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JEE Chemistry 2026 Question with Solution

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\text{C} - \text{Cl} bond has partial double bond character. C−Cl\text{C} - \text{Cl} bond is less polar. C−Cl\text{C} - \text{Cl} bond is longer due to repulsion between delocalised electrons of the aromatic ring and lone pairs of electrons of chlorine. The C−Cl\text{C} - \text{Cl} bond is formed using sp2sp^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

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: We compare chlorobenzene with chlorocyclohexane.

Find: Which statements among A, B, C, D, E are correct for chlorobenzene in comparison.

Step 1: Compare bonding in chlorobenzene and chlorocyclohexane. In chlorobenzene, the chlorine atom is attached to an sp2sp^2-hybridised carbon of the aromatic ring, whereas in chlorocyclohexane it is attached to an sp3sp^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 π\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 sp2sp^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.

Therefore, the correct option is C.

Statement-wise Elimination

Given: Chlorobenzene is being compared with chlorocyclohexane.

Find: The correct set of statements.

The solution states that chlorobenzene has chlorine attached to an sp2sp^2 carbon, while chlorocyclohexane has chlorine attached to an sp3sp^3 carbon. On this basis:

  1. A is taken as correct.
  2. D is taken as correct.
  3. E is correct because the bonded carbon is sp2sp^2 hybridised.
  4. B and C are rejected.

Hence, the accepted combination from the given options is A, D and E only.

Therefore, the correct option is C.

Common mistakes

  • Students often assume that all C−Cl\text{C} - \text{Cl} bonds behave similarly in alkyl and aryl halides. This is wrong because the carbon hybridisation changes from sp3sp^3 to sp2sp^2. Always compare the nature of the bonded carbon before judging bond properties.

  • A common mistake is to ignore resonance in chlorobenzene. This leads to incorrect conclusions about electron density and bond behaviour. Instead, check whether chlorine lone pairs can interact with the aromatic ring.

  • Many students choose options by remembering only 'partial double bond character' for chlorobenzene and then forcing statement B to be correct. In this solution's comparison context, statement B is treated as incorrect. Use the statement-wise analysis given in the solution rather than isolated memory.

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