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chem 249 sac jenkins
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HBr or HCl or HI, -30 deg C
or
HBr + ROOR(peroxide)
Hydrohalogenation
1) H3O+ 2) H2SO4
Acid Catalyzed Hydration
1) Hg(OAc)2, Nuc 2) NaBH4
Oxymercuration-Demurcuration
1) BH3 * THF 2) H2O2, NaOH
Hydroboration Oxidation
H2, Pd or Pt or Ni
Catalytic Hydrogenation
Br2 or Cl2
Halogenation
Br2 or Cl2, H2O
Halohydrin Formation
1) mCPBA or RCO3H 2) H3O+ or H2SO4
anti-Dihydroxylation
OsO4(catalytic), NMO
or
OsO4, NaHSO3/H2O or Na2SO3/H2O
or
KMnO4, NaOH, cold temp
syn-Dihydroxylation
1) O3 2) DMS
Oxidative Cleavage