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