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Dolbier HW Solutions 562 - 23.2 b The negatively charged...

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CHAPTER 23 ARYL HALIDES SOLUTIONS TO TEXT PROBLEMS 23.1 There are four isomers of C 7 H 7 Cl that contain a benzene ring, namely, o , m , and p -chlorotoluene and benzyl chloride. Of this group only benzyl chloride is not an aryl halide; its halogen is not attached to the aromatic ring but to an sp 3 -hybridized carbon. Benzyl chloride has the weakest carbon–halogen bond, its measured carbon–chlorine bond dissociation energy being only 293 kJ/mol (70 kcal/mol). Homolytic cleavage of this bond produces a resonance-stabilized benzyl radical.
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Unformatted text preview: 23.2 ( b ) The negatively charged sulfur in is a good nucleophile, which displaces chloride from 1-chloro-2,4-dinitrobenzene. Cl NO 2 NO 2 1-Chloro-2,4-dinitrobenzene SCH 2 C 6 H 5 NO 2 Cl 2 1 NO 2 Benzyl 2,4-dinitrophenyl sulfide C 6 H 5 CH 2 S Na 1 2 C 6 H 5 CH 2 S 2 Na 1 Benzyl chloride Benzyl radical CH 2 1 Chlorine atom Cl CH 2 Cl Cl CH 3 p-Chlorotoluene CH 2 Cl Benzyl chloride Cl CH 3 m-Chlorotoluene CH 3 Cl o-Chlorotoluene 656...
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