CH3CH2SCH2CH3 can be synthesized by an Sn2 reaction. Draw the structures of the alkyl chloride and nucleophile that will give this compound in highest yield. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include all valence lone pairs in your answer. • Separate multiple reactants using the + sign from the drop-down menu. • When a metal counterion is needed, use Na+, but draw it in its own sketcher. Visited

Following are two diastereomers of 3-bromo-3,4-dimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3,4-dimethyl-3-hexene as the major product. One diastereomer gives the Ealkene, and the other gives the Z alkene. Which diastereomer gives the E alkene? Me Me H Me CO Following are two diastereomers of 3-bromo-2,3,4-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 2,3,4-trimethyl-3-hexene as the major product. One diastereomer gives the Ealkene, and the other gives the Zalkene. Which diastereomer gives the Z alkene? H Me Et Me Men Br Me Br Visited ΕΙ iPr iPr Co Following are two diastereorners of 3-bromo-4-ethyl-2,3,5-trimethylhexane. On treatment with sodium ethoxide in ethanol, each gives 3-ethyl-2,4,5-trimethyl-3-hexene as the major product. One diastereomer gives the Ealkene, and the other gives the Z alkene. Which diastereomer gives the E alkene? Et Me Br Br Me iPre EN H iPr iPr iPr biri