When methyloxirane is treated with HBr, the bromide ion
Chapter 14, Problem 14.58(choose chapter or problem)
When methyloxirane is treated with HBr, the bromide ion attacks the less substituted position. However, when phenyloxirane is treated with HBr, the bromide ion attacks the more substituted position. O Me HO Me Br HBr O Ph OH Br Ph HBr Explain the difference in regiochemistry in terms of a competition between steric effects and electronic effects. (Hint: It may help to draw out the structure of the phenyl group.)
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