As compared with chlorocyclohexane, which of the following statements correctly apply to chlorobenzene ?
A. The magnitude of negative charge is more on chlorine atoms
B. The C–Cl bond has partial double bond character
C. C–Cl bond is less polar
D. C–Cl bond is longer due to repulsion between delocalised electrons of the aromatic ring and lone pairs of electrons of chlorine.
E. The C–Cl bond is formed using hybridised orbital of carbon.
Choose the correct answer from the options given below :
- A
A, C and E only
- B
B, C and D only
- C
A, D and E only
- D
B, C and E only
Compare chlorobenzene with chlorocyclohexane.
A. Chlorine’s lone pair donates into the ring via resonance, so chlorobenzene’s Cl carries less negative charge than chlorocyclohexane’s. A is false.
B. Resonance delocalisation gives the aryl C–Cl bond partial double-bond character. True.
C. The opposing and effects partly cancel, so chlorobenzene is less polar overall than chlorocyclohexane. True.
D. Partial double-bond character actually shortens the bond — chlorobenzene’s C–Cl is shorter, not longer. D is false.
E. The aryl carbon bonded to Cl is hybridised. True.
Correct: B, C, E.
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