Hydrocarbons Question 234

Question: Arrange in order of decreasing trend towards electrophilic substitution reactions: Chlorobenzene (I), benzene (II), toluene (III), anilinium chloride (IV)

Options:

A) III > II > I > IV

B) IV > I > II > III

C) II > I > IV > III

D) I > II > IV > III

Show Answer

Answer:

Correct Answer: A

Solution:

[a] The order of decreasing trend towards reaction is Toluene > Benzene > Chlorobenzene > Anilinium chloride.

Due to the -I effect, chlorobenzene is less reactive than benzene in electrophilic substitution reactions.

Since chlorine is an electron-withdrawing group, it deactivates the benzene ring, lowers its electron density, and lessens its reactivity toward incoming electrophiles.