Solutions_Manual_for_Organic_Chemistry_6th_Ed 112

Solutions_Manual_for_Organic_Chemistry_6th_Ed 112 - lEaviNg...

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6-22 slow planar carbocatioN .. - :Br: + ± CH3CH20H± Be (or simply Hr) 6±23 ThE structurE that caN forM thE morE stablE carbocation will undErgo S ² 1 fastEr. (a) 2³bromopropaNE´ will foRm a 2° carbocation µb) 2±bromo±2±mEt¶ylbUtanE´ will fo· a 3° carbocation ¸c) allyl bromIdE is fastEr t¶aN ¹ºpropyl brom»dE´ allyl broM»dE can foRm a rEsonaNcEºstab¼lizEd iNtE·EdiatE½ ¸d) 2-bromopropaNE´ will foRM a 2° carbocatioN (E) 2±¾odo±2¿mEt¶ylbutanE is fastEr thaN À±butyl chloÁidE (iod¾dE ¾s a bEttEr lEaving groUp t¶aN chloRidE) (F) 2±bromo±2-mEt¶YlbutanE (3°) is fastEr thaN Et¶yl iodidE (1°); althoUg¶ iodidE is a soMEw¶at bEttEr
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Unformatted text preview: lEaviNg group, thE diFfErEncE bEtwEEn 3 and 1 carbocatioN stabiLity doMiNatEs 624 oniZatioN is thE ratEdEtEiniNg stEp n S l. Anyting that stabilizEs thE intEEdiatE wil spEEd thE rEactio Both oF thEsE compounds For rEsoNacEstabilizEd intERMEdiatEs H ( H I H H H V H allylic bEnzylic + ( ) CH2 - O CHz < } H 625 H H I t + I CH T t HCH Br + CH C CHCH + H R-CHCH ( B r C H H cH3 CHCH3 f-- h3 Chch3 / I I .. (i. i :?: C 3 CHCH 9 : H + ? CH3 CHCH3 H ChCH 105...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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