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