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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4: minutes

Problem 14e

Textbook Question

Predict the products of the following proposed Diels–Alder reactions.
(e)

Verified step by step guidance

Step 1: Identify the components of the Diels–Alder reaction. The reaction involves a conjugated diene (cyclohexadiene) and a dienophile (the molecule with two aldehyde groups attached to a triple bond). The diene will provide the π-electrons, while the dienophile will act as the electron-deficient partner.

Step 2: Analyze the dienophile. The triple bond in the dienophile is electron-deficient due to the electron-withdrawing aldehyde groups (-CHO). This makes it highly reactive toward the diene in the Diels–Alder reaction.

Step 3: Predict the regiochemistry. The electron-withdrawing groups on the dienophile will direct the reaction such that the new bonds form in a way that maximizes stability. The aldehyde groups will likely end up on the same side of the newly formed six-membered ring.

Step 4: Draw the product structure. The Diels–Alder reaction will result in a six-membered ring where the triple bond of the dienophile becomes a double bond, and the conjugated diene forms two new single bonds with the dienophile. The aldehyde groups will remain attached to the carbons where they were originally located.

Step 5: Confirm stereochemistry. The reaction is stereospecific, meaning the substituents on the dienophile (aldehyde groups) will retain their relative orientation (cis or trans) in the product. Since both aldehyde groups are on the same side of the dienophile, they will remain cis in the final product.

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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.

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 Diels–Alder reactions, as the diene can adopt an s-cis conformation, which is necessary for effective overlap with the dienophile's π orbitals during the reaction.

Dienophile

A dienophile is an electron-deficient alkene or alkyne that reacts with a diene in a Diels–Alder reaction. The presence of electron-withdrawing groups, such as carbonyls or nitriles, on the dienophile increases its reactivity by stabilizing the transition state, thus facilitating the cycloaddition process and influencing the regioselectivity of the product.

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