Prepare the following compounds from benzene:

statements

SOLUTION:

solution-problem-benzene-01

Another possible solution is to alkylate with methyl iodide and halogenate with NBS.

solution-problem-benzene-02

The Friedl-Crafts acylation reaction introduces the acetyl group into benzene.

solution-problem-benzene-03

We can also introduce the acid group by diazotization followed by Sandmeyer.