The substitution reaction of toluene with Br2 can, in principle, lead to the formation

Chapter 15, Problem 15.50

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The substitution reaction of toluene with Br2 can, in principle, lead to the formation of three isomeric bromotoluene products. In practice, however, only o- and p-bromotoluene are formed in substantial amounts. The meta isomer is not formed. Draw the structures of the three possible carbocation intermediates ( 15.49), and explain why ortho and para products predominate over meta.

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