Lecture22final(10)

Lecture22final(10) - Organic Chemistry, Third Edition...

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1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 8 Alkyl Halides and Elimination Reactions
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2 Which is the major product of the following E2 reaction? CH 3 CHCH 2 CH 3 Br + HO ! CH CH 2 CH 3 CH 2 A. CH 3 H 3 C H H B. C CH 2 H 3 C H 3 C C. H H 3 C H CH 3 CH 3 CH 2 CH 2 CH 3 D. E. DMSO !
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3 I How many different alkene products are possible when the following alkyl halide undergoes E2 elimination? A. 1 B. 2 C. 3 D. 4 E. 5 !
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4 What is (are) the product(s) of the following reaction? DMSO !
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5
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6 What is (are) the product(s) of the following E2 reaction? I. A II. B III. C IV. D V. E CH 3 C CH 3 CH 2 Br CH 2 CH 3 !
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7 What is (are) the starting material(s) in the reaction below? !
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8 E1 Mechanism
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9 E2 Mechanism
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10 rate = k [(CH 3 ) 3 CCI] E1 Mechanism In an E2 reaction, the leaving group comes off as the ! proton is removed, and the reaction occurs in one step. However, in an E1, the leaving group comes off before the ! proton is removed, and the reaction occurs in two steps.
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11 Figure 8.6 Energy Diagram for an E1 Reaction
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12 The rate of an E1 reaction increases as the number of R groups on the carbon with the leaving group increases. Effect of Alkyl Halide Structure on E1 Reactions
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Effect of Base on the E1 Reaction The strength of the base usually determines if a reaction follows the E1 or E2 mechanism. Strong bases like ! OH and ! OR favor E2 reactions. Weaker bases like H
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This note was uploaded on 01/03/2012 for the course CHEM 233 taught by Professor Anamoore during the Fall '10 term at ASU.

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Lecture22final(10) - Organic Chemistry, Third Edition...

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