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

Previous problemNext problem

4:35 minutes

Problem 13a

Textbook Question

In each Diels–Alder reaction shown, predict the product that will result.
(a)

Verified step by step guidance

Identify the diene and the dienophile in the reaction. In this case, the diene is the compound with two conjugated double bonds, and the dienophile is the compound with the carbonyl groups.

Recognize that the Diels–Alder reaction is a [4+2] cycloaddition, where the diene contributes four π-electrons and the dienophile contributes two π-electrons to form a six-membered ring.

Consider the stereochemistry of the reaction. The Diels–Alder reaction is stereospecific, meaning that the stereochemistry of the dienophile is preserved in the product. If the dienophile is cis, the substituents will be on the same side in the product.

Analyze the regiochemistry of the reaction. The electron-withdrawing groups on the dienophile will direct the reaction to form the most stable product, often resulting in endo selectivity, where substituents are oriented towards the larger bridge in the bicyclic system.

Draw the product by forming a new six-membered ring between the diene and dienophile, ensuring that the stereochemistry and regiochemistry are correctly represented. The product will be a bicyclic compound with the newly formed ring and the original substituents from the dienophile.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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. It is a pericyclic reaction that proceeds through a concerted mechanism, meaning bonds are formed and broken simultaneously. This reaction is stereospecific, often preserving the stereochemistry of the reactants in the product.

Stereochemistry in Diels-Alder Reactions

Stereochemistry plays a crucial role in Diels-Alder reactions, as the configuration of the diene and dienophile affects the stereochemistry of the product. The reaction can produce endo or exo products, with the endo product typically favored due to secondary orbital interactions. The orientation of substituents in the reactants influences the stereochemical outcome of the reaction.

Endo and Exo Selectivity

Endo and exo selectivity refers to the preference for forming one stereoisomer over another in Diels-Alder reactions. The endo product is favored when the substituents on the dienophile are oriented towards the diene's π system, allowing for stabilizing interactions. This preference is often explained by the endo rule, which suggests that secondary orbital interactions stabilize the transition state leading to the endo product.

Watch next

Master General Features with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

An important variation of the Diels–Alder reaction is intramolecular, in which the diene and the dienophile are connected. This type of Diels–Alder reaction makes two new rings. Draw the compound produced in each of these examples; try to predict stereochemistry (using models will help). In some cases, Lewis acid catalysts are used; that can be ignored for this problem.

(d)

Textbook Question

What is the major product when the methoxy substituent in the preceding reaction is bonded to C-2 of the diene rather than to C-1?

Textbook Question

Explain why the following compounds are not optically active:

a. the product obtained from the reaction of 1,3-butadiene with cis-1,2-dichloroethene

Textbook Question

Explain why the following compounds are not optically active:

b. the product obtained from the reaction of 1,3-butadiene with trans-1,2-dichloroethene

Textbook Question

By forming a Lewis acid–Lewis base complex with the dienophile, Lewis acids are able to increase the rate of Diels–Alder reactions. Why might this be true?

Textbook Question

Which of the following concerted reactions would have a more stable transition state? Why?

Textbook Question

How could the following compounds be synthesized using a Diels–Alder reaction?

Multiple Choice

Predict the major, organic product for the following reaction.

Show more practices