HCl, HBr, H3O+, 1. Br2 / 2. CH2Cl2, Cl2, H2O, 1. H2 / 2. Pd, 1. Hg(OAc)2, H2O / 2. NaBH4, 1. BH3 / 2. H2O2, NaOH, 1. OsO4 / 2. NaHSO4, H2O, 1. O3 / 2. (CH3)2S

pentene reaction

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