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.

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camache7429 camache7429

30-03-2020
Chemistry

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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.

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Q 7.34: At the end of a shift, the sales clerk turned over $21,476.38 in cash, checks, and credit card receipts to the cashier. When the supervisor looked at th

OrethaWilkison OrethaWilkison · Answer 1 · 2020-04-03T14:08:39+02:00

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.
[tex]C_{6}H_{5}S^{-}[/tex] gives [tex]S_{N}2[/tex] reaction with p-toluenesulfonate derivative to produce a thioether with (S) configuration. Here inversion of configuration takes place due to backside attack by [tex]C_{6}H_{5}S^{-}[/tex].
Structure of product has been shown below.

pstnonsonjoku pstnonsonjoku · Answer 2 · 2022-03-18T16:41:14+01:00

The reaction of p−toluenesulfonate and sodium benzenethiolate occurs by SN2 mechanism hence there is inversion of configuration and the chiral center.

In these series of reactions, p−toluenesulfonate is derived from (R)−2−octanol and p−toluenesulfonyl chloride. The product is shown in the images attached.

The reaction of p−toluenesulfonate and sodium benzenethiolate occurs by SN2 mechanism hence there is inversion of configuration and the chiral center as shown in the image attached.

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