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Give the expected product of the following Michael addition. base 6.

Give the expected product of the following Michael addition. base 6.

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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**Question:** 6. Give the expected product of the following *Michael addition*. **Reaction Scheme:** The reactants for the Michael addition reaction are presented as follows: - The first compound is a molecule with a benzene ring (phenyl group) attached to a double-bonded carbon, which is further connected to a carbonyl group (C=O). - The second compound is a cyclic anhydride, specifically a five-membered ring with two carbonyl groups, one at each end. An arrow pointing to the right indicates the direction of the reaction, with the word "base" located under the arrow, signifying that a base catalyst is used for the reaction. **Graph/Diagram:** The image includes the structural formulas of the reactants and a large empty rectangular box which indicates the space where the product of the Michael addition is to be inserted. **Reaction Explanation:** In a Michael addition, the base deprotonates the donor compound, generating an enolate ion, which then attacks the β-position of an α,β-unsaturated carbonyl acceptor. Given this general mechanism: - The phenyl ring compound with the carbonyl group acts as the Michael acceptor. - The cyclic anhydride compound acts as the Michael donor, with the enolate form attacking the acceptor molecule. The expected product will be the addition of the donor molecule across the double bond of the acceptor, generally forming a 1,5-dicarbonyl compound, where the new bond forms at the β-carbon (relative to the original carbonyl) of the acceptor. **Educational Notes:** - *Michael Addition* is a type of conjugate addition where an enolate ion adds to an α,β-unsaturated carbonyl compound. - The role of the base is crucial as it generates the enolate ion from the Michael donor. - Understanding this type of reaction is essential for learning about nucleophilic addition and its application in synthetic organic chemistry.
Transcribed Image Text:**Question:** 6. Give the expected product of the following *Michael addition*. **Reaction Scheme:** The reactants for the Michael addition reaction are presented as follows: - The first compound is a molecule with a benzene ring (phenyl group) attached to a double-bonded carbon, which is further connected to a carbonyl group (C=O). - The second compound is a cyclic anhydride, specifically a five-membered ring with two carbonyl groups, one at each end. An arrow pointing to the right indicates the direction of the reaction, with the word "base" located under the arrow, signifying that a base catalyst is used for the reaction. **Graph/Diagram:** The image includes the structural formulas of the reactants and a large empty rectangular box which indicates the space where the product of the Michael addition is to be inserted. **Reaction Explanation:** In a Michael addition, the base deprotonates the donor compound, generating an enolate ion, which then attacks the β-position of an α,β-unsaturated carbonyl acceptor. Given this general mechanism: - The phenyl ring compound with the carbonyl group acts as the Michael acceptor. - The cyclic anhydride compound acts as the Michael donor, with the enolate form attacking the acceptor molecule. The expected product will be the addition of the donor molecule across the double bond of the acceptor, generally forming a 1,5-dicarbonyl compound, where the new bond forms at the β-carbon (relative to the original carbonyl) of the acceptor. **Educational Notes:** - *Michael Addition* is a type of conjugate addition where an enolate ion adds to an α,β-unsaturated carbonyl compound. - The role of the base is crucial as it generates the enolate ion from the Michael donor. - Understanding this type of reaction is essential for learning about nucleophilic addition and its application in synthetic organic chemistry.
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