Birch Reduction: Aromatic Rings → 1,4‑Cyclohexadienes (Regioselectivity Rules)

Learn the Birch reduction: solvated electrons, radical anions, protonations, and how EDG vs EWG substituents control where the double bonds end up.

Reaction: Arene → 1,4-cyclohexadiene
What it does: Partially reduces aromatic rings
Typical reagents: Na or Li in liquid NH3, alcohol (proton source)
Key intermediate: Radical anion; cyclohexadienyl anion
Driving force: Stepwise e−/H+ additions
Exam type: Reductions
Exam type: Regiochemistry

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