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In multi-substituted benzenes, both substituents affect regioselectivity. Benzene’s aromatic stability (approximately 36 kcal/mol of resonance stabilization) means it doesn’t bear addition like strange alkenes. Epoxidation with mCPBA followed by acid-catalyzed ring opening additionally offers anti addition overall. Halogenation of alkenes proceeds by way of a cyclic bromonium ion, giving anti addition — the 2 bromines find yourself on opposite faces. Hydration, HX addition, and oxymercuration-demercuration all comply with Markovnikov regiochemistry. The ratio of substitution to elimination product will increase with temperature for E1/SN1 methods and with base focus for E2/SN2 systems.
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