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HX (Hydrohogenation)
Markovnikov (H&X)
HBr, ROOR (Radical Addtion of HBr)
Anti-Markovnikov (H&Br)
H3O+ or [H2SO4] (Acid Catalyzed Hydration)
Markovnikov (H&OH)
1)Hg(OAc)2, H2O 2) NaBH4 (Oxymercuration-Dermercuration)
Markovnikov (H&OH)
1)BH3 • THF 2) H2O2, NaOH (Hydroboration-Oxidation)
Anti-Markovnikov (H&OH) Syn
H2, Pt (Catalytic Hydrogenation)
(H&OH) Syn
Br2 or Cl2 (Bromination or Chlorination)
(Br&Br) or (Cl&Cl) Anti
Br2, H2O (Halohudrin Formation)
OH to more substituted group (Br&OH) Anti
KMnO4 or OsO4 / NMO (Syn Dihydroxlyation)
(OH&OH) Syn
RCO3H (MCPBA) (Epoxidation)
(Epoxide) Anti
1) O3 2) DMS or Zn/H2O
(Cleave C=C, form two C=O groups)