Chapter3: Mechanisms
Section: Chapter Questions
Problem 140EQ
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To prove that the reaction of an ester with hydroxide ion is not an SN2 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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