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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4:43 minutes

Problem 15a,b,c

Textbook Question

What dienes and dienophiles would react to give the following Diels–Alder products?
(a)
(b)
(c)

Verified step by step guidance

Step 1: Analyze the Diels–Alder product structure to identify the diene and dienophile components. The Diels–Alder reaction involves a conjugated diene reacting with a dienophile (an electron-deficient alkene or alkyne). Look for the cyclohexene ring in the product, which is characteristic of this reaction.

Step 2: For product (a), observe the cyclohexene ring with a ketone group (COCH₃) attached. The diene must have two conjugated double bonds, and the dienophile must contain a carbonyl group (C=O) to form this product. The diene is likely 1,3-cyclopentadiene, and the dienophile is methyl vinyl ketone (CH₂=CHCOCH₃).

Step 3: For product (b), observe the aromatic ring with a ketone group (COOCH₂CH₃) attached. The diene must have two conjugated double bonds, and the dienophile must contain an ester group (COOCH₂CH₃). The diene is likely 1,3-butadiene, and the dienophile is ethyl acrylate (CH₂=CHCOOCH₂CH₃).

Step 4: For product (c), observe the cyclohexene ring with a nitrile group (CN) attached. The diene must have two conjugated double bonds, and the dienophile must contain a nitrile group (C≡N). The diene is likely furan (a heterocyclic diene), and the dienophile is acrylonitrile (CH₂=CHCN).

Step 5: Verify the stereochemistry and regiochemistry of the products. The Diels–Alder reaction is stereospecific, meaning the stereochemistry of the diene and dienophile will influence the final product. Ensure that the substituents on the diene and dienophile align correctly to form the observed products.

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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 key method in organic synthesis for constructing cyclic compounds and is characterized by its stereospecificity and regioselectivity, making it a powerful tool for chemists.

Dienes

Dienes are organic compounds that contain two double bonds. They can be classified as conjugated, where the double bonds are separated by a single bond, or isolated, where the double bonds are separated by more than one single bond. Conjugated dienes are particularly important in Diels–Alder reactions due to their ability to stabilize the transition state and facilitate the cycloaddition process.

Dienophiles

Dienophiles are compounds that contain a double or triple bond and can react with dienes in the Diels–Alder reaction. They are typically electron-deficient, which enhances their reactivity towards the electron-rich diene. Common examples include alkenes and alkynes, often substituted with electron-withdrawing groups to increase their reactivity in the cycloaddition process.

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