aldehyde that lacks α-hydrogen atoms. Therefore, S → 1.

2. Analysis of reaction sequence (2):
Reactant: Benzoic acid (C6H5-COOH)
Reagents:
(i) PCl5 converts Benzoic acid to Benzoyl chloride (C6H5-COCl).
(ii) NH3 converts Benzoyl chloride to Benzamide (C6H5-CONH2).
(iii) P4O10, Δ is a strong dehydrating agent that dehydrates Benzamide to Benzonitrile (C6H5-CN).
Nitriles are the starting materials for the Stephen reaction (P) (reduction using SnCl2 / HCl followed by hydrolysis to form aldehydes). Therefore, P → 2.

3. Analysis of reaction sequence (3):
Reactant: Nitrobenzene (C6H5-NO2)
Reagents:
(i) Fe, HCl reduces Nitrobenzene to Aniline (C6H5-NH2).
(ii) HCl, NaNO2 (273–278 K) converts Aniline to Benzenediazonium chloride (C6H5-N2+Cl-).
Benzenediazonium chloride is the reactant for the Sandmeyer reaction (Q) (which yields chlorobenzene, bromobenzene, or benzonitrile upon reaction with copper(I) halides or copper(I) cyanide). Therefore, Q → 3.

4. Analysis of reaction sequence (4):
Reactant: Toluene (C6H5-CH3)
Reagents:
(i) Cl2 / hν converts Toluene to Benzyl chloride (C6H5-CH2Cl) and subsequent hydrolysis (H2O) yields Benzyl alcohol (C6H5-CH2OH).
(ii) Tollens' reagent oxidizes Benzyl alcohol to Benzoic acid (C6H5-COOH).
(iii) SOCl2 converts Benzoic acid to Benzoyl chloride (C6H5-COCl).
(iv) NH3 converts Benzoyl chloride to Benzamide (C6H5-CONH2).
Amides undergo the Hoffmann bromamide degradation reaction (R) when treated with Br2 and a base to yield primary amines. Therefore, R → 4.

Conclusion:
Matching the entries:
P → 2
Q → 3
R → 4
S → 1

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