The Third Step

You have brominated ortho-nitrotoluene. Since this compound has an ortho/para-directing group (methyl) oriented adjacent to a meta-directing group (nitro), two main products will result (formulas shown to the right). Examine these formulas carefully, noting that the methyl group is destined to become the carboxyl group.


Would either of these compounds be suitable precursors to the target molecule?

  4-bromo-2-nitrotoluene (on the left) would serve.
  2-bromo-6-nitrotoluene (on the right) would serve.
  Neither compound is suitable.

  Start again.