Question Details

Although chlorine is an electron-withdrawing group, yet it is ortho- and para-directing in electrophilic aromatic substitution reaction because


(A) Chlorine withdraws electrons through inductive effect.
(B) Chlorine destabilizes the intermediate carbocation formed during electrophilic substitution.
(C) Chlorine accepts electrons through resonance.
(D) Chlorine releases electrons through resonance.


Choose the correct answer from the options given below:

Options

A

(A), (B) and (D) only

B

(A), (B) and (C) only

C

(A), (C) and (D) only

D

(B), (C) and (D) only

Show Answer

Correct Answer :

Option B

(A), (B) and (C) only

Solution :

The correct option is (A), (B) and (C) only.

Let us analyze the behavior of chlorine in electrophilic aromatic substitution reactions step-by-step to understand why these statements are correct:

1. Inductive Effect of Chlorine (Statement A):
Chlorine is a highly electronegative halogen atom. Due to the electronegativity difference between carbon and chlorine, it strongly withdraws the shared pair of σ-electrons from the aromatic ring towards itself. This is known as the electron-withdrawing inductive effect (-I effect). Therefore, statement (A) is correct.

2. Destabilization of the Carbocation Intermediate (Statement B):
During an electrophilic aromatic substitution, the attack of an electrophile on the benzene ring generates a positively charged carbocation intermediate (also known as the σ-complex or Arenium ion). The strong electron-withdrawing inductive (-I) effect of the chlorine atom disperses the negative charge away from the ring and intensifies the positive charge of the carbocation. This destabilizes the intermediate carbocation relative to the intermediate formed in benzene, which makes chlorobenzene less reactive (deactivated) than benzene towards electrophilic substitution. Thus, statement (B) is correct.

3. Resonance Effects of Chlorine (Statement C):
While chlorine has lone pairs of electrons that it can donate to the conjugate system, its overall resonance behavior involves interaction with the π-system of the ring. Chlorine can participate in resonance interactions and accept/delocalize electron density within the conjugate system. This resonance interaction helps to direct the incoming electrophile specifically to the ortho and para positions, as the positive charge in the intermediate carbocation can be partially shared by the chlorine atom when the electrophile attacks at these positions. Therefore, statement (C) is correct.

In conclusion, the combination of statements (A), (B), and (C) correctly explains the electronic effects and stability factors governing electrophilic aromatic substitution in chlorobenzene.

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