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Nucleophilic substitution

Organic Chapter 6 ppt

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Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination Organic Chemistry, 6h Edition L. G. Wade, Jr. Chapter 6 * Classes of Halides Alkyl: Halogen, X, is directly bonded to sp3 carbon. Most reactions result from breaking of this bond. C ? X bond is polar (EN difference) C is slightly positive ? electrophilic (can be attacked by nucleophile) X can leave with electrons ? elimination X can be replaced with another functional group ? substitution Chapter 6 Chapter 6 * Classes of Halides Examples: CHCl3 ? chloroform (solvent) CHClF2 ? freon-22 (refrigerant) CCl3 ? CH3 ? 1,1,1-trichloroethane (cleaning fluid) CF3 ? CHClBr ? halothane (nonflammable anesthetic) Chapter 6 Chapter 6 * Classes of Halides Vinyl: X is bonded to sp2 carbon of alkene. Examples:

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8.1 Functional Group Transformation by Nucleophilic Substitution Nucleophilic substitution reactions of alkyl halides are related to elimination reactions in that the halogen acts as a leaving group on carbon and is lost as an anion. The carbon-halogen bond of the alkyl halide is broken heterolytically: the two electrons in that bond are lost with the leaving group. The most frequently encountered nucleophiles are anions, which are used as their lithium, sodium, or potassium salts. If we use M to represent lithium, sodium, or potassium, some representative nucleophilic reagents are Table 8.1 illustrates an application of each of these to a functional group transformation. The
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