Abstract
The kinetics of reaction between benzyl chloride and phenol (or substituted phenols) in the presence of sodium hydroxide have been investigated. A differential application of the effect of substituents on the reaction rate to distinguish between a rate-limiting oxygen or carbon attack has been attempted. Considerable scatter in the Hammett plot for the latter attack points to an essentially O-alkylation. The rate constants correlate well with pKa values of the different phenols. The influence of salt and solvent on the reaction rate suggests this reaction to be an ion-dipole one.
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Madhavan, K., Srinivasan, V.S. & Venkatasubramanian, N. Nucleophilic substitution at a benzylic carbon by an ambident nucleophile—A linear free energy relationship. Proc. Indian Acad. Sci. (Chem. Sci.) 88, 329–335 (1979). https://doi.org/10.1007/BF02844711
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DOI: https://doi.org/10.1007/BF02844711