Answered: 180 The starting material contains a…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Compelling evidence for the existence of a tetrahedral intermediate in
nucleophilic acyl substitution was obtained in a series of elegant
experiments carried out by Myron Bender in 1951. The key experiment
was the reaction of aqueous ⁻OH with ethyl benzoate (C₆H₅COOCH₂CH₃)
labeled at the carbonyl oxygen with ¹⁸O. Bender did not allow the
hydrolysis to go to completion, and then examined the presence of a
label in the recovered starting material. He found that some of the
recovered ethyl benzoate no longer contained a label at the carbonyl
oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral
intermediate.

180
The starting material contains a
label on the carbonyl oxygen.
Unlabelod starting
material was recovered.
ethyl bonzoate

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