Question

9 & 10. Treatment of the optically pure (S)- cyclohexanone (1) shown below with sodium methane thiolate in THF (tetrahydrofuran the solvent) gives products A and B that both have the same molecular formula CgH14SO. Compound A and B are easily physically separated by distillation with A having the lower boiling point and it is found that the optical rotation of the purified and separated substances A and B [ajo 0. It is experimentally found that the rate of formation of A and B are tripled when the concentration of sodium methane thiolate is tripled. Compounds A and B are then separately treated with ozone giving a single product C that is also optically inactive ([a]o 0). Answer the following questions pertaining to these transformations. Assume that the stereochemistry of the starting material 1 is only exactly as drawn below. A +B / NaSCH3 THF Br (S)-1 [alp 0 1. O3. CH3OH solvent) 2. S(CH3)2 PRODUCT 9. Using the structures of the possible products below, the product distribution can best be described as: I O SCH3 Iv o SCH SCH3 SCH3 a. b. c. d. e. consisting of I and an equal mixture of Ill and IV consisting of an equal mixture of IlI and IV consisting of Il and an equal mixture of III and IV consisting of an equal mixture of I and lI consisting of IV and an equal amount of I

Answer 1

CA Na s o lom An s: