Oxidation and Reduction Reagents

• Pd, Pt, or Ni + H2

  Alkene Hydrogenation, syn addition (yields alkane)
• Pd-C + 2 H2

  Alkyne Hydrogenation (yields Alkane)
• Pd on CaCO3 + Pb(OCOCH3)2 + quinoline (Lindar's Catalyst) + H2

  Alkyne Hydrogenation (yields Cis Alkene)
• Na + NH3

  Alkyne Hydrogenation (yields Trans Alkene)
• 1. LiAlH4

  2. H2O

  Reduction of alkyl halides (yields alkane)
• 1. LiAlH4

  2. H2O

  Reduction of Epoxides (yields alcohol)
• MCPBA or Peroxyacetic acid (RCO3H)

  Epoxidation of Alkenes (yields top or bottom epoxide and carboxylic acid)

  
• 1. RCO3H

  2. H2O (H+ or OH-)

  Alkene Dihydroxylation (trans diol)
• 1. KMnO4

  2. H2O, -OH

  
  

  OR

  
  

  1. OsO4

  2. NaHSO3, H2O

  Alkene Dihydroxylation (cis diol)
• 1. O3

  2. Zn, H2O or CH3SCH3

  Alkene Ozonolysis (oxidative cleavage) yields two carbonyls
• 1. O3

  2. H2O

  Internal Alkyne Ozonolysis (oxidative cleavage) yields two carboxylic acids
• 1. O3

  2. H2O

  Terminal Alkyne Ozonolysis (oxidative cleavage) yields a carboxylic acid and CO2
• 1. KMnO4

  2. -OH

  Internal Alkyne Ozonolysis (oxidative cleavage) yields a diketone
• PCC + CH2Cl2

  Oxidation of 1* alcohol (yields aldehyde)
• K2Cr2O7 +

  H2SO4, H2O

  Oxidation of 1* alcohol (yields carboxylic acid)
• K2Cr2O7 +

  H2SO4, H2O

  
  

  OR

  
  

  PCC + CH2Cl2

  Oxidation of 2* alcohol (yields ketone)
• Alkene Hydrogenation

  
• Alkyne Hydrogenation

  
• alkyne to cis alkene

  Lindlar's catalyst

  
• primary alcohol

  
• secondary alcohol