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 Forming Bridged Products

Organic Chemistry

16. Conjugated Systems

Diels-Alder Forming Bridged Products

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6:39 minutes

Problem 25h

Textbook Question

Predict the products of the following reactions.
(h) cyclopentadiene + methyl acrylate, CH₂=CH–COOCH₃

Verified step by step guidance

Step 1: Recognize the reaction type. Cyclopentadiene is a conjugated diene, and methyl acrylate (CH2=CH–COOCH3) is an alkene with an electron-withdrawing ester group. This setup suggests a Diels-Alder reaction, which is a [4+2] cycloaddition reaction between a diene and a dienophile.

Step 2: Analyze the diene and dienophile. Cyclopentadiene has two conjugated double bonds, making it an excellent diene. Methyl acrylate has a double bond adjacent to the ester group, which acts as an electron-withdrawing group, enhancing its reactivity as a dienophile.

Step 3: Determine the regioselectivity and stereochemistry. In the Diels-Alder reaction, the electron-withdrawing group (COOCH3) on the dienophile will typically orient itself to maximize interaction with the electron-rich diene. This leads to predictable regioselectivity in the product.

Step 4: Draw the cyclic product. The reaction forms a six-membered ring as the diene and dienophile combine. The ester group (COOCH3) will be attached to one of the carbons in the newly formed ring, and the stereochemistry will depend on the approach of the dienophile.

Step 5: Verify the product structure. Ensure that the product satisfies the rules of the Diels-Alder reaction, including conservation of the number of atoms and proper placement of substituents. The final product will be a bicyclic compound with the ester group attached to the appropriate position on the ring.

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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. In this case, cyclopentadiene acts as the diene, while methyl acrylate serves as the dienophile. This reaction is characterized by its stereospecificity and is widely used in organic synthesis to create complex cyclic structures.

Conjugated Dienes

Conjugated dienes are compounds that contain two double bonds separated by a single bond, allowing for resonance stabilization. This structure enhances their reactivity in cycloaddition reactions, such as the Diels-Alder reaction. Cyclopentadiene, with its two double bonds, is a classic example of a conjugated diene, making it highly reactive towards dienophiles like methyl acrylate.

Dienophile

A dienophile is a compound that contains a double bond and reacts with a diene in a Diels-Alder reaction. Dienophiles are typically electron-deficient, which makes them more reactive towards the electron-rich diene. Methyl acrylate, with its carbon-carbon double bond and electron-withdrawing ester group, is an effective dienophile that can participate in the cycloaddition with cyclopentadiene.

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Related Practice

Textbook Question

Predict the products of the following Diels–Alder reactions.

(a)

(b)

Textbook Question

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

(a)

(b)

(c)

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 3:

Textbook Question

The diene lactone shown in part (a) has one electron-donating group (-OR) and one electron-withdrawing group (C=O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.

b. The Diels–Alder product A is not very stable. Upon mild heating, it reacts to produce CO₂ gas and methyl benzoate (PhCOOCH₃), a very stable product. Explain how this strongly exothermic decarboxylation takes place. (Hint: Under the right conditions, the Diels–Alder reaction can be reversible.)

Textbook Question

Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reaction takes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of the product isomerizes to the exo isomer at 90 °C.

a. Draw and label the endo and exo isomers of the Diels–Alder adduct of furan and maleimide.

Textbook Question

b. Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.

Textbook Question

1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with

a. buta-1,3-diene

b. cyclopenta-1,3-diene

Textbook Question

Cyclopentadiene can react with itself in a Diels–Alder reaction. Draw the endo and exo products.

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Predict the products of the following reactions.(h) cyclopentadiene + methyl acrylate, CH2=CH–COOCH3

Key Concepts

Diels-Alder Reaction

Conjugated Dienes

Dienophile

Watch next

Predict the products of the following reactions.
(h) cyclopentadiene + methyl acrylate, CH₂=CH–COOCH₃