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 Reaction

Organic Chemistry

16. Conjugated Systems

Diels-Alder Reaction

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Problem 24

Textbook Question

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Verified step by step guidance

Identify the reactants: Benzyne is generated in situ from chlorobenzene and NaOH under heat. Cyclopentadiene is the diene in this Diels–Alder reaction.

Understand the Diels–Alder reaction mechanism: This is a [4+2] cycloaddition reaction where the diene (cyclopentadiene) reacts with the dienophile (benzyne) to form a six-membered ring.

Analyze the structure of benzyne: Benzyne has a triple bond within a benzene ring, making it highly reactive as a dienophile. The triple bond will participate in the reaction.

Draw the reaction: Orient cyclopentadiene so that its conjugated double bonds align with the triple bond of benzyne. The π-electrons from the diene and dienophile will interact to form two new σ-bonds, creating a bicyclic product.

Predict the product: The product will be a bicyclic compound with a six-membered ring fused to the original cyclopentadiene structure. Ensure to account for stereochemistry if applicable.

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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 significant in organic synthesis due to its ability to create complex cyclic structures in a single step. The reactivity of the diene and dienophile, as well as the stereochemistry of the products, are crucial factors in predicting the outcome of the reaction.

Benzyne

Benzyne is a highly reactive intermediate that contains a triple bond between two carbon atoms in a benzene ring. It can be generated from chlorobenzene through dehydrohalogenation, typically using strong bases like NaOH. Due to its unique structure, benzyne acts as a potent dienophile in Diels–Alder reactions, allowing it to react with various dienes, such as cyclopentadiene.

Cyclopentadiene

Cyclopentadiene is a five-membered cyclic diene that is commonly used in Diels–Alder reactions due to its high reactivity. It has two double bonds that can participate in the cycloaddition process, making it an effective partner for dienophiles like benzyne. The structure and electron-rich nature of cyclopentadiene enhance its ability to form stable adducts with reactive dienophiles, leading to diverse synthetic applications.

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Textbook Question

Predict the products of the following proposed Diels–Alder reactions.

(b)

Textbook Question

Predict the products of the following proposed Diels–Alder reactions.

(a)

Textbook Question

Predict the products of the following proposed Diels–Alder reactions. Include stereochemistry where appropriate.

(d)

Textbook Question

Predict the products of the following Diels–Alder reactions.

(c)

(d)

Textbook Question

Provide a mechanism of the Diels–Alder reaction shown and predict the regioisomer that will form.

Textbook Question

Predict the product of the Diels–Alder reactions shown.

(a)

Textbook Question

While not covered explicitly in this chapter, the ene reaction occurs similarly to the Diels–Alder reaction but replaces the electrons from one bond in the diene with the electrons in a C―H bond. Draw the mechanism for the following reaction. [Number the carbons and draw in the hydrogens of the product. And, of course, make a note of bonds formed and bonds broken.]

Textbook Question

Diene A participates in a fast and efficient Diels–Alder reaction with maleic anhydride, the powerful dienophile from Assessment 22.9. However, the related diene B does not undergo a Diels–Alder reaction. Why?

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