Question

Optically pure 2-octyl sulfonate, a compound with a leaving group comparable to the tosylate and mesylate groups discussed in this chapter, was treated with varying mixtures of dioxane and water as solvent. The optical purity of the resulting 2-octyl alcohol, a solvolysis product, varied with the ratio of dioxane to water according to the given table. Given that dioxane possesses fairly nucleophilic oxygen atoms (and, therefore, participates DIRECTLY in the mechanism of this reaction), provide a complete mechanism that explains the variation in the solvolysis product’s optical purity due to changes in solvent composition. 2-octyl sulfonate ---------------------------> OH-CH3-CH2CH2CH2CH2CH2CH3 dioxane Solvent Ratio Optical Purity of (water:Dioxane) 2-Octyl alcohol 25:75 77% 50:50 88% 75:25 95% 100:0 100%

Answer 1

This forum doesn't support drawing mechanisms.