Question

The p−toluenesulfonate derived from (R)−2−octanol and p−toluenesulfonyl chloride was allowed to react with sodium benzenethiolate (C6H5SNa). Give the structure, including stereochemistry, of the product.

Answer 1

Answer:

A thioether is formed as product with opposite configuration.

Explanation:

• (R)-2-octanol substitutes Cl from p-toluenesulfonyl chloride to produce p-toluenesulfonate derivative. Here stereochemistry of 2-octanol is retained as no bond breaking or bond formation takes place at chiral center.
• $C_{6}H_{5}S^{-}$ gives $S_{N}2$ reaction with p-toluenesulfonate derivative to produce a thioether with (S) configuration. Here inversion of configuration takes place due to backside attack by $C_{6}H_{5}S^{-}$.
• Structure of product has been shown below.