SCAN0005 - 9 MM 8W A YW‘J’ Bio> Wk\H Example 3 64 33...

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Unformatted text preview: 9/\ MM\ 8W @ A, YW‘J’ Bio >(\ Wk \H\ Example 3% 64% 33% i l / Intermediate: carbocation p?” Q“ + 86W This carbocation can: a) carbocation can lose a proton as shown W“ 3% positively charged carbon z“. [”3” 97% C _ _.> tertiary carbécation; more stable Another rearran ement Rearran ement involves h dride shifl ( g g y M WOH H3P04 _—.’ \/\ + H3CHC—CHCH3 A heat mixture of cis (32%) R a ‘ ~ 12% and trans-2 -butene (56%) \ us BQ‘VCU’VB a) oxonium ion can lose water and a proton (from C-2) to give l-butene; doesn‘t give a carbocation directly because primary carbocations are too unstable H Vii/13%” a \J 0H\ \/\ b) hydrogen migrates with its pair of electrons from C-2 to C-1 as water is lost; carbocation formed by hydride shift is secondary + H20 + H+ ...
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