5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that explains the variation in in the product's optical purity due to changes in solvent composition. Hint, the solvent is doing more here than just dissolving. it is partaking in the reaction. Solvent Ratio (water : dioxane). 25:75 50: 50 75: 25 100:0 Optical purity of (S)-2-octanol. 77% 88% 95% 100% H20 OH (R)-2-0ctyl sulfonate (optically pure) (S)2-Octanol (dioane)

5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that explains the variation in in the product's optical purity due to changes in solvent composition. Hint, the solvent is doing more here than just dissolving. it is partaking in the reaction. Solvent Ratio (water : dioxane). 25:75 50: 50 75: 25 100:0 Optical purity of (S)-2-octanol. 77% 88% 95% 100% H20 OH (R)-2-0ctyl sulfonate (optically pure) (S)2-Octanol (dioane)

Macroscale and Microscale Organic Experiments

7th Edition

ISBN:9781305577190

Author:Kenneth L. Williamson, Katherine M. Masters

Publisher:Kenneth L. Williamson, Katherine M. Masters

Chapter43: Amines

Section: Chapter Questions

Problem 7Q

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