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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Problem 23c

Textbook Question

Give the diene and dienophile that could be used to make the following Diels–Alder products.
(c)

Verified step by step guidance

Identify the Diels–Alder product structure given in the problem. The Diels–Alder reaction involves a cycloaddition between a conjugated diene and a dienophile to form a six-membered ring.

Analyze the product to determine the positions of the new sigma bonds formed during the reaction. This will help in identifying the original diene and dienophile.

Recognize the six-membered ring in the product and locate the positions of the double bonds. The diene will contribute four carbon atoms and two double bonds, while the dienophile will contribute two carbon atoms and one double bond.

Determine the structure of the diene by identifying the four carbon atoms in the product that were originally part of the conjugated diene. The diene should have two adjacent double bonds.

Identify the dienophile by locating the two carbon atoms in the product that were originally part of the dienophile. The dienophile typically has an electron-withdrawing group to facilitate the reaction.

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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, typically an alkene or alkyne, to form a six-membered ring. This reaction is a cornerstone of organic synthesis due to its ability to form complex cyclic structures in a stereospecific manner. Understanding the electronic and steric requirements of both the diene and dienophile is crucial for predicting the outcome of the reaction.

Conjugated Diene

A conjugated diene is a molecule with two alternating double bonds separated by a single bond, allowing for electron delocalization across the pi system. This delocalization stabilizes the diene and is essential for its reactivity in the Diels–Alder reaction. The s-cis conformation of the diene is particularly reactive, as it allows the p orbitals to overlap effectively with those of the dienophile.

Dienophile

A dienophile is an electron-deficient alkene or alkyne that participates in the Diels–Alder reaction by reacting with a conjugated diene. The presence of electron-withdrawing groups on the dienophile enhances its reactivity by making it more electrophilic. Understanding the electronic nature of the dienophile is crucial for predicting the regioselectivity and stereochemistry of the Diels–Alder product.

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