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Which one is the major organic product obtained from the following reaction? 1. NaOCH₂CH3 CH3CH₂OH llam it OCH₂CH3 2. Ph 3. H₂O* Ph A C OCH₂CH3 OCH₂CH3 Ph Ph HO D B OCH₂CH3 Ph OCH₂CH

Which one is the major organic product obtained from the following reaction? 1. NaOCH₂CH3 CH3CH₂OH llam it OCH₂CH3 2. Ph 3. H₂O* Ph A C OCH₂CH3 OCH₂CH3 Ph Ph HO D B OCH₂CH3 Ph OCH₂CH

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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Having some trouble understanding the mechanism for claissen condensation required to complete this practice problem.  Any help with this would be greatly appreciated.  Thanks!

**Title:** Determining the Major Organic Product of a Claisen Condensation Reaction **Introduction:** This exercise involves analyzing the major organic product formed from the reaction between ethyl acetoacetate and benzaldehyde in the presence of an ethoxide base (NaOCH₂CH₃) and subsequent acidic workup (H₃O⁺). This type of reaction is typically known as a Claisen condensation followed by an aldol condensation. **Reaction Description:** - **Reactants:** The primary reactant is ethyl acetoacetate, a β-keto ester. It undergoes a reaction with benzaldehyde in the presence of sodium ethoxide dissolved in ethanol. - **Steps:** 1. NaOCH₂CH₃ (sodium ethoxide) in CH₃CH₂OH (ethanol) is used to form the enolate ion from ethyl acetoacetate. 2. The enolate reacts with benzaldehyde, undergoing nucleophilic addition. 3. The product is protonated using an acidic solution (H₃O⁺) to yield the final product. **Analysis of Possible Products:** Four potential products (A, B, C, D) are depicted following the reaction: - **Product A:** Contains a β-hydroxy keto structure with an ethoxy group and a phenyl (Ph) group. - **Product B:** Features a different arrangement of keto and phenyl groups, with no hydroxy group. - **Product C:** Displays a 1,3-diketone structure with ethoxy and phenyl groups. - **Product D:** Shows a hydroxy keto structure with an ethoxy group and phenyl group at a different position compared to A. **Conclusion:** The major product is typically determined by considering the stability of the resulting compound, stereochemistry, and reaction conditions. Under the conditions described, one can analyze which structural arrangement (from options A, B, C, or D) represents the most stable and favored product of the reaction pathways involved. **Note:** This problem is a classical organic chemistry puzzle, especially useful in understanding the mechanistic pathways of condensation reactions and their outcomes.
Transcribed Image Text:**Title:** Determining the Major Organic Product of a Claisen Condensation Reaction **Introduction:** This exercise involves analyzing the major organic product formed from the reaction between ethyl acetoacetate and benzaldehyde in the presence of an ethoxide base (NaOCH₂CH₃) and subsequent acidic workup (H₃O⁺). This type of reaction is typically known as a Claisen condensation followed by an aldol condensation. **Reaction Description:** - **Reactants:** The primary reactant is ethyl acetoacetate, a β-keto ester. It undergoes a reaction with benzaldehyde in the presence of sodium ethoxide dissolved in ethanol. - **Steps:** 1. NaOCH₂CH₃ (sodium ethoxide) in CH₃CH₂OH (ethanol) is used to form the enolate ion from ethyl acetoacetate. 2. The enolate reacts with benzaldehyde, undergoing nucleophilic addition. 3. The product is protonated using an acidic solution (H₃O⁺) to yield the final product. **Analysis of Possible Products:** Four potential products (A, B, C, D) are depicted following the reaction: - **Product A:** Contains a β-hydroxy keto structure with an ethoxy group and a phenyl (Ph) group. - **Product B:** Features a different arrangement of keto and phenyl groups, with no hydroxy group. - **Product C:** Displays a 1,3-diketone structure with ethoxy and phenyl groups. - **Product D:** Shows a hydroxy keto structure with an ethoxy group and phenyl group at a different position compared to A. **Conclusion:** The major product is typically determined by considering the stability of the resulting compound, stereochemistry, and reaction conditions. Under the conditions described, one can analyze which structural arrangement (from options A, B, C, or D) represents the most stable and favored product of the reaction pathways involved. **Note:** This problem is a classical organic chemistry puzzle, especially useful in understanding the mechanistic pathways of condensation reactions and their outcomes.
Expert Solution
Step 1: Introduction

First step of this reaction involve abstraction of most acidic hydrogen from active methylene compound. This reaction is known as Knoevangel reaction. 

In second step, carbanion attack Michel acceptor compound. This reaction is known as micheal addition reaction

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