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

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4:37 minutes

Problem 47f

Textbook Question

What diene and what dienophile should be used to synthesize the following?
f.

Verified step by step guidance

Analyze the target molecule: The structure contains a six-membered ring with one double bond and two carboxylic acid groups attached at the 1 and 4 positions. This suggests that the molecule was formed via a Diels-Alder reaction.

Identify the diene: The Diels-Alder reaction requires a conjugated diene. In this case, the diene should be a molecule with two conjugated double bonds that can form the six-membered ring upon reaction.

Identify the dienophile: The dienophile is typically an electron-deficient alkene or alkyne. Here, the two carboxylic acid groups in the product suggest that the dienophile should contain two electron-withdrawing groups, such as two carboxylic acid groups or their derivatives.

Determine the orientation: The stereochemistry of the product indicates that the reaction occurred in a specific orientation. The cis relationship between the carboxylic acid groups suggests that the dienophile was likely a cis-substituted alkene.

Combine the components: Based on the analysis, the diene could be 1,3-butadiene, and the dienophile could be cis-1,2-ethene-dicarboxylic acid (maleic acid). These reactants would undergo a Diels-Alder reaction to form the given 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 cycloaddition reaction between a conjugated diene and a dienophile, forming a six-membered ring. This reaction is a key method in organic synthesis for constructing complex cyclic structures and is characterized by its stereospecificity and regioselectivity. Understanding the mechanism and the requirements for both the diene and dienophile is essential for predicting the products formed.

Conjugated Dienes

Conjugated dienes are compounds that contain two double bonds separated by a single bond, allowing for resonance stabilization and increased reactivity in cycloaddition reactions. The ability of these dienes to adopt an 's-cis' conformation is crucial for their participation in the Diels-Alder reaction, as this conformation allows for optimal 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 the Diels-Alder reaction. The reactivity of a dienophile is influenced by its substituents; electron-withdrawing groups enhance its ability to participate in the reaction. Identifying the appropriate dienophile is critical for achieving the desired product, as it determines the regioselectivity and stereochemistry of the resulting cyclohexene derivative.

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