Explain why the ether obtained by treating an optically active alcohol with PBr 3 followed by sodium

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Explain why the ether obtained by treating an optically active alcohol with PBr3 followed by sodium methoxide has the same configuration as the alcohol, whereas the ether obtained by treating the alcohol with tosyl chloride followed by sodium methoxide has a configuration opposite that of the alcohol.

CH3 CH3 1. PBr3/pyridine R OH R

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Organic Chemistry

ISBN: 978-0131407480

4th edition

Authors: Paula Yurkanis Bruice

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