Dolbier HW Solutions 563

Dolbier HW Solutions 563 - 23.5 Nucleophilic addition...

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ARYL HALIDES 657 ( c ) The nitrogen in ammonia has an unshared electron pair and is nucleophilic; it displaces chloride from 1-chloro-2,4-dinitrobenzene. ( d ) As with ammonia, methylamine is nucleophilic and displaces chloride. 23.3 The most stable resonance structure for the cyclohexadienyl anion formed by reaction of methox- ide ion with o - f uoronitrobenzene involves the nitro group and has the negative charge on oxygen. 23.4 The positions that are activated toward nucleophilic attack are those that are ortho and para to the nitro group. Among the carbons that bear a bromine leaving group in 1,2,3-tribromo-5-nitrobenzene, only C-2 satis F es this requirement.
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Unformatted text preview: 23.5 Nucleophilic addition occurs in the rate-determining step at one of the six equivalent carbons of hexa f uorobenzene to give the cyclohexadienyl anion intermediate. 1 Hexafluorobenzene F F F F F F Methoxide ion OCH 3 2 Cyclohexadienyl anion intermediate F F F F F F OCH 3 2 1,2,3-Tribromo-5-nitrobenzene Br Br Br NO 2 1,3-Dibromo-2-ethoxy-5-nitrobenzene OCH 2 CH 3 Br Br NO 2 NaOCH 2 CH 3 CH 3 O F N 1 O 2 2 O Cl NO 2 NO 2 1-Chloro-2,4-dinitrobenzene NHCH 3 NO 2 NO 2 N-Methyl-2,4-dinitroaniline CH 3 NH 2 Cl NO 2 NO 2 1-Chloro-2,4-dinitrobenzene NH 2 NO 2 NO 2 2,4-Dinitroaniline NH 3...
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