Studied by 91 peoplelist the reagents that will give this product
1) Hg(OAc)2, H2O, THF 2) NaBH4
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1) Hg(OAc)2, HOR, THF 2) NaBH4
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1) BH3, THF 2) H2O2, NaOH, H2O
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HBr, peroxides (ROOR), heat or light
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HX, cold, dark, no peroxides
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Br2
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MCPBA
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1) strong base 2) dilute acid
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H+, HOR
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Br2, HOR
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CHCl3, KOH
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CH2I2, Zn(Cu)
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1) BH3, THF 2) H2O2, NaOH, H2O
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H2, Pt or Pd
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H2, Pt or Pd
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H2, Ni2B or H2, Lindlar Catalyst
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Na, NH3 (l)
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PCC
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KMnO4 or Na2Cr2O7, acid, water or CrO3, acid, water or PCC
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KMnO4 or Na2Cr2O7, acid, water or CrO3, acid, water
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1) OsO4 2) H2O2 or NaHSO3
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1) O3 2) Zn, HOAc
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1) KMnO4 (hot) 2) H3O+, H2O
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1) HX, dark, cold, no peroxides 2) HX, dark, cold, no peroxides
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1) X2 2) X2
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H2O, H2SO4, HgSO4
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1) BH3, THF 2) H2O2, NaOH, H2O
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NaNH2
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H2O, H2SO4
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HX
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SOCl2
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PBr3
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NaOH or KOH
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NaOR
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weak base, ethanol (or other polar protic solvent), heat
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acid (usually H2SO4 or H3PO4), heat
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small base
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large base
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Cl2, light
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Br2, light
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radical initiator, Br2 (e.g. NBS/heat or Br2/light)
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Br2, cold, dark, no peroxides
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radical initiator, HBr
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HBr, cold, dark, no peroxides
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Mg metal, diethyl ether
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2 Li metal, diethyl ether
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HOR or HOH
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1) Li or Mg metal, diethyl ether 2) D2O
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1) R3C-Z (Z = Li or MgX), diethyl ether 2) H3O+, H2O (dilute acid)
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1) R3C-Z (Z = Li or MgX), diethyl ether 2) R’’CH2X
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1) LiAlH4 or NaBH4 2) H3O+, H2O (dilute acid)
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1) Li metal 2) CuI
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any deuterated strong acid
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H2SO4, HNO3
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anhydrous sulfuric acid (H2SO4, no water)
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Br2, FeBr3 or Cl2, FeCl3
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RX, AlX3 (X = Cl or Br)
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XRC=O, AlX3 (X = Cl or Br)
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Zn(Hg), HCl
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H2, Pd
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H2O, H3O+
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HCN, CN-
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Nuc-, HNuc
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SOCl2 or PBr3
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R’NH2, H+
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R2’NH, H+
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1) R’OH, H+ 2) R’OH, H+
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H+
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1) NaH 2) R’X
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1) Nuc- (NOT grignards, lithium reagents, and RCC-) 2) H+
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H+, R2NH
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H2NNH2, KOH
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1) PPh3, butyllithium 2) R2CO
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1) LiAlH4 or NaBH4 2) H3O+
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1) LiAlH4 or NaBH4 2) H3O+
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1) LiAlH4 2) H3O+
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R’OH (excess), H+
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H2O (excess), H+
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1) KOH 2) H+
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H+ or R’’ONa
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H+ or 1) -OH 2) neutralize
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1) CO2 2) neutralize
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1) R’MgBr 2) H+, H2O
Note
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