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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9:11 minutes

Problem 36a

Textbook Question

Predict the product of the Diels–Alder reactions shown.
(a)

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Identify the diene and the dienophile in the reaction. The diene is a conjugated system with two double bonds, and the dienophile is typically an alkene or alkyne with electron-withdrawing groups.

Ensure the diene is in the s-cis conformation, which is necessary for the Diels-Alder reaction to occur. If it is not, consider any possible rotations or conformational changes.

Align the diene and dienophile so that the p orbitals can overlap effectively. This involves bringing the diene and dienophile close together in a way that allows for the formation of new sigma bonds.

Draw the transition state of the reaction, showing the cyclic overlap of the p orbitals. This is a concerted process where bonds are broken and formed simultaneously.

Predict the product by forming a six-membered ring. The new sigma bonds form between the ends of the diene and the dienophile, resulting in a cyclohexene derivative. Consider any stereochemistry involved, as the reaction is stereospecific.

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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 between a conjugated diene and a dienophile, typically forming a six-membered ring. It is a pericyclic reaction that proceeds via a concerted mechanism, meaning bonds are formed simultaneously without intermediates. This reaction is stereospecific, often preserving the stereochemistry of the reactants in the product.

Conjugated Diene

A conjugated diene consists of two double bonds separated by a single bond, allowing for electron delocalization across the π-system. This delocalization stabilizes the diene and makes it reactive in cycloaddition reactions like the Diels–Alder. The s-cis conformation of the diene is crucial for effective overlap with the dienophile's π-orbitals during the reaction.

Dienophile

A dienophile is an alkene or alkyne that reacts with a diene in the Diels–Alder reaction. It typically contains electron-withdrawing groups that enhance its reactivity by making the π-bond more electrophilic. The stereochemistry of the dienophile influences the stereochemistry of the resulting cyclohexene product, making its orientation important in predicting the reaction outcome.

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Related Practice

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

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.

Textbook Question

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

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?

Textbook Question

Predict the product of the following Diels–Alder reactions. Where a racemic mixture is produced, show both enantiomers and explain how each is formed.

(d)

Textbook Question

Figure 22.16(a) <IMAGE> shows a unique example where the Diels–Alder reaction gives a single product (no enantiomers) regardless of whether the diene attacks the dienophile from the top or bottom.

(a) Show the product of the diene attacking from the bottom and confirm that the same product is obtained.

(b) What is special about this product that makes this true?

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Predict the product of the Diels–Alder reactions shown. (a)

Key Concepts

Diels–Alder Reaction

Conjugated Diene

Dienophile

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Predict the product of the Diels–Alder reactions shown.
(a)