1: 72 percent / sodium ethoxide / diethyl ether / 18 h / Ambient temperature 2: 1.) sodium ethoxide, 2.) water / 1.) ethanol, 5 min View Scheme

water; sodium ethanolate 1.) ethanol, 5 min; Yield given. Multistep reaction;

1: 1.) silver nitrate / 1.) water, 15 min, 2.) ether, reflux, 3 h 2: 1.) hydrogen bromide, 2.) sodium carbonate / 1.) toluene, 8 h, 2.) water, acetone, 50 deg C, 3.5 h 3: 1.) sodium ethoxide, 2.) water / 1.) ethanol, 5 min View Scheme

1: 1.) hydrogen bromide, 2.) sodium carbonate / 1.) toluene, 8 h, 2.) water, acetone, 50 deg C, 3.5 h 2: 1.) sodium ethoxide, 2.) water / 1.) ethanol, 5 min View Scheme

water; sodium ethanolate 1.) ethanol, 5 min; Yield given. Multistep reaction. Yields of byproduct given;