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Preparation and Structure of Sodium Methoxide

        Sodium methoxide is prepared by carefully treating methanol with sodium:

2 Na + 2 CH3OH → 2 CH3ONa + H2

        The reaction is so exothermic that ignition is possible. The resulting solution, which is colorless, is often used as a source of sodium methoxide, but the pure material can be isolated by evaporation followed by heating to remove residual methanol. The solid hydrolyzes in water to give sodium hydroxide, and commercial samples can be contaminated with the hydroxide. The solid and especially solutions absorb carbon dioxide from the air, thus diminishing the effectiveness of the base.
        In the solid form, sodium methoxide powder is polymeric, with a sheet-like arrays of Na+ centers, each bonded to four oxygen centers.
        The structure, and hence its basicity, of sodium methoxide in solution depends on the solvent. It is significantly stronger base in DMSO where it is more fully ionized and free of hydrogen bonding.