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What compound provides (S)-2-bromopentane upon exposure to TsCl then NaBr?Select answer from the options below(S)-2-pentanol2-pentene(R)-2-pentanol1-pentene

Question

What compound provides (S)-2-bromopentane upon exposure to TsCl then NaBr?Select answer from the options below(S)-2-pentanol2-pentene(R)-2-pentanol1-pentene

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Solution

The compound that provides (S)-2-bromopentane upon exposure to TsCl then NaBr is (S)-2-pentanol.

Here's the step-by-step process:

  1. (S)-2-pentanol is the starting material. The (S) indicates the stereochemistry of the alcohol.

  2. The alcohol is first treated with TsCl (tosyl chloride) in the presence of a base. This converts the alcohol into a tosylate, a good leaving group. The stereochemistry is preserved in this step.

  3. The tosylate is then treated with NaBr (sodium bromide). The bromide ion acts as a nucleophile and substitutes the tosylate, again preserving the stereochemistry.

  4. The final product is (S)-2-bromopentane.

This problem has been solved

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