O CO₂Et This reaction involves an intramolecular aldol reaction followed by a retro aldol-like reaction. The steps i follows: ● Na OEt ethanol 1. Deprotonation to form enolate ion 1; 2. Cyclization via an intramolecular aldol reaction to form tetrahedral intermediate 2; 3. Collapse of the tetrahedral intermediate and bond cleavage to form enolate ion 3; 4. Protonation to form the final product. Write out the reaction on a separate sheet of paper, and then draw the structure of enolate ion 3. (+ [References] • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. . Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na+, I, in your answer. Y CO₂Et {n [F

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter24: Catalytic Carbon-carbon Bond Formation
Section: Chapter Questions
Problem 24.9P
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Please draw all structures (show the CO2Et structure) and label it clearly. Thank you!

O
O
+
CO₂Et
Na* OEt
ethanol
285
******
This reaction involves an intramolecular aldol reaction followed by a retro aldol-like reaction. The steps involved
follows:
1. Deprotonation to form enolate ion 1;
2. Cyclization via an intramolecular aldol reaction to form tetrahedral intermediate 2;
3. Collapse of the tetrahedral intermediate and bond cleavage to form enolate ion 3;
4. Protonation to form the final product.
Write out the reaction on a separate sheet of paper, and then draw the structure of enolate ion 3.
[References]
You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Do not include counter-ions, e.g., Na+, I, in your answer.
+-
0
» [ ]#
CO₂Et
F
4
Transcribed Image Text:O O + CO₂Et Na* OEt ethanol 285 ****** This reaction involves an intramolecular aldol reaction followed by a retro aldol-like reaction. The steps involved follows: 1. Deprotonation to form enolate ion 1; 2. Cyclization via an intramolecular aldol reaction to form tetrahedral intermediate 2; 3. Collapse of the tetrahedral intermediate and bond cleavage to form enolate ion 3; 4. Protonation to form the final product. Write out the reaction on a separate sheet of paper, and then draw the structure of enolate ion 3. [References] You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na+, I, in your answer. +- 0 » [ ]# CO₂Et F 4
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