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 → |
Correct Answer :
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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