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1) Hg(OAc)2, H2O, THF 2) NaBH4
1) BH3, THF 2) H2O2, NaOH, H2O
HBr, ROOR, heat/light
HX, cold/dark
Br2
MCPBA
1) strong base 2) dilute acid
H+, HOR
Br2, HOR
1) BH3, THF 2) H2O2, NaOH, H2O
H2, Pt0 or Pd0
H2, Pt or Pd metal
H2, Ni2B or lindlar catalyst
Na0, NH3
PCC
KMnO4 or Na2CrO7/acid/water or CrO3/acid/water or PCC
KMnO4 or Na2CrO7/acid/water or CrO3/acid/water
1) OsO4 2) H2O2, NaHSO3
1) ozone 2) Zn, acetic acid
1) KMnO4 2) H3O/H2O
HX (excess), dark/cold
X2 (excess)
H2O, H2SO4, HgSO4
1) BH3, THF 2) H2O2, NaOH, H2O
NaNH2
H2O, H2SO4
HX
SOCl2 or PBr3
Nucleophile
NaOH or KOH
NaOR
NaNH2, RCH2LG
Weak base, ethanol, heat
Cl2, light
Br2, light