Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

Haloarenes undergo the usual electrophilic reactions of the benzene ring such as halogenation, nitration, sulphonation and Friedel-Crafts reactions. Halogen atom besides being slightly deactivating is o, p-directing; therefore, further substitution occurs at ortho- and para-positions with respect to the halogen atom. Due to resonance, the electron density increases more at ortho- and para-positions than at meta-positions. Further, the halogen atom because of its –I effect has some tendency to withdraw electrons from the benzene ring. As a result, the ring gets somewhat deactivated as compared to benzene and hence the electrophilic substitution reactions in haloarenes occur slowly and require more drastic conditions as compared to those in benzene.

Predict the minor product formed when chlorobenzene reacts with chloromethane in the presence of anhydrous AlCl3?

Options:

Toluene

o-Chlorotoluene

m-Chlorotoluene

p-Chlorotoluene

Correct Answer:

o-Chlorotoluene

Explanation:

The correct answer is option 2. o-Chlorotoluene.

When chlorobenzene reacts with chloromethane in the presence of anhydrous aluminum chloride \((AlCl_3)\), a Friedel-Crafts alkylation reaction occurs. The major product will be the para-substituted product, p-Chlorotoluene, due to the directing effects of the chlorine atom. The minor product will be the ortho-substituted product, o-Chlorotoluene, due to steric hindrance making it less favorable compared to the para position.

So, the correct answer for the minor product is o-Chlorotoluene.