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

Previous problemNext problem

5:50 minutes

Problem 56e

Textbook Question

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

Verified step by step guidance

Step 1: Identify the product structure and recognize the key functional groups. The product contains two carbonyl groups: one ketone and one ester. Additionally, there is a β-carbon with a methyl group attached, indicating a Michael addition reaction.

Step 2: Determine the Michael donor. A Michael donor is typically a nucleophile with an active methylene group (a CH2 group flanked by electron-withdrawing groups). In this case, the donor could be ethyl acetoacetate (CH3COCH2COOEt), which has an active methylene group between the ketone and ester functionalities.

Step 3: Determine the Michael acceptor. A Michael acceptor is typically an α,β-unsaturated carbonyl compound. In this case, the acceptor could be methyl vinyl ketone (CH2=CHCOCH3), which has a double bond conjugated to a ketone group.

Step 4: Describe the reaction mechanism. The Michael donor undergoes deprotonation at the active methylene group to form an enolate ion. This enolate ion then attacks the β-carbon of the Michael acceptor in a conjugate addition reaction, forming a new C-C bond.

Step 5: Explain the final product formation. After the conjugate addition, protonation of the intermediate occurs, followed by tautomerization if necessary, to yield the final product shown in the image. The product retains the ketone and ester functionalities, along with the newly formed β-carbon with a methyl group.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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, known as a Michael donor, adds to an α,β-unsaturated carbonyl compound, referred to as a Michael acceptor. This reaction is crucial in forming carbon-carbon bonds and is widely used in organic synthesis to create complex molecules. The nucleophile typically attacks the β-carbon of the unsaturated system, leading to the formation of a new carbon-carbon bond.

Michael Donors and Acceptors

Michael donors are compounds that possess a nucleophilic site, often containing electron-rich groups such as enolates or amines, which can donate electrons to an electrophilic site. Michael acceptors, on the other hand, are typically α,β-unsaturated carbonyl compounds that can accept electrons due to the presence of a partial positive charge on the β-carbon. Understanding the nature of these donors and acceptors is essential for predicting the outcomes of Michael addition reactions.

Synthesis Strategies in Organic Chemistry

Synthesis strategies in organic chemistry involve planning and executing a series of chemical reactions to construct a desired molecular structure. This includes selecting appropriate starting materials, reagents, and reaction conditions to achieve the target compound efficiently. In the context of Michael addition, identifying suitable Michael donors and acceptors is key to synthesizing complex products, as illustrated in the provided chemical structure.

Watch next

Master General Reaction with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

(f)

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.]

<IMAGE>

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.

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.

Show more practices