Reactivity of substituted benzenes 1.0.1

2,4,6-tribromoanisole. 87 o-bromoaniline. 32 p-bromoaniline. 66. 2,4-dibromoaniline. 80. 2,6-dibromoaniline. 87. 2,4,6-tribromoaniline. 3 pages
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The Reactivity of Substituted BenzenesObjectiveTo investigate the reactivity of substituted benzenes and to examine the relationshipbetween electron withdrawing/donating groups and reactivityBackgroundBecause aromaticity is a stabilizing influence, benzene rings do not undergo electrophilicadditions as typical alkenes or non-aromatic conjugated π systems do. Instead, benzenerings undergo substitution reactions referred to as electrophilic aromatic substitution (eq.1). Additionally, the low reactivity of benzene rings requires that the electrophile beextremely reactive. For example, Cl 2 will not react with benzene, whereas FeCl 3 •Cl2 will.Due to the Lewis acidity of FeCl 3 , the Cl 2 bond is strongly polarized producing the superelectrophile [FeCl 4– ][Cl+]. This incipient Cl + is reactive enough to initiate the reaction.E +E+ = electrophileHHEEH+ H + eq. 1When discussing carbocation and radical stability we noted the ability of benzene rings tostabilize these structures through deloc...
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