reduction

The Birch reduction is an organic reaction that is used to convert arenes to 1,4-Cyclohexadiene. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally liquid ammonia) with an alkali metal (traditionally sodium) and a proton source (traditionally an *******). Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane.

An example is the reduction of naphthalene in ammonia and ethanol:

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