Copy the figure shown below onto your scratch paper. Вох 1 Вох 2 Box 3 heat -> NaOH CH3 Products Вох 5 Box 4 NaOH H20 Then, complete the figure on your scratch paper by drawing out the intermediates and arrow-pushing mechanism in Boxes 1-5 that explain the formation of the aldol condensation products shown. You should start your arrow- pushing in Box 1, and you will use all boxes. Now, report the formal charges (+,0,-) that appear on OA and Cg atoms in each box, and match the contents of each box to a single phrase (A-H) that best describes the mechanistic step that occurs in each box. A phrase may be used more than once. A. An enol attacks, and a water leaving group leaves. B. An enolate attacks, and a hydroxide leaving group leaves. C. An O atom is protonated, and an O atom is deprotonated. D. AC atom is protonated, and an O atom is deprotonated. E. An O atom is protonated, and a C atom is deprotonated. F. An enolate nucleophile attacks, and a C-O T bond breaks G. A hydroxide nucleophile attacks, and a C-C m bond breaks. Hân enol nucleonhile attacks d hreaks

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 22CTQ
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QUESTION 33
Copy the figure shown below onto your scratch paper.
Box 1
Вох 2
Box 3
heat
OA
NaOH
CH3
Products
Вох 5
Box 4
OA
NaOH
H20
Then, complete the figure on your scratch paper by drawing out the intermediates and arrow-pushing mechanism in Boxes 1-5 that explain the formation of the aldol condensation products shown. You should start your arrow-
pushing in Box 1, and you will use all boxes.
Now, report the formal charges (+,0,-) that appear on OA and Ca atoms in each box, and match the contents of each box to a single phrase (A-H) that best describes the mechanistic step that occurs in each box. A phrase may be
used more than once.
A. An enol attacks, and a water leaving group leaves.
B. An enolate attacks, and a hydroxide leaving group leaves.
C. An O atom is protonated, and an O atom is deprotonated.
D. AC atom is protonated, and an O atom is deprotonated.
E. An O atom is protonated, and a C atom is deprotonated.
F. An enolate nucleophile attacks, and a C-0 m bond breaks.
G. A hydroxide nucleophile attacks, and a C-C bond breaks.
H. An enol nucleophile attacks, and a C-O T bond breaks.
OA formal charge (+,0,-) Ca formal charge (±,0,:) Phrase (A-H)
Вох 1: 0
Воx 2:
Вох 3:
Воx 4:
Box 5:
Products: 0
Transcribed Image Text:QUESTION 33 Copy the figure shown below onto your scratch paper. Box 1 Вох 2 Box 3 heat OA NaOH CH3 Products Вох 5 Box 4 OA NaOH H20 Then, complete the figure on your scratch paper by drawing out the intermediates and arrow-pushing mechanism in Boxes 1-5 that explain the formation of the aldol condensation products shown. You should start your arrow- pushing in Box 1, and you will use all boxes. Now, report the formal charges (+,0,-) that appear on OA and Ca atoms in each box, and match the contents of each box to a single phrase (A-H) that best describes the mechanistic step that occurs in each box. A phrase may be used more than once. A. An enol attacks, and a water leaving group leaves. B. An enolate attacks, and a hydroxide leaving group leaves. C. An O atom is protonated, and an O atom is deprotonated. D. AC atom is protonated, and an O atom is deprotonated. E. An O atom is protonated, and a C atom is deprotonated. F. An enolate nucleophile attacks, and a C-0 m bond breaks. G. A hydroxide nucleophile attacks, and a C-C bond breaks. H. An enol nucleophile attacks, and a C-O T bond breaks. OA formal charge (+,0,-) Ca formal charge (±,0,:) Phrase (A-H) Вох 1: 0 Воx 2: Вох 3: Воx 4: Box 5: Products: 0
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