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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
