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Chlorination and bromination of aromatic compounds follow an electrophilic aromatc substitution mechanistic pathway resulting in substituted chlorinated and brominated aromatic rings. The following is an example of an aromatic electrophilic aromatic halogenation reaction: + Br2 CI- + -NEN: I, F, or CN can not be added to the aromatic ring using iron(III) halide as a Lewis acid. For example, due to thermodynamic reasons, the following reaction will not occur: + 1₂ FeBr₁ + KI Br Fel, However, iodobenzene can be prepared via the following reaction between a diazonium salt and potassium iodide: + HBr + HI + N₂ + KCI Nearly six decades ago, researchers suggested a free radical mechanism for this reaction. Suggest a one-step bimolecular mechanism that could be used to rationalize the formation of iodobenzene from the diazonium salt and potassium iodide

Chlorination and bromination of aromatic compounds follow an electrophilic aromatc substitution mechanistic pathway resulting in substituted chlorinated and brominated aromatic rings. The following is an example of an aromatic electrophilic aromatic halogenation reaction: + Br2 CI- + -NEN: I, F, or CN can not be added to the aromatic ring using iron(III) halide as a Lewis acid. For example, due to thermodynamic reasons, the following reaction will not occur: + 1₂ FeBr₁ + KI Br Fel, However, iodobenzene can be prepared via the following reaction between a diazonium salt and potassium iodide: + HBr + HI + N₂ + KCI Nearly six decades ago, researchers suggested a free radical mechanism for this reaction. Suggest a one-step bimolecular mechanism that could be used to rationalize the formation of iodobenzene from the diazonium salt and potassium iodide

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Question 4 Chlorination and bromination of aromatic compounds follow an electrophilic aromatc substitution mechanistic pathway resulting in substituted chlorinated and brominated aromatic rings. The following is an example of an aromatic electrophilic aromatic halogenation reaction: + Br₂ CI- * -NEN: I, F, or CN can not be added to the aromatic ring using iron(III) halide as a Lewis acid. For example, due to thermodynamic reasons, the following reaction will not occur: + 1₂ FeBr + ΚΙ Br Fel, However, iodobenzene can be prepared via the following reaction between a diazonium salt and potassium iodide: + HBr + HI + N₂ + KCI Nearly six decades ago, researchers suggested a free radical mechanism for this reaction. Suggest a one-step bimolecular mechanism that could be used to rationalize the formation of iodobenzene from the diazonium salt and potassium iodide
Transcribed Image Text:Question 4 Chlorination and bromination of aromatic compounds follow an electrophilic aromatc substitution mechanistic pathway resulting in substituted chlorinated and brominated aromatic rings. The following is an example of an aromatic electrophilic aromatic halogenation reaction: + Br₂ CI- * -NEN: I, F, or CN can not be added to the aromatic ring using iron(III) halide as a Lewis acid. For example, due to thermodynamic reasons, the following reaction will not occur: + 1₂ FeBr + ΚΙ Br Fel, However, iodobenzene can be prepared via the following reaction between a diazonium salt and potassium iodide: + HBr + HI + N₂ + KCI Nearly six decades ago, researchers suggested a free radical mechanism for this reaction. Suggest a one-step bimolecular mechanism that could be used to rationalize the formation of iodobenzene from the diazonium salt and potassium iodide
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