A relatively simple experimental set up allows for both a free radical bromination of tetralin and addition of hydrogen bromide to 3,3-dimethyl-1-butene to be simultaneously carried out. Both reactions had, for the students, unexpected outcome with the major products being naphthalene, 1-bromonaphthalene and 1,4-dibromonaphthalene while addition of hydrogen bromide to 3,3-dimethyl-1-butene gave as the major reaction product either 1-bromo-3,3-dimethylbutane or 2-bromo-2,3-dimethylbutane, depending on the reaction conditions. Students were provided with description of the reaction outcome from different literature sources and asked to evaluate them.
Soto et al. (Mon,) studied this question.