(Solved): Sodium cyanide reacts with 2-bromobutane in dimethylsulfoxide to form a substitution product. Draw ...

Sodium cyanide reacts with 2-bromobutane in dimethylsulfoxide to form a substitution product. Draw the substitution product formed when this enantiomer reacts with $$\mathrm{NaCN}$$ in DMSO. Clearly indicate stereochemistry by drawing a wedged bond, a dashed bond, and two in-plane bonds per each chiral carbon. Then identify the configuration of the starting material and the product. Draw curved arrows to show the movement of electrons that illustrates the mechanism of the reaction. For the $${\mathrm{S}}_{\mathrm{N}}2$$ reaction, draw the major organic product and select the correct $$(R)$$ or $$(S)$$ designation around the stereocenter carbon in the organic substrate and organic product. Include wedge-and-dash bonds and draw hydrogen on a stereocenter.