Abstract

Carbon-13 kinetic isotope effects have been measured for the bimolecular reaction of 1-phenyl-1-bromoethane (I) and benzyl bromide (II) with alkoxide ion in alcohol solution. Compound I gave an effect, k12/k13, of 1.0032 ± 0.0005 for reaction with ethoxide ion in ethanol, while II gave k12/k13 = 1.0531 ± 0.0004 for reaction with methoxide ion in methanol. These surprisingly different effects are tentatively interpreted in terms of a model for the transition state having varying degrees of ionic character.

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