Ch_322a_6.01

Ch_322a_6.01 - Chapter 6 Ionic Reactions: Nucleophilic...

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Chapter 6 Ionic Reactions: Nucleophilic Substitution and Elimination Reactions of Alkyl Halides Alkyl Halides: R-X The carbon center is sp 3 hybridized in alkyl halides and the C-X bond is polarized as shown because of the greater electronegativity of the halogen. C X ! + !" As the halogen atom in R-X changes from F to I, the C-X bond length increases, and the C-X bond strengths decreases . H 3 C-F H 3 C-Cl H 3 C-Br H 3 C-I bond length (A) o 1.39 1.78 1.93 2.14 bond strength 112 83.8 70.1 57.2 (kcal/mol) The relative reactivities of the alkyl halides (R-I>. ..... >R-F) is explained by the large differences in R-X bond strengths.
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Vinylic and Phenyl Halides In these compounds, the carbon is sp 2 hybridized which results in a stronger C-X bond. The nucleophilic substitution reactions discussed in this chapter do not occur with these types of halides. C=C X a vinylic halide C=C Cl H H H "vinyl chloride" (chloroethene) CH 2 =CH- the vinyl group X a phenyl halide Br bromobenzene the phenyl group
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_6.01 - Chapter 6 Ionic Reactions: Nucleophilic...

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