有機化學第11ç« ï&f

有機化學第11ç« ï&f

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Unformatted text preview: 1 11. Reactions of Alkyl Halides: Nucleophilic Substitutions 親核取代 and Eliminations 脫離 Based on McMurry’s Organic Chemistry , 7 th edition Alkyl Halides React with Nucleophiles and Bases 取代 脫離 2 2 Why this Chapter? Nucleophilic substitution, base induced elimination are among most widely occurring and versatile reaction types in organic chemistry Reactions will be examined closely to see:- How they occur- What their characteristics are How they can be used 3- How they can be used OUTLINE ¡ The Discovery of Nucleophilic Substitution Reactions Nucleophilic Substitution Reactions ¡ The S N 2 Reaction ¡ Characteristics of the S N 2 Reaction ¡ The S N 1 Reaction ¡ Characteristics of the S N 1 Reaction 4 3 OUTLINE ¡ Biological Substitution Reactions ¡ Elimination of Alkyl Halides: Zaitsev’s Rule ¡ The E2 Reaction and the Deuterium Isotope Effect ¡ The E2 Reaction and Cyclohexane Conformation ¡ The E1 and E1cB Reaction ¡ Biological Elimination Reactions ¡ Summary of Reactivity: S 1 S 2 E1 E1cB E2 5 ¡ Summary of Reactivity: S N 1, S N 2, E1, E1cB, E2 11.1 The Discovery of Nucleophilic Substitution Reactions In 1896 Paul Walden 蘋果酸 6 The reactions involve substitution at that center Therefore, nucleophilic substitution can invert the configuration at a chirality center 4 Stereochemistry of Nucleophilic Substitution 7 (Kenyon and Phillips, 1929) 8 5 Nucleophilic Substitution Reaction Primary and secondary alkyl halides and tosylates always proceed with inversion of configuration 9 ROTos Alky toluene sulfonate (Tosylate) W.E 11.1 10 6 W.E 11.1 11 P. 11.1 12 7 P. 11.1 13 11.2 The S N 2 Reaction Kinetics 14 8 The S N 2 Reaction ¡ Hughes and Ingold nomenclature to describe characteristic step: ¡ S=substitution ¡ N (subscript) = nucleophilic ¡ 2 = both nucleophile and substrate in characteristic step (bimolecular) 15 S N 2 Process The reaction involves a transition state in which both reactants are together 16 9 17 S N 2 Transition State The transition state of an S N 2 reaction has a planar arrangement of the carbon atom and the remaining three groups and the remaining three groups 18 10 P. 11.2 19 P. 11.2 20 11 P. 11.3 21 P. 11.3 22 12...
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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有機化學第11ç« ï&f

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