An experiment is described involving the nitration of ortho or meta monosubstituted benzoic acids (XC[subscript 6]H[subscript 4]CO[subscript 2]H, X = Halogen, Me, OH, or OMe) and monochlorinated acetanilides with nitric acid to determine the regioselectivity of addition by [superscript 1]H NMR spectroscopy and molecular modeling. Students were able to interpret the [superscript 1]H NMR spectra regardless of the formation of multiple products or contamination from the starting materials. With one exception, both the [superscript 1]H NMR spectroscopy and computational methods agreed with the theoretical expectation and provided a nice demonstration of regioselectivity of nitration on substituted benzene. (Contains 2 tables, 1 figure and 1 note.)