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Pictures of the Day 4-18-07

Arenium ion
Shown above are models of the arenium ion produced during the chlorination of benzene. The chlorine atom is brown. As described by the electrostatic potential energy surface on the right, the positive charge (blue color) of the arenium ion is localized at the positions ortho and para to where the electrophile is attached. You should be able to draw resonance forms that predict the ortho and para distribution of the positive charge. This ortho and para distribution of positive charge is important because substituents already on an aromatic ring must interact with this charge distribution, and the result of that interaction is a modulation of rate and orientation of reaction. By understanding these interactions, you will be able to predict accurately the products of electrophilic substitution reactions that take place on aromatic rings containing substituents.