Question

2. Explain why the following compound reacts to give a mixture of alkene stereoisomers in which only the cis-dimethyl isomer contains deuterium. Hint: draw the alkyl halide in a Newman projection. You will be asked to do this on midterm 1. Br CH,CH,OH Das * Change CACHON le CH3 C'H + CH3CH,0. H;c Stvong base

Please explain how to draw the newman projection as well.

Answer 1

Нас CH3 H3C CH3 trans alkene without D rotation of front carbon Dthrough sigma bond to H3C get D and Br antiperiplainer CH3 for elimination CH3 view H3C CH3 point OCH2CH3 rotation of front carbon through sigma bond to get H and Br antiperiplainer for elimination CH3 CH3 CH3 CH3 CH3 CH3 cis alkene with D OCH2CHa