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Choose the best explanation for the proposed curved arrow mechanism in the activation step of an acid-catalyzed hydration of a carbonyl.

Choose the best explanation for the proposed curved arrow mechanism in the activation step of an acid-catalyzed hydration of a carbonyl.

Chemistry
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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H Choose the best explanation for the proposed curved arrow mechanism in the activation step of an acid-catalyzed hydration of a carbonyl. H H H 9: :Cl: A B The carbonyl oxygen lone pair, a site of high electron density, is attracted to the partially positive proton of the hydronium ion, forming a bond. Donation from the lone pair into the σ* orbital populates a high-energy antibonding orbital, resulting in H-O bond cleavage in hydronium ion. A new bond is formed between the carbonyl oxygen and the proton of the hydronium ion. At the same time, the old bond breaks between the proton and oxygen of the hydronium ion. One of the hydrogen atoms of the hydronium ion moves to the oxygen atom of the carbonyl. As the C hydrogen atom moves to form a new bond to the carbonyl, the oxygen of the hydronium ion moves away, forming water as a leaving group. The hydrogen atom of the hydronium ion attacks the lone pair of the carbonyl oxygen, forming a new D O-H bond. At the same time, the oxygen atom of the hydronium ion breaks the bond to the O-H hydrogen, sending its positive charge to the carbonyl oxygen.
Transcribed Image Text:H Choose the best explanation for the proposed curved arrow mechanism in the activation step of an acid-catalyzed hydration of a carbonyl. H H H 9: :Cl: A B The carbonyl oxygen lone pair, a site of high electron density, is attracted to the partially positive proton of the hydronium ion, forming a bond. Donation from the lone pair into the σ* orbital populates a high-energy antibonding orbital, resulting in H-O bond cleavage in hydronium ion. A new bond is formed between the carbonyl oxygen and the proton of the hydronium ion. At the same time, the old bond breaks between the proton and oxygen of the hydronium ion. One of the hydrogen atoms of the hydronium ion moves to the oxygen atom of the carbonyl. As the C hydrogen atom moves to form a new bond to the carbonyl, the oxygen of the hydronium ion moves away, forming water as a leaving group. The hydrogen atom of the hydronium ion attacks the lone pair of the carbonyl oxygen, forming a new D O-H bond. At the same time, the oxygen atom of the hydronium ion breaks the bond to the O-H hydrogen, sending its positive charge to the carbonyl oxygen.
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