Answered: 18 Q. 18 OCH2CH3 OCH,CH3 + HÖ: +

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18 Q. 18 OCH2CH3 OCH,CH3 + HÖ: +

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter22: Proteins

Section: Chapter Questions

Problem 22.59P: 22-59 What is the effect of salt bridges on the tertiary structure of proteins?

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Question

To prove that the reaction of an ester with hydroxide ion is not an S_N2 reaction but, instead, forms a tetrahedral intermediate that subsequently collapses, the products obtained after allowing hydroxide ion to react with an ester containing an isotopically labeled carbonyl oxygen (¹⁸O) were isolated. One of the products was isotopically labeled hydroxide ion. Explain how obtaining this product proves that a tetrahedral intermediate was formed.

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