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Topic+6+Notes+_substitutions_ (dragged) - Substrate:...

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S N 2 One-step (concerted) mechanism Substrate: Methyl>1°>2°>>3° - Steric bulk hinders attack of Nu Rate = k [substrate] [nucleophile] Chirality - Inversion Often performed in polar aprotic solvents, e.g. , DMF (Me 2 NCHO), DMSO (Me 2 SO) to dissolve substrate and ionic reagent, and increase reaction rate S N 1 Dissociation-Nucleohipic addition-Deprotonation
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Unformatted text preview: Substrate: 3>2>>1or methyl - Stability of carbocation intermediate Rate = k [substrate] - independent of [nucleophile] - rate depends on solvent polarity Chirality - racemization Generally only useful for solvolyses (reactions with H 2 O, ROH, RCO 2 H) SUMMARY: FACTORS EFFECTING S N 1 AND S N 2 REACTIONS Prob: 6.18,26 S:6.15;...
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This note was uploaded on 10/24/2010 for the course CHEM 2311 taught by Professor Tyson during the Spring '07 term at Georgia Institute of Technology.

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