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Solutions_Manual_for_Organic_Chemistry_6th_Ed 197

Solutions_Manual_for_Organic_Chemistry_6th_Ed 197 - 8-72...

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8-72 First, we explain how the mixture of stereoisomers results, then why. We have seen many times that the bridged halonium ion permits attack of the nucIeophile only from the opposite side. expected: Q Ci-CI --- H Ph W CI� �:S:1: H Ph ~ H Cl trans only A mixture of cis and trans could result only if attack of chloride were possible from both top and hottom, something possible only if a carbocation existed at this carbon. actual: '" 0� H Ph H --� H CI trans +� H Ph cis This picture of the p orbitals of benzene show
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