Question: 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

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.

Explain the difference in regiochemistry in terms of a competition between steric effects and electronic effects.

Ph. HBr HBr Me Me Br Br Ph

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