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. |
What is the major product formed when chlorobenzene reacts with a molecule of chlorine? |
1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 1,2,4-Trichlorobenzene |
1,4-Dichlorobenzene |
The correct answer is option 3. 1,4-Dichlorobenzene. When chlorobenzene reacts with chlorine in the presence of a catalyst like iron(III) chloride \((FeCl_3)\), the major product is 1,4-Dichlorobenzene. Chlorine is an ortho/para-directing group due to its electron-donating resonance effect, despite being a deactivating group overall because of its electron-withdrawing inductive effect. The para position is favored over the ortho position due to reduced steric hindrance. So, the correct answer is 1,4-Dichlorobenzene. |