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

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5:42 minutes

Problem 30a

Textbook Question

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

Verified step by step guidance

Step 1: Identify the reactants in the Diels–Alder reaction. The diene is the conjugated system with two double bonds, and the dienophile is the molecule with one double bond and an electron-withdrawing group (in this case, the aldehyde group).

Step 2: Recall the mechanism of the Diels–Alder reaction. It is a [4+2] cycloaddition reaction where the diene contributes four π-electrons and the dienophile contributes two π-electrons to form a cyclic product.

Step 3: Analyze the stereochemistry. The Diels–Alder reaction is stereospecific, meaning the stereochemistry of the dienophile and diene will influence the stereochemistry of the product. The aldehyde group on the dienophile will determine the orientation of substituents in the product.

Step 4: Draw the cyclic product. Combine the diene and dienophile to form a six-membered ring. The new σ-bonds will form between the ends of the diene and the carbons of the dienophile's double bond. Ensure the aldehyde group is positioned correctly based on the stereochemistry.

Step 5: Confirm the regiochemistry and stereochemistry of the product. The electron-withdrawing group (aldehyde) on the dienophile will direct the reaction to form the most stable product, typically favoring endo addition (where substituents are oriented towards the newly formed π-system).

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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, resulting in the formation of a six-membered ring. This reaction is a key method in organic synthesis for constructing cyclic compounds and is characterized by its stereospecificity, meaning the stereochemistry of the reactants is preserved in the products.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of the Diels–Alder reaction, understanding stereochemistry is crucial for predicting the configuration of the product, as the reaction can lead to the formation of chiral centers and specific stereoisomers depending on the orientation of the reactants.

Electron Density and Reactivity

In organic chemistry, the reactivity of molecules is often influenced by the distribution of electron density. In the Diels–Alder reaction, the diene must be electron-rich, while the dienophile is typically electron-poor, often containing electron-withdrawing groups. This difference in electron density facilitates the formation of the new sigma bonds during the cycloaddition process.

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