This experiment allows students to use [to the first power]H NMR to directly compare the relative initial rates of substitution of the benzylic and non-benzylic [alpha] hydrogens of [beta]-tetralone and correlate their findings with the predictions made by resonance theory. The experiment demonstrates that the benzylic hydrogens undergo [alpha] substitution much faster than the non-benzylic hydrogens. The described experiment can be used in the introductory two-semester organic chemistry course sequence to make the concepts of enolization and resonance concrete. (Contains 2 schemes and 2 figures.)