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lora16 [44]
4 years ago
6

The p−toluenesulfonate derived from (R)−2−octanol and p−toluenesulfonyl chloride was allowed to react with sodium benzenethiolat

e (C6H5SNa). Give the structure, including stereochemistry, of the product.

Chemistry
1 answer:
tangare [24]4 years ago
5 0

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.

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