Mechanism Comparison - Substitution and Elimination...

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Substitution and Elimination Reactions Comparative Chart Reaction Structure of RX Reactivity of Nu: Conc. Of Nu: Solvent Stereochemistry SN2 1>2>3 Only this reaction and E2 will most likely react with a primary RX Strong nucleophile favors reaction High concentration of nucleophile favors reaction Aprotic polar solvent favors a SN2 reaction if eithe r of the reactants is charged ex: DMF DMSO Acetone inversion of configuration E2 3>2>1 Major product is more substituted alkene unless *the base is large *the alkyl halide is an alkyl flouride *the alkyl halide contains one or more double bonds Strong Base favors reaction High concentration of base favors reaction Aprotic polar solvent favors a E2 reaction if eithe r of the reactants is charged ex: DMF DMSO Acetone If the reactant has 2 H bonded to the carbon from which a H is to be removed, both E and Z result. The conformers that has the bulkiest groups on opposite sides will be the major product. Anti and syn elimination– if it
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This note was uploaded on 06/28/2010 for the course CHEM Chemistry taught by Professor Nitche during the Spring '08 term at University of California, Berkeley.

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