Chapter 17, Problem 17.52SP

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.

1. a. 1-phenyl-1-bromobutane
2. b. 1-phenyl-1-methoxybutane
3. c. 3-phenylpropan-1-ol
4. d. ethoxybenzene
5. e. 1,2-dichloro-4-nitrobenzene
6. f. 1-phenylpropan-2-ol
7. g. p-aminobenzoic acid
8. h. 2-methyl-1-phenylbutan 2-ol
9. i. 5-chloro-2-methylaniline
10. j. 3-nitro-4-bromobenzoic acid
11. k. 3-nitro-5-bromobenzoic acid
12. l. 4-butylphenol
13. m. 2-(4-methylphenyl)butan-2-ol