Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

25. Condensation Chemistry

Michael Addition

Organic Chemistry

25. Condensation Chemistry

Michael Addition

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4:21 minutes

Problem 52

Textbook Question

In Solved Problem 22-9, the target molecule was synthesized using a Michael addition to form the bond that is β,γ to the upper carbonyl group. Another approach is to use a Michael addition to form the bond that is β,γ to the other (lower) carbonyl group. Show how you would accomplish this alternative synthesis.

Verified step by step guidance

Identify the target molecule and analyze its structure to determine the β,γ bond that needs to be formed relative to the lower carbonyl group. This will help in planning the Michael addition reaction.

Choose an appropriate Michael donor (nucleophile) and Michael acceptor (electrophile). The Michael donor should be an enolate or a compound capable of forming an enolate, while the Michael acceptor should contain an α,β-unsaturated carbonyl group.

Generate the enolate ion from the Michael donor by treating it with a suitable base, such as hydroxide (OH⁻) or an alkoxide (RO⁻). This step activates the donor for nucleophilic attack.

Perform the Michael addition reaction by allowing the enolate ion to attack the β-carbon of the α,β-unsaturated carbonyl compound (Michael acceptor). This forms a new C-C bond at the β,γ position relative to the lower carbonyl group.

After the Michael addition, perform any necessary workup steps, such as protonation of the intermediate, to obtain the final product. Verify that the product matches the target molecule with the desired β,γ bond formed relative to the lower carbonyl group.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Michael Addition

Michael addition is a nucleophilic addition reaction where a nucleophile adds to an α,β-unsaturated carbonyl compound. This reaction typically involves the addition of a carbanion or another nucleophile to the β-carbon of the unsaturated system, resulting in the formation of a new carbon-carbon bond. Understanding this mechanism is crucial for manipulating the position of the bond formed in the synthesis of complex molecules.

Carbonyl Chemistry

Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), play a significant role in organic synthesis. The reactivity of carbonyl groups allows for various transformations, including nucleophilic additions and condensations. In the context of the question, recognizing the role of the carbonyl groups in directing the Michael addition is essential for planning the alternative synthesis pathway.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions like the Michael addition, the stereochemical outcome can influence the properties of the final product. Understanding stereochemistry is vital when considering alternative synthesis routes, as it can determine the selectivity and yield of the desired compound.

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Related Practice

Textbook Question

Write equations showing the expected products of the following enamine alkylation and acylation reactions. Then give the final products expected after hydrolysis of the iminium salts.

(d) piperidine enamine of cyclopentanone + methyl vinyl ketone

Textbook Question

Show how you would accomplish each conversion using an enamine synthesis with pyrrolidine as the secondary amine.

(a) cyclopentanone → 2-allylcyclopentanone

(b) pentan-3-one → 2-methyl-1-phenylpentan-3-one

Textbook Question

The following covalent inhibitor blocks function in a protease found in the porcine epidemic diarrhea virus by reacting with a cysteine amino acid residue (shown below) in the active site. Draw the expected complex that forms between the inhibitor and the enzyme active site (J. Med. Chem. 2017, 60, 3212–3216.) [Assume the presence of active site bases if you need them.]

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Textbook Question

Show how the following products might be synthesized from suitable Michael donors and acceptors.

(e)

Textbook Question

Show how cyclohexanone might be converted to the following δ-diketone (Hint: Stork).

Multiple Choice

Determine the product in the following conjugated addition reaction.

Multiple Choice

Determine the product in the following conjugated addition reaction.

Multiple Choice

Determine the product in the following conjugated addition reaction