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? |
Toluene o-Chlorotoluene m-Chlorotoluene p-Chlorotoluene |
o-Chlorotoluene |
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. |