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NUCLEOPHILIC AROMATIC SUBSTITUTION …
828 CHAPTER 18 THE CHEMISTRY OF ARYL HALIDES, VINYLIC HALIDES, AND PHENOLS. TRANSITION-METAL CATALYSISB ecause an aryl cation is forced to assume a nonoptimal geometry and hybridization, it has avery high energy. The electron-withdrawing polar effect of the ring double bonds also desta-bilizes an aryl cation, just as a double bond destabilizes a vinylic cation. Thus, SN1 reactionsof aryl halides do not occur because they would require the formation of carbocation interme-diates aryl cations with very high that an aryl cation is quite different from the cation formed in electrophilic AROMATIC substitu-tion (Eq.)
18.5 INTRODUCTION TO TRANSITION-METAL CATALYZED REACTIONS 831 18.5 Which of the two compounds in each of the following sets should react more rapidly in a …
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