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 (CeHgCoOCH,CH3) labeled at the carbonyl oxygen with 190. 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. The starting materiai contains a label on the carbonyl oxygen. CeH5 OCH,CH, CH5 OCH,CH, ethyl benzoate Unlabeled starting material was recovered.

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 (CeHgCoOCH,CH3) labeled at the carbonyl oxygen with 190. 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. The starting materiai contains a label on the carbonyl oxygen. CeH5 OCH,CH, CH5 OCH,CH, ethyl benzoate Unlabeled starting material was recovered.

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 innucleophilic acyl substitution was obtained in a series of elegantexperiments carried out by Myron Bender in 1951. The key experimentwas the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3)labeled at the carbonyl oxygen with 18O. Bender did not allow thehydrolysis to go to completion, and then examined the presence of alabel in the recovered starting material. He found that some of therecovered ethyl benzoate no longer contained a label at the carbonyloxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedralintermediate.
Aa.92.