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(R)-2-Bromooctane reacts with NaSH to fo...

(R)-2-Bromooctane reacts with NaSH to form (S)-2-octanethiol with inversion of configuration at the stereocentre. How cann we obtain (R)-2-octanethiol from (R)-2-bromoctane?

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We know that `S_(N)2` reactions proceeds with inversion of configuration at the stereocentre. If however, two `S_(N)2` reactions are carried out at the same stereocentre of a compound, retention of configuration will occur. Thus, (R)-2-octanethiol can be obtained from (R)-2-bromooctane by first reacting it with NaI in acetone and then with NaSH in ethanol.
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