Question: Explain why the ether obtained by treating an optically active alcohol with PBry followed by sodium methoxide has the same configuration as the alcohiol, whereas
Explain why the ether obtained by treating an optically active alcohol with PBry followed by sodium methoxide has the same configuration as the alcohiol, whereas the ether obtained by treating the alcohol with tosyl chloride followed by sodium methoxide has a configuration opposite to that of the alcohol because conversion of the alcohol to the ether by way of an alky halide does not involve the breakage of asymmetric caibon bonds, whereas the same conversion by way of tosyl chloride involves the breakage of asymmetric carbon bonds because conversion of the alcohol to the ether by way of an alkyl halide requires fwo successive SN 2 reactions. ntireas the same coavergion by way of tosyl chloride tequires one SN2 reaction because conversion of the alcohol to the ether by way of an alkyl halide requirep one SN2 teacticn. wherees the same corversion by way of tosi diaide requires two fuccesive SN2 teactions because comversion of the alcohol to the ether by way of an akyl hallde involvos the breakage of asymmetric carbon bonds. Whereas the same converion by way of tosyl chloride does not involve the breakage of asymmetric carbon bonds
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