The rate constants for the bromination of several

Chapter 19, Problem 19.84

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The rate constants for the bromination of several disubstituted stilbenes are given in the table below (J. Org. Chem. 1973, 38, 493 499). Given that the double bond of stilbene acts as the nucleophile, provide a reasonable explanation for the trend observed among the rate constants. X Y Br2 X Y Br Br X Y k (103 l/molmin) !OMe !OMe 220 !OMe !Me 114 !OMe !Cl 45 !OMe !NO2 5.2

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