Mechanisms&Conditions - DMF H2O if Nu:=strong acid...

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Mechanism LG Nu: Solvent Other Notes Good Bad Good Bad Good Bad SN1 WANT "weak" Nu: = solvent = base!!! Racemization H2O R-OH R-COOH SN2 TsO*, MsO* F* RO* H2O POLAR APROTIC PROTIC Tosylates CH3COO* *OH R-OH no OH, NH H2O Mesylates *OH NH2*, PH2* acetone ~ R-OH I*, Br*, Cl* RO* Ph-O* DMSO R-NH-R' diazonium salts (N2) HS* CH2COO*
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Unformatted text preview: DMF H2O if Nu:=strong acid RS* halogens I*>F* acetonitrile NH2* EtOH H* HMPA PROTIC Na+ *Br E1 SN1 b/c C* Saytzev/Hofmann E2 Nu:/Solvent => Eto* (strong base) BBB Antiperiplanar Organometallic diethyl ether R-MgX => strong base tetrahydrofuran sensitive to steric factors...
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This note was uploaded on 09/24/2009 for the course CHEM Chemistry taught by Professor Nitche during the Spring '08 term at Berkeley.

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