Lecture20CHM233(10)final

Lecture20CHM233(10)final - 1 Organic Chemistry, Third...

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Unformatted text preview: 1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawaii Chapter 7 Alkyl Halides and Nucleophilic Substitution 2 Characteristics of the S N 2 Mechanism 3 Which of the following S N 2 reactions is the fastest? CH 3 CH 2 CH 2 CH 2 Br + H 2 O CH 3 CH 2 CH 2 CH 2 OH + HBr CH 3 CH 2 CHBrCH 3 + H 2 O CH 3 CH 2 CHOHCH 3 + HBr CH 3 CH 2 CH 2 CH 2 Br + OH CH 3 CH 2 CH 2 CH 2 OH + HBr CH 3 CH 2 CHBrCH 3 + OH CH 3 CH 2 CHOHCH 3 + HBr CH 3 CH 2 CHClCH 3 + OH CH 3 CH 2 CHOHCH 3 + HCl A. B. C. D. E. ! 4 Which of the following species is the least nucleophilic? A. CN B. (CH 3 ) 3 N C. (CH 3 ) 3 CO D. H 2 O E. BF 3 ! 5 Which of the following species is the best leaving group? A. OH B. Cl C. Br D. F E. I ! 6 Which of the following compounds reacts most rapidly via an S N 2 mechanism? Cl Cl Cl Cl Cl E- A- B- C- D- ! 7 What is the product of the S N 2 reaction between ( R )-2-chloropentane and the hydroxyde ion? A- ( R )-2-pentanol B- ( S )-2-pentanol C- Racemic pentanol D- 1-Pentanol E- 3-Pentanol ! 8 Figure 7.13 The S N 2 Reaction in the Synthesis of Two Drugs 9 Nucleophilic substitution reactions are important in biological systems as well. This reaction is called methylation because a CH 3 group is transferred from one compound (SAM) to another (:Nu ! ). Nucleophilic Substitution Reactions in Biological Systems 10 Figure 7.14 Adrenaline synthesis from noradrenaline in response to stress S N 2 Reaction in Adrenaline Synthesis (CH 3 ) 2 SH + pKa = 5.4 11 Key features of the S N 1 mechanism are that it has two steps, and carbocations are formed as reactive intermediates. S N 1 Reaction Mechanism 12 Figure 7.15 Energy Diagrams for S N 1 Reactions 13 Stereochemistry of S N 1 Reactions 14 Loss of the leaving group in Step [1] generates a planar carbocation that is achiral ....
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Lecture20CHM233(10)final - 1 Organic Chemistry, Third...

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