Lect20_1007 - 9. The Reaction of tert-Butyl Chloride with...

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Ch. 6 - 1 3 3 3 2 3 3 3 9. The Reaction of tert-Butyl Chloride with Hydroxide Ion: An S N 1 Reaction Multistep Reactions & the Rate Multistep Reactions & the Rate - - Determining Step Determining Step
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Ch. 6 - 2 Free Energy Diagram of S Free Energy Diagram of S N 1 Reactions 1 Reactions T.S. (1) (CH 3 ) 3 C-OH +Br - T.S. (2) T.S. (3) (CH 3 ) 3 C-OH 2 - (CH 3 ) 3 C - (CH 3 ) 3 CBr +H 2 O G 1 intermediate
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Ch. 6 - 3 2 intermediates and 3 transition states (T.S.) The most important T.S. for S N 1 reactions is T.S. (1) of the rate- determining step (r.d.s.)
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Ch. 6 - 4 11A. 11A. The Structure of The Structure of Carbocations Carbocations 11. Carbocations C H 3 C H 3 C CH 3
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Ch. 6 - 5 Stability of cations most stable (positive inductive effect) Resonance stabilization of allylic and benzylic cations 2 2
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11B. 11B. Hyperconjugation Hyperconjugation 11. Carbocations
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Ch. 6 - 7 Ph Br CH 2 CH 3 CH 3 CH 3 OH ( ) CH 3 OH attack from right CH 3 OH Ph C CH 3 OCH 3 CH 2 CH 3 ( )and( ) racemic mixture 50:50 chance 12. The Stereochemistry of S N 1 Reactions Ph CH 3 O CH 2 CH 3 CH 3 ( ) Ph OCH 3 CH 2 CH 3 CH 3 ( ) (1 : 1)
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Ch. 6 - 8
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This note was uploaded on 02/20/2012 for the course CHEM 333 taught by Professor Lavigne during the Fall '09 term at South Carolina.

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Lect20_1007 - 9. The Reaction of tert-Butyl Chloride with...

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