Question:
Which of the following compounds has difficulty in breaking of C $-$ X bond?
Which of the following compounds has difficulty in breaking of C $-$ X bond?
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Presence of electron-withdrawing groups ($-NO_2$, $-CN$) at ortho/para positions makes aryl halides more reactive (easier to break $C-X$).
Updated On: Apr 30, 2026
- o-Nitrochlorobenzene
- m-Nitrochlorobenzene
- p-Nitrochlorobenzene
- Chlorobenzene
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The Correct Option is D
Solution and Explanation
Step 1: Concept
The $C-Cl$ bond in aryl halides is difficult to break due to partial double bond character (resonance) and $sp^2$ hybridization of carbon.
Step 2: Effect of Substituents
Electron-withdrawing groups (EWG) like $-NO_2$ at ortho or para positions increase the reactivity towards nucleophilic substitution by stabilizing the intermediate carbanion.
Step 3: Analysis
- Options (A), (B), and (C) have an activating $-NO_2$ group that facilitates bond breaking. - Chlorobenzene (implied as the base case) has the most "difficulty" because it lacks these activating groups.
Step 4: Conclusion
Unsubstituted chlorobenzene has the strongest $C-X$ bond among the choices.
Final Answer:(D)
The $C-Cl$ bond in aryl halides is difficult to break due to partial double bond character (resonance) and $sp^2$ hybridization of carbon.
Step 2: Effect of Substituents
Electron-withdrawing groups (EWG) like $-NO_2$ at ortho or para positions increase the reactivity towards nucleophilic substitution by stabilizing the intermediate carbanion.
Step 3: Analysis
- Options (A), (B), and (C) have an activating $-NO_2$ group that facilitates bond breaking. - Chlorobenzene (implied as the base case) has the most "difficulty" because it lacks these activating groups.
Step 4: Conclusion
Unsubstituted chlorobenzene has the strongest $C-X$ bond among the choices.
Final Answer:(D)
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