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Question 58

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 $$ sp^{2} $$ hybridised orbital of carbon.

Choose the correct answer from the options given below:

We need to identify which statements correctly describe chlorobenzene compared to chlorocyclohexane.

Statement A: "The magnitude of negative charge is more on chlorine atom."

In chlorobenzene, the C-Cl bond is less polar due to resonance effect (back-donation of lone pairs of Cl into the ring). This means the negative charge on Cl is less in chlorobenzene compared to chlorocyclohexane. Statement A is false.

Statement B: "The C-Cl bond has partial double bond character."

Due to resonance, the lone pair on Cl delocalizes into the benzene ring, giving the C-Cl bond partial double bond character. Statement B is true.

Statement C: "C-Cl bond is less polar."

Due to the $$sp^2$$ carbon being more electronegative than $$sp^3$$ carbon, and due to resonance, the C-Cl bond in chlorobenzene is less polar. Statement C is true.

Statement D: "C-Cl bond is longer due to repulsion between delocalised electrons and lone pairs."

Actually, the C-Cl bond in chlorobenzene is shorter than in chlorocyclohexane due to partial double bond character and the $$sp^2$$ carbon having a smaller atomic radius. Statement D is false.

Statement E: "The C-Cl bond is formed using $$sp^2$$ hybridised orbital of carbon."

In chlorobenzene, the carbon attached to Cl is $$sp^2$$ hybridized (part of the benzene ring), while in chlorocyclohexane it is $$sp^3$$. Statement E is true.

The correct statements are B, C, and E, which matches Option D.

Therefore, the answer is Option D.

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