Chlorobenzene vs Chlorocyclohexane C–Cl Bond | JEE Main Organic Chemistry
As compared with chlorocyclohexane, which of the following statements correctly apply to chlorobenzene?

A. The magnitude of negative charge is more on chlorine atom.
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 sp2 hybridised orbital of carbon.
A. B, C and E Only
B. A, C and E Only
C. B, C and D Only
D. A, D and E Only
Correct Answer: B, C and E Only

Detailed Explanation

In chlorobenzene, chlorine has lone pair electrons which participate in resonance with the benzene ring.

Statement A: False
Due to resonance donation (+R effect), electron density is delocalised over the ring. Hence, the magnitude of negative charge on chlorine is less than in chlorocyclohexane.

Statement B: True
The C–Cl bond in chlorobenzene has partial double bond character due to resonance between chlorine lone pair and aromatic π electrons.

Statement C: True
Due to partial double bond character, the C–Cl bond in chlorobenzene is less polar compared to chlorocyclohexane.

Statement D: False
The C–Cl bond in chlorobenzene is actually shorter, not longer, because partial double bond character reduces bond length.

Statement E: True
In chlorobenzene, carbon is part of aromatic ring and is therefore sp2 hybridised.

Hence, the correct statements are B, C and E only.

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