10-19 - 1 Nucleophilic Substitution Reactions 106 Continued...

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Unformatted text preview: 1 Nucleophilic Substitution Reactions 106 Continued Reaction Complexity Product Mixtures substitution elimination 107 Reaction Mechanisms - Kinetics H E1 = Elimination 1st Order Br + OEt rate = k 108 H H H H Br E1 Br OEt E t O H Br Carbocation Stabilization Recall: Alkyl groups stabilize carbocations hyperconjugation a partial Ⱥ bond 109 = a partial Ⱥ-bond LUMO HOMO Elimination: E1 C C H Br ¡ C C H 110 C C H ¡ H C C H H H B: Elimination: E1 Ʃ G ‡ 111 E R 2 Elimination: E1 Which is the A. 1-alkene 112 major product? B. 2-alkene Elimination: E1 Ʃ G ‡ 113 E R major product Reactions of Carbocations react with nucleophiles 114 Reactions of Carbocations react with nucleophiles 115 eliminate H ¡ Reactions of Carbocations react with nucleophiles 116 eliminate H ¡ C C R rearrange C C R C C Reaction Mixtures substitution elimination Does increasing the basicity of the nucleophile 118 Does increasing the basicity of the nucleophile increase the rate of E1 reaction? a. Yes b. No 2 Elimination: E1 Which is the A. 1-alkene 112 major product? B. 2-alkene Elimination: E1 Ʃ G ‡ 113 E R major product Reactions of Carbocations react with nucleophiles 114 Reactions of Carbocations react with nucleophiles...
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This note was uploaded on 12/25/2009 for the course CHE 320 taught by Professor Ff during the Spring '09 term at SUNY Stony Brook.

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10-19 - 1 Nucleophilic Substitution Reactions 106 Continued...

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