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