For ten points, identify this reaction, which reduces a benzene ring to a 1,4-cyclohexadiene and which is named for an Australian chemist.
A naïve analysis of the mechanism of this reaction would lead one to the wrong product as the three mesomers of its dienyl carbanion intermediate must be considered. An optional step in this reaction occurs only if a component is conjugated with the involved arene, in which case alkene double bonds will be reduced. Substituents on the reactant can control this reaction's regioselectivity because electron-donating groups favor protonation at an unoccupied site meta- to the substituents, while electron-attracting substituents favor para-protonation. The conditions for this reaction usually feature an alkali metal dissolved in liquid ammonia, which can be understood as providing solvated protons and electrons. For ten points, identify this reaction, which reduces a benzene ring to a 1,4-cyclohexadiene and which is named for an Australian chemist.
A naïve analysis of the mechanism of this reaction would lead one to the wrong product as the three mesomers of its dienyl carbanion intermediate must be considered.
the {Birch} reduction