What are the 2 major products of the chlorination of the aromatic compound shown below?
There are two rings present in your napthalene molecule. One has a very strong electron withdrawer (NO2) on it, and one has a strong donor (OCH3). The iron in the solution will make your substitution electrophilic by pulling electron density toward the iron when the Cl2 coordinates through one chlorine atom. That leaves the other chlorine with a partial positive charge, making it an electrophile. Electron withdrawers function as meta directors in electrophilic substitution. if you look at the structure, however, both positions meta to the nitro group are unsubstitutable: one is a quaternary carbon, and the other is already occupied by a methyl group. That leaves the OCH3 side of the molecule. Being an electron donor, OCH3 is ortho-para directing in electrophilic reactions. Due to sterics, para substitution is always favored over ortho, if it is available. On your molecule, para substitution is not available. Both ortho positions are, though. One will have steric interaction with the me
