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

16. Conjugated Systems

Diels-Alder Retrosynthesis

Organic Chemistry

16. Conjugated Systems

Diels-Alder Retrosynthesis

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1:20 minutes

Problem 89d

Textbook Question

How could the following compounds be synthesized using a Diels–Alder reaction?
d.

Verified step by step guidance

Step 1: Identify the product structure. The compound shown is a bicyclic system with two ketone groups and a conjugated double bond. This suggests it could be formed via a Diels–Alder reaction, which creates a six-membered ring by combining a diene and a dienophile.

Step 2: Analyze the product to determine the diene and dienophile components. The conjugated double bond in the product indicates the diene, while the ketone groups suggest the dienophile likely contains electron-withdrawing groups to enhance reactivity.

Step 3: Propose the diene. The diene must have two conjugated double bonds. A common choice for such reactions is 1,3-butadiene or a substituted diene that matches the product's structure.

Step 4: Propose the dienophile. The dienophile should contain two electron-withdrawing groups (such as carbonyl groups) to match the two ketone groups in the product. A suitable dienophile could be maleic anhydride or a similar compound.

Step 5: Combine the diene and dienophile in a Diels–Alder reaction. The reaction occurs under thermal conditions, where the diene and dienophile undergo a [4+2] cycloaddition to form the bicyclic product. Ensure the stereochemistry and regiochemistry align with the product structure.

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Key Concepts

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

Diels–Alder Reaction

The Diels–Alder reaction is a [4+2] cycloaddition reaction between a conjugated diene and a dienophile, resulting in the formation of a six-membered ring. This reaction is a powerful tool in organic synthesis due to its ability to create complex cyclic structures in a single step, often with high stereoselectivity. Understanding the reactivity of the diene and dienophile is crucial for predicting the outcome of the reaction.

Conjugated Dienes

Conjugated dienes are compounds that contain two double bonds separated by a single bond, allowing for resonance stabilization and increased reactivity in cycloaddition reactions. The ability of these compounds to adopt a s-cis conformation is essential for participating in the Diels–Alder reaction, as it positions the double bonds favorably for interaction with the dienophile.

Dienophile

A dienophile is an electron-deficient alkene or alkyne that reacts with a diene in the Diels–Alder reaction. The reactivity of the dienophile is influenced by its substituents; electron-withdrawing groups enhance its ability to participate in the reaction. Recognizing the nature of the dienophile is key to predicting the products formed in the synthesis process.

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