General Organic ChemistryHard

Question

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

Choose the correct answer from the options given below:

Options

A.A, C and E only
B.B, C and D only
C.A, D and E only
D.B, C and E only

Solution

Chlorocylohexane is more polar due to -I effect of -Cl,

Whereas chlorobenzene has $- I > + M$, so it is less polar & also has partial double bond character.

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