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Preferred Site for Electrophilic Attack on Given Aromatic Molecule

For the given molecule, "xx", the preferred site for the attack of the electrophile is :

Question Diagram 1

Options

A

Predominantly at "rr"

B

"rr" and "uu"

C

"pp" and "ss"

D

Predominantly at "uu"

Correct

Step-by-Step Solution

To determine the preferred site for electrophilic aromatic substitution in the molecule xx (benzanilide, Ph-CO-NH-Ph\text{Ph-CO-NH-Ph}), we analyze the electronic effects of the substituents on both aromatic rings:

  1. Comparison of Ring Activation:

    • Benzoyl Ring (containing sites rr and pp): This ring is directly attached to the carbonyl group (C(=O)-\text{C(=O)}-). The carbonyl group acts as an electron-withdrawing group via resonance (M-M) and inductive effects (I-I). As a result, this ring is deactivated toward electrophilic aromatic substitution.
    • Anilidic Ring (containing sites ss and uu): This ring is directly attached to the nitrogen atom (NH-\text{NH}-). The lone pair of electrons on the nitrogen atom can undergo resonance with the π\pi-system of the benzene ring (+M+M effect), significantly increasing the electron density. Thus, this ring is strongly activated toward electrophilic aromatic substitution relative to the benzoyl ring.
  2. Regioselectivity on the Activated Ring:

    • The NH-CO-Ph-\text{NH-CO-Ph} group is an ortho/para-directing group.
    • Position ss corresponds to the ortho position relative to the NH-CO-Ph-\text{NH-CO-Ph} group.
    • Position uu corresponds to the para position relative to the NH-CO-Ph-\text{NH-CO-Ph} group.
    • Due to the bulky nature of the NH-CO-Ph-\text{NH-CO-Ph} group, the ortho position (ss) experiences significant steric hindrance.
    • Therefore, electrophilic attack occurs with high selectivity at the sterically unhindered para position (uu).

Thus, the preferred site for the attack of the electrophile is predominantly at "uu".

Correct Option: D (Predominantly at "uu")

Preferred Site for Electrophilic Attack on Given Aromatic Molecule | Chemistry PYQ Solution - JEE Challenger