Interactions | Reactions | Processes

Classified as: Birch Reduction

Birch reduction involves an SET from the metal to the pi-system to give the radical anion. This species abstracts a proton from the solvent forming a radical. A second SET occurs giving the anion. This abstracts another proton from the solvent. Subtle changes in product can be obtained by controlling solvent pKa.

For more information look in the Chemogenesis webbook sections on redox chemistry and substitution, transfer, abstraction, displacement (STAD).
  +  
2
Na
  +  
Hg
  +  
2
CH3CH2OH
         
  +  
2
Na+
  +  
2
CH3CH2O–

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  +  
2
Na
  +  
  +  
4
[H]
         
  +  
2
Na+

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  +  
4
Na
  +  
4
CH3CH2OH
  +  
NH3
         
  +  
4
Na+
  +  
4
CH3CH2O–

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  +  
8
Li
  +  
CH3CH2NH2
  +  
8
[H]
         
  +  
8
Li+

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  +  
2
Li
  +  
2
CH3CH2NH2
         
  +  
2
Li+
  +  
2

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  +  
2
Li
  +  
CH3CH2NH2
  +  
2
[H]
  +  
H2O
          
  +  
CH3OH
  +  
2
Li+

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  +  
2
Li
  +  
2
CH3CH2NH2
         
  +  
2
Li+
  +  
2

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  +  
2
Li
  +  
CH3CH2NH2
  +  
2
[H]
  +  
H2O
          
  +  
(CH3)2NH
  +  
2
Li+

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© Mark R. Leach 1999 –

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please contact Mark R. Leach, the author, using mark@meta-synthesis.com