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.