HChoose the best explanation for the proposed curved arrow mechanism in theactivation step of an acid-catalyzed hydration of a carbonyl.HHH9::Cl:ABThe carbonyl oxygen lone pair, a site of highelectron density, is attracted to the partially positiveproton of the hydronium ion, forming a bond.Donation from the lone pair into the σ* orbitalpopulates a high-energy antibonding orbital,resulting in H-O bond cleavage in hydronium ion.A new bond is formed between the carbonyl oxygenand the proton of the hydronium ion. At the sametime, the old bond breaks between the proton andoxygen of the hydronium ion.One of the hydrogen atoms of the hydronium ionmoves to the oxygen atom of the carbonyl. As theC hydrogen atom moves to form a new bond to thecarbonyl, the oxygen of the hydronium ion movesaway, forming water as a leaving group.The hydrogen atom of the hydronium ion attacksthe lone pair of the carbonyl oxygen, forming a newD O-H bond. At the same time, the oxygen atom of thehydronium ion breaks the bond to the O-H hydrogen,sending its positive charge to the carbonyl oxygen.

To solve this problem, we have to study the given reaction mechanism.

Answered: Choose the best explanation for the…

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

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 36E

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Question

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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