IMG_0005_NEW_0001 - BUT if base and leaving group are...

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1. o ruPon -r-\-r,^'-1 --------------- -OH DMSO or hexane or diethyl ether I @ NfoH- ,"^'-.,^'-- DMSO or hexane or diethyl ether ! (cH3)3cf,yo -'^\-,t\ DMSO or hexane ,.\V't- or diethyl ether I -'.* I section 8.5 to 8.10; 9.3 to 9.8 NOTE: for the above reactions you must consider other nucleophileslbases as well ALSO; El/S N1 reactions proceed via cation so you must consider 1 ,2-hydride shiffs 1,2-methylshifts or 1,2-alkyl shifts where such rearangements would provide a more stable cation (3o>P>1o) Sp2 - proceeds with inversion (notice non bulky nucleophile, aprotic solvent) DMSO = dimethyl sulphoxide - a polar APROTIC solvent OH -'-.-,,\ 2. section 8.2 to 8.4,8.7 to 8.10
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Unformatted text preview: BUT: if base and leaving group are protonwill occur (see below) Oe) (cH:):co Na DMSO or hexane or diethyl ether section 9.1, 9.2, 9.4-9.8 OH E2 - notice strong and BULKY base and aprotic solvent ALSO reaction will favor formation of more substituted alkene and E-alkene (consider Newman projection and removal of proton antito leaving group) hindered removal of least hindered-Y= I Hzo : 3. .,.^\--\ ---==> SN1 ! (cHe)3coH : ______----------,.-\. .'\ heat E1 Spl - proceeds with racemization (notice protic solvent, poor nucleophile) OH-,'^\.4^\ E1 - favors more substituted alkene- and E alkene - bulky, weak base I...
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