Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of alpha-Methylstyrene

In the described experiment, the regiochemical outcome of the addition of "HOBr" to α-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C 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 α-methylstyrene and N-bromosuccinimide in 95% acetone (aq).