Chapter 4.1, Problem 4.4P

Aromatic rings will also undergo iodination when treated with a suitable source of I⁺. There are many ways to form I⁺; you should look in your textbook and in your lecture notes to see if you are responsible for knowing how to iodinate benzene. If so, be aware that the mechanism is exactly the same as what we have seen. The only difference will be in the mechanism of how I⁺ is formed. Draw a mechanism for the reaction between benzene and I⁺ to form iodobenzene. In the first step of your mechanism, simply draw I⁺ as the electrophile (rather than a complex which delivers I⁺), and make sure to draw all resonance structures of the resulting sigma complex. Then, in the last step of your mechanism, use H₂O as the base that removes the proton to restore aromaticity (H₂O will be present for many of the methods that are used to prepare a source of I⁺).