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LAH or NaBH4
1. RMGBR or RLi 2. H2O, HCl
H2O
R''OH
ROH, HCl
RNH2, HCl
H2CrO4 or Ag2O, NaOH
RCO3H
LiAlH4
ROH, H+
SOCl2, base
ketoester
1. LiAlH4 2. H3O+
1. LAH 2. H3O+
1. NaBH4 2. H+
ROH
2NHR2
H2O
(R)2CuLi
H2O
ROH
2NHR2
LiAlH4
H+/H2O or NaOH
1. H+ 2. ROH
RMgBr or RLi
1. LiAlH4 2. H2O
HCl/H2O or NaOH/H2O and heat
1. LiAlH4 2. H2O
H2SO4/H2O or NaOH/H2O
Br2
Methyl-ester
1. Ketone 2. H+
Methyl-bromine
1. 3-butenone 2. H2O
+hydroxyketone
Br2
Methyl-bromine
1. 3-butenone 2. H2O