The Birch reduction of methoxybenzene (anisole) using sodium metal in liquid ammonia and ethanol pro — Aromatic Hydrocarbons Chemistry Question

💡 Solution & Explanation

In the Birch reduction of aromatic rings possessing an electron-donating group (EDG) like $-OCH_3$, the regiochemistry is governed by the maximization of stabilization for the radical anion intermediates. This leads to the diene forming such that the EDG is placed on one of the $sp^2$ hybridized carbons of the resulting double bonds, yielding 1-methoxy-1,4-cyclohexadiene.