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10-19 - Product Mixtures Nucleophilic Substitution...

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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 Br E1 Br OEt E t O H Br Carbocation Stabilization Recall: Alkyl groups stabilize carbocations hyperconjugation a partial Ⱥ bond 109 = -bond LUMO HOMO Elimination: E1 C C H Br H 110 H H H H B: Elimination: E1 Ʃ G 111 E R
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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 increase the rate of E1 reaction? a. Yes b. No
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3 Reaction Mechanisms - Kinetics E2 = Elimination 2nd Order Br EtO rate = k 119 E2 + H EtO E2 Mechanism The E2 elimination is concerted : Bond breaking occurs at the same time as 120 bond formation E2 EtO C C H Br H 121 H B \ : concerted reaction
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