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