Question
Asked Dec 24, 2019
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Draw the products formed when (S)-butan-2-ol is treated with TsCl and pyridine, followed by NaOH. Label the stereogenic center in each compound as R or S. What is the stereochemical relationship between the starting alcohol and the nal product?

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Expert Answer

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Alcohols are converted into alkyl tosylates by treatment with para-toluenesulfonyl chloride (TsCl) in the presence of pyridine. The overall reaction converts - OH (a poor leaving group) into - OTS (a good leaving group). The stereochemistry of the reaction is retention of conf...

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