Question

As compared with chlorocyclohexane, which of the following statements correctly apply to chlorobenzene?
The magnitude of negative charge is more on chlorine atom.
The C--Cl bond has partial double bond character.
C--Cl bond is less polar.
C--Cl bond is longer due to repulsion between delocalised electrons of the aromatic ring and lone pairs of electrons of chlorine.
The C--Cl bond is formed using \(sp^2\) hybridised orbital of carbon.
Choose the correct answer from the options given below:

• A. B, C and D Only
• B. A, C and E Only
• C. A, D and E Only
• D. B, C and E Only

Hint:

In chlorobenzene, resonance and \(sp^2\) hybridisation significantly affect bond polarity and bond length.

Answer 1

The Correct Option is C

Step 1: Compare bonding in chlorobenzene and chlorocyclohexane.
In chlorobenzene, the chlorine atom is attached to an \(sp^2\)-hybridised carbon of the aromatic ring, whereas in chlorocyclohexane it is attached to an \(sp^3\)-hybridised carbon.
Step 2: Analyse each statement.
Statement A is correct because resonance donation of lone pairs increases negative charge density on chlorine.
Statement D is correct because repulsion between delocalised \(\pi\)-electrons of benzene and lone pairs of chlorine increases bond length.
Statement E is correct as the carbon atom bonded to chlorine in chlorobenzene is \(sp^2\)-hybridised.
Statements B and C are incorrect in this comparison context.
Step 3: Conclude the correct combination.
Thus, the correct statements are A, D and E only.
Final Answer: \[ \boxed{\text{A, D and E Only}} \]