Question: Explain why the halo-substituted benzenes have the relative reactivities shown in Table 16.1. Table 16.1 The Effects of Substituents on the Reactivtty of a Benzene

Explain why the halo-substituted benzenes have the relative reactivities shown in Table 16.1.

Table 16.1 The Effects of Substituents on the Reactivtty of a Benzene Ring Toward Electrophilc Substitution Activating substituents Most activating NH2 -NHR NR2 -OH -OR Strongly activating directing Ar -CH-CHR Weakly activating Standard of comparison-H -F -Cl -Br Weakly Meta directing Cl CEN SO3H Strongly deactivating NHR, R, NO2 Most deactivating

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Table 161 shows that fluorine is the least deactivating of the halogen substituents and iodine is the most deactivating We know that fluorine is the most electronegative of the halogens which means that it is best at withdrawing electrons inductively Fluorine is also best at donating electrons by resonance because its 2p orbitalcompared with the 3p orbital of chlorine the 4p orbital of bromine or the 5p orbital of iodinecan better overlap with the 2p orbital of carbon So the fluorine substituent ... View full answer

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