Octet / Reactions
Birch Reduction
Birch Reduction (Reduction.) Converts c1ccccc1 to C1=CCC=CC1 using Na or Li, NH₃(l), ROH. Conditions: -33°C (liquid ammonia).
Reduction
Reaction details
Name
Birch Reduction
Type
Reduction
Starting Material
c1ccccc1
Product
C1=CCC=CC1
Reagents
Na or Li
NH₃(l)
ROH
Conditions
-33°C (liquid ammonia)
Mechanism
- Smiles
c1ccccc1
- Description
Benzene
- Smiles
c1ccccc1
- Description
Single electron transfer from Na → radical anion
- Smiles
C1=CCC=CC1
- Description
1,4-Cyclohexadiene (unconjugated diene)
Tips
Aromatic → 1,4-Cyclohexadiene (partial reduction)
EDG (e.g., -OMe): double bonds remain ortho/para to group (meta positions reduced)
EWG (e.g., -COOH): group ends up on saturated carbon (ipso position reduced)
Different from catalytic hydrogenation (which gives cyclohexane)
Related Reactions
dissolving-metal-reduction
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