Stereochemical isomers with hydroxy groups were synthesized by reacting 2-(
dimethoxymethyl)cyclohexanone with propargylmagnesium bromide. The stereo c
hemical structures were identified by NMR spectral interpretation and the g
eometry optimization. To assist the NMR interpretation, geometry optimizati
on based on semi-empirical AM1 and PM3 methods was applied. Throughout this
study, the structures of the two isomers were all determined and H-1 and C
-13 NMR spectra were fully assigned. It was proven that the less polar isom
er is an axial alcohol and the more polar one is an equatorial alcohol.