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 Retrosynthesis

Organic Chemistry

16. Conjugated Systems

Diels-Alder Retrosynthesis

Previous problemNext problem

1:53 minutes

Problem 89c

Textbook Question

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

Verified step by step guidance

Step 1: Identify the product structure. The given compound is a cyclohexene derivative with a ketone functional group attached to the 2-position. This suggests that the compound could be synthesized via a Diels–Alder reaction, which forms a six-membered ring.

Step 2: Recall the Diels–Alder reaction mechanism. It involves a conjugated diene reacting with a dienophile to form a cyclohexene ring. The ketone group in the product indicates that the dienophile must contain a carbonyl group.

Step 3: Determine the diene. The cyclohexene ring in the product suggests that the diene should be a conjugated system, such as 1,3-butadiene, which can form the six-membered ring upon reaction.

Step 4: Determine the dienophile. The ketone group in the product suggests that the dienophile should be an α,β-unsaturated carbonyl compound, such as methyl vinyl ketone (CH2=CH-COCH3). This structure allows the carbonyl group to be incorporated into the final product.

Step 5: Combine the diene and dienophile. In the Diels–Alder reaction, 1,3-butadiene reacts with methyl vinyl ketone to form the cyclohexene ring with the ketone group at the 2-position. Ensure the reaction conditions are appropriate, typically involving heat or a Lewis acid catalyst to facilitate the cycloaddition.

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, resulting in the formation of a six-membered ring. This reaction is a key method in organic synthesis due to its ability to create complex cyclic structures with high stereoselectivity and regioselectivity. Understanding the mechanism, which involves the formation of a cyclic transition state, is crucial for predicting the products formed.

Conjugated Dienes

Conjugated dienes are compounds that contain two double bonds separated by a single bond, allowing for delocalization of π electrons. This delocalization enhances the reactivity of the diene in the Diels–Alder reaction, making it more nucleophilic. Recognizing the structure and stability of conjugated dienes is essential for determining their suitability as reactants in cycloaddition reactions.

Dienophile

A dienophile is an electron-deficient alkene or alkyne that reacts with a diene in the Diels–Alder reaction. The reactivity of the dienophile is influenced by substituents that can either withdraw or donate electron density, affecting the overall reaction rate and product formation. Identifying suitable dienophiles is critical for successfully synthesizing desired compounds through this reaction.

Watch next

Master Diels-Alder Retrosynthesis with a bite sized video explanation from Johnny

Start learning