cat. ROOR Acid- catalyzed hydration Markovnikov addition Halogenation Catalytic Hydrogenation H2SO4, H2O Hydroboration- Oxidation 1)OsO4 2)NaHSO3, H2O HBr, HCl, HI Br2 or Cl2 Bromonium ion Pd, Pt Syn Addition Nucleophiles or Bases Halohydrin formation Syn Dihydroxylation 1) RCO3H 2) H3O+ 1) BH3, THF 2) NaOH, H2O2 Anti Addition Anti Dihydroxylation Halogen (Br + Cl) and H2O Epoxide Hydrohalogenation Anti- Markovnikov addition cat. ROOR Acid- catalyzed hydration Markovnikov addition Halogenation Catalytic Hydrogenation H2SO4, H2O Hydroboration- Oxidation 1)OsO4 2)NaHSO3, H2O HBr, HCl, HI Br2 or Cl2 Bromonium ion Pd, Pt Syn Addition Nucleophiles or Bases Halohydrin formation Syn Dihydroxylation 1) RCO3H 2) H3O+ 1) BH3, THF 2) NaOH, H2O2 Anti Addition Anti Dihydroxylation Halogen (Br + Cl) and H2O Epoxide Hydrohalogenation Anti- Markovnikov addition
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I-cat. ROOR
G-Acid-catalyzed hydration
I-Markovnikov addition
O-Halogenation
B-Catalytic Hydrogenation
G-H2SO4, H2O
I-Hydroboration-Oxidation
O-1)OsO4
2)NaHSO3, H2O
B-HBr, HCl, HI
O-Br2 or Cl2
I-Bromonium ion
O-Pd, Pt
G-Syn Addition
O-Nucleophiles or Bases
N-Halohydrin formation
I-Syn Dihydroxylation
N-1) RCO3H
2) H3O+
B-1) BH3, THF
2) NaOH, H2O2
B-Anti Addition
N-Anti Dihydroxylation
B-Halogen (Br + Cl) and H2O
G-Epoxide
G-Hydrohalogenation
N-Anti-Markovnikov addition