Chapter 23, Problem 23.14YT

Interpretation Introduction

Interpretation:

Whether you can reorder the steps in the synthesis in Equation 23-48 to produce $\text{m-nitrobenzoic acid}$ instead is to be determined.

Concept introduction:

The ${\text{CO}}_{\text{2}}\text{H}$ group is a meta directing group, so the oxidation of the alkyl group prior to nitration will direct the ${\text{NO}}_{\text{2}}$ group meta. In the nitration of benzene ring, the ring would be deactivated enough that Friedel-Crafts alkylation would not occur.