sodium in ethanol Heating;

sodium hydroxide; sodium dithionite; oxygen 1) methanol, reflux, 10 min; Yield given. Multistep reaction;

1: 2.) 0.5 N NaOH, air-O2 / 1.) THF, -40 deg, 2.) CH2Cl2, 5 min 2: 2.) 1N NaOH, air-O2 / 1.) CH2Cl2, room temp., 16 h, 2.) CH3OH, 5 min 3: 1.) 0.5 N NaOH, Na2S2O3, 2.) air / 1.) 60 deg C, 1 h, 2.) 10 min View Scheme

sodium hydroxide; bromine 1) CCl4, room temperature, 2 h, irradiation, 2) ether, 2 min; Yield given. Multistep reaction. Yields of byproduct given;