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