Question:
Which of the following has highest reactivity towards nucleophilic substitution reaction involving cleavage of C — Cl bond?
Which of the following has highest reactivity towards nucleophilic substitution reaction involving cleavage of C — Cl bond?
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Reactivity $\propto$ Number of Electron Withdrawing Groups ($-\text{NO}_2$, $-\text{CN}$) at ortho and para positions.
Updated On: Apr 26, 2026
- Chlorobenzene
- p-Nitrochlorobenzene
- 2,4-Dinitrochlorobenzene
- 2,4,6-Trinitrochlorobenzene
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The Correct Option is D
Solution and Explanation
Step 1: Concept
Aryl halides are generally inert to nucleophilic substitution. However, the presence of Electron Withdrawing Groups (EWG) like $-\text{NO}_2$ at ortho and para positions increases reactivity.
Step 2: Analysis
- (A) has no EWG. - (B) has one $-\text{NO}_2$ group. - (C) has two $-\text{NO}_2$ groups. - (D) has three $-\text{NO}_2$ groups (at 2, 4, and 6 positions).
Step 3: Conclusion
The greater the number of electron-withdrawing nitro groups at ortho/para positions, the easier it is for the nucleophile to attack the benzene ring.
Final Answer: (D)
Aryl halides are generally inert to nucleophilic substitution. However, the presence of Electron Withdrawing Groups (EWG) like $-\text{NO}_2$ at ortho and para positions increases reactivity.
Step 2: Analysis
- (A) has no EWG. - (B) has one $-\text{NO}_2$ group. - (C) has two $-\text{NO}_2$ groups. - (D) has three $-\text{NO}_2$ groups (at 2, 4, and 6 positions).
Step 3: Conclusion
The greater the number of electron-withdrawing nitro groups at ortho/para positions, the easier it is for the nucleophile to attack the benzene ring.
Final Answer: (D)
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