Answer to Question #257753 in Organic Chemistry for Koki

Question

Extra Credit (5 pts) Reaction in refluxing acetone of the nucleophile potassium phenoxide (Pho-K', drawn below) with the (S) enantiomer of the starting X-substituted epoxides below gives different enantiomeric epoxide products as a function of the leaving group X. Note also that compound 2 also reacts about 4x as fast as 1, suggesting that at least in acetone, the CH SO, Ion is a better leaving group than the CF ion. Consistent with this idea, CH SO OH is a stronger acid than HCl in organic solvents like acetone (but not in water). Write careful mechanisms to explain the differing stereochemical results

Answer 1

The solution diagram is as shown below: