In the described experiment, the regiochemical outcome of the addition of "HOBr" to [alpha]-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization [to the thirteenth power]C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition. As expected, 1-bromo-2-phenyl-2-propanol is the major product from the reaction of [alpha]-methylstyrene and N-bromosuccinimide in 95% acetone (aq). (Contains 1 scheme.)