Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

Statement I: It is difficult to replace chlorine by –OH in chlorobenzene in comparison to that in chloroethane

Statement II: Chlorine – carbon (C–Cl) bond in chlorobenzene have double bond character due to resonance.

Options:

Both statement I and statement II are correct and statement II is the correct explanation of statement I

Both statement I and statement II are correct but statement II is not the correct explanation of statement I

Statement I is correct but statement II is false

Statement I is false but statement II is correct

Correct Answer:

Both statement I and statement II are correct and statement II is the correct explanation of statement I

Explanation:

The answer is (1) both statement I and statement II are correct and statement II is the correct explanation of statement I.

Statement I is correct because the chlorine-carbon bond in chlorobenzene has a partial double bond character due to resonance. This makes the chlorine atom less electronegative and less likely to be replaced by a nucleophile.

Statement II is also correct because the partial double bond character in the chlorine-carbon bond is caused by resonance. This means that statement II provides the reason for the decreased reactivity.

Here is a diagram that shows the resonance structures of chlorobenzene:

As you can see, the chlorine atom is sharing a pair of electrons with the benzene ring, giving the bond a partial double bond character. This makes the chlorine atom less electronegative and less likely to be replaced by a nucleophile.

Therefore, both statement I and statement II are correct and statement II is the correct explanation of statement I.