Electrophilic Aromatic Substitution
For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry of the reaction (i.e., ortho- para- or meta-directing substituents).Click the mouse on the reactant molecule to view the answer;
click on the reagent to review the mechanism and regiochemistry of the reaction.
Chlorine in the presence of FeCl3 will result in the electrophilic addition of Cl+ to the aromatic ring. The methyl group is mildly activating and directs substitution ortho- and para-.
Bromine in the presence of FeBr3 will result in the electrophilic addition of Br+ to the aromatic ring. The sulfonic acid group is deactivating and directs substitution meta-.
Iodine in the presence of CuCl2 will result in the electrophilic addition of I+ to the aromatic ring. The nitro group is strongly deactivating and directs substitution meta-.
SO3 in the presence of H2SO4 will result in the electrophilic addition of SO3+ to the aromatic ring. The chloro group is mildly deactivating but directs substitution ortho- and para- through resonance interactions with the ring.
Chlorine in the presence of FeCl3 will result in the electrophilic addition of Cl+ to the aromatic ring. The methyl group is mildly activating and directs substitution ortho- and para-.
Bromine in the presence of FeBr3 will result in the electrophilic addition of Br+ to the aromatic ring. The sulfonic acid group is deactivating and directs substitution meta-.
Iodine in the presence of CuCl2 will result in the electrophilic addition of I+ to the aromatic ring. The nitro group is strongly deactivating and directs substitution meta-.
SO3 in the presence of H2SO4 will result in the electrophilic addition of SO3+ to the aromatic ring. The chloro group is mildly deactivating but directs substitution ortho- and para- through resonance interactions with the ring.