Birch reduction: partial reduction of benzene ring (dissolving metal) (Benzene + Na (or Li) in liquid NH3 with alcohol → 1,4-cyclohexadiene (not fully saturated)

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Benzene + Na (or Li) in liquid NH3 with alcohol → 1,4-cyclohexadiene (not fully saturated cyclohexane).

What each symbol means

SymbolWhat it stands for
EtOHProton source to protonate radical anions / dianions
NH3(l)Dissolving metal generates solvated electrons that reduce the ring

When to use this

Dissolving-metal reduction. Substituted benzenes: electron-donating groups direct reduction to different positions than electron-withdrawing groups (JEE compares outcomes qualitatively).