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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4:23 minutes

Problem 26

Textbook Question

Show how norbornane can be prepared from cyclopentadiene.

Verified step by step guidance

Step 1: Begin with cyclopentadiene, which is a five-membered ring containing two conjugated double bonds. This compound is highly reactive in Diels-Alder reactions due to its diene structure.

Step 2: Identify the dienophile needed for the Diels-Alder reaction. In this case, ethylene (C₂H₄) is a suitable dienophile because it contains a double bond that can react with the diene in cyclopentadiene.

Step 3: Perform the Diels-Alder reaction. The diene (cyclopentadiene) and the dienophile (ethylene) undergo a [4+2] cycloaddition reaction. This reaction forms a new six-membered ring structure, which is bicyclo[2.2.1]heptane, commonly known as norbornene.

Step 4: To convert norbornene into norbornane, perform a catalytic hydrogenation reaction. Use a catalyst such as palladium on carbon (Pd/C) or platinum (Pt) in the presence of hydrogen gas (H₂). This step will reduce the double bond in norbornene to form the fully saturated hydrocarbon, norbornane.

Step 5: Verify the structure of the final product, norbornane, which is a bicyclo[2.2.1]heptane with no double bonds. This confirms the successful preparation of norbornane from cyclopentadiene.

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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, forming a six-membered ring. In this context, cyclopentadiene acts as the diene, which can react with itself to form norbornene, a key intermediate in the synthesis of norbornane. This reaction is a fundamental method in organic synthesis for constructing cyclic compounds.

Norbornene

Norbornene is a bicyclic compound that can be derived from the Diels-Alder reaction of cyclopentadiene. It features a bridged bicyclic structure that is crucial for the subsequent hydrogenation step to produce norbornane. Understanding the structure and reactivity of norbornene is essential for grasping how to convert it into norbornane.

Hydrogenation

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to a compound, typically in the presence of a catalyst. In the preparation of norbornane from norbornene, hydrogenation converts the double bond in norbornene into a single bond, resulting in the saturated compound norbornane. This step is vital for completing the transformation from the unsaturated to the saturated bicyclic structure.

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