In the reaction,the major product formed is:

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(A) The reactant is $N$-phenyl-isoindolin$-1-$one. In this molecule,the nitrogen atom is attached to a carbonyl group $(C=O)$,which is an electron-wit

Vedclass · Accepted Answer

Vedclass · Answer

(A) The reactant is $N$-phenyl-isoindolin$-1-$one. In this molecule,the nitrogen atom is attached to a carbonyl group $(C=O)$,which is an electron-withdrawing group. This makes the nitrogen atom less activating towards electrophilic aromatic substitution on the $N$-phenyl ring. However,the benzene ring fused to the isoindolinone structure is more electron-rich compared to the $N$-phenyl ring because the nitrogen's lone pair is delocalized into the carbonyl group,reducing its ability to activate the $N$-phenyl ring. Electrophilic aromatic substitution $(Br_2/Fe)$ will occur at the most activated position. The benzene ring of the isoindolinone system is more activated than the $N$-phenyl ring. Between the positions on the fused benzene ring,the position para to the alkyl group (the $CH_2$ group) is favored due to the ortho/para directing effect of the alkyl group. Thus,the bromine atom substitutes at the position shown in option $A$.

Similar Questions

What is heterolytic cleavage of a chemical bond?

Identify the product of the above rearrangement reaction.

The enol percentage of the following compound is maximum for:

Which statement is correct for the given reactions?

Heterolysis of $C-Cl$ bond produces:

Vedclass Test Series

Exam Paper Generator

Online Exam Module