1: thionyl chloride 2: H2O View Scheme

in water Yield given;

hydrogenchloride; N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) cyclohexane-THF, -78 deg C, 0.5 h, 2.) 10 min, 3.) cyclohexane-THF-H2O, reflux, 14 h; Yield given. Multistep reaction. Yields of byproduct given;

hydrogenchloride; N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) cyclohexane-THF, -78 deg C, 0.5 h, 2.) 10 min, 3.) cyclohexane-THF-H2O, reflux, 14 h; Yield given. Multistep reaction. Yields of byproduct given;

hydrogenchloride; N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) cyclohexane-THF, -78 deg C, 0.5 h, 2.) 10 min, 3.) cyclohexane-THF-H2O, reflux, 14 h; Yield given. Multistep reaction. Yields of byproduct given;