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

3:37 minutes

Problem 43a

Textbook Question

Predict the product of the following reactions. [When all of the reactions from this chapter are shown together, you must first decide which type of reaction each is. Is it a Diels–Alder, an electrocyclic, or a sigmatropic rearrangement? Drawing the product will be easier once this determination is made.]
(a)

Verified step by step guidance

Identify the type of reaction: Examine the reactants and determine if the reaction is a Diels–Alder, electrocyclic, or sigmatropic rearrangement. Look for characteristic features such as conjugated dienes for Diels–Alder reactions or cyclic systems for electrocyclic reactions.

Analyze the reactants: For a Diels–Alder reaction, identify the diene and the dienophile. For an electrocyclic reaction, identify the cyclic system and the number of π electrons involved. For a sigmatropic rearrangement, identify the migrating group and the type of shift (e.g., [1,3]-shift).

Apply the reaction mechanism: For a Diels–Alder reaction, draw the cyclic transition state and predict the stereochemistry of the product. For an electrocyclic reaction, determine whether the reaction is conrotatory or disrotatory based on the number of π electrons. For a sigmatropic rearrangement, draw the transition state and predict the new position of the migrating group.

Draw the product: Based on the mechanism and stereochemistry, draw the structure of the product. Ensure that all atoms and bonds are correctly represented, and check for any stereochemical implications.

Verify the product: Double-check the reaction type and mechanism to ensure that the predicted product is consistent with the known outcomes of such reactions. Consider any possible side reactions or alternative products that might form under the given conditions.

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 between a conjugated diene and a dienophile, forming a six-membered ring. It is a pericyclic reaction that proceeds via a concerted mechanism, meaning bonds are formed and broken simultaneously. This reaction is stereospecific and often used to synthesize complex cyclic structures in organic chemistry.

Electrocyclic Reaction

Electrocyclic reactions involve the conversion of a conjugated polyene into a cyclic compound through the rotation of a terminal bond. These reactions are governed by the Woodward-Hoffmann rules, which predict the stereochemistry based on the number of π electrons and whether the reaction is thermal or photochemical. Understanding these rules is crucial for predicting the product's stereochemistry.

Sigmatropic Rearrangement

Sigmatropic rearrangements are a type of pericyclic reaction where a σ-bond migrates across a π-system, resulting in a new σ-bond formation. These rearrangements are classified by the number of atoms involved in the migration, denoted as [i,j] shifts. The reaction's feasibility and stereochemistry are influenced by orbital symmetry and the number of electrons involved.

Watch next

Master General Features with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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?

Textbook Question

Assuming the diene approaches the dienophile from the top, predict the product of the following Diels–Alder reactions.

(c)

Textbook Question

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

Textbook Question

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

(c)

Textbook Question

Show the steps involved in the following reaction:

Textbook Question

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

(e)

(f)

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.

(a)

(b)

Textbook Question

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

(f)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap