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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7:39 minutes

Problem 41c

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.
(c)

Verified step by step guidance

Step 1: Identify the diene and dienophile within the molecule. The diene consists of two conjugated double bonds, while the dienophile is typically an electron-deficient alkene or alkyne. In this structure, the diene is the conjugated system on the left, and the dienophile is the double bond attached to the silicon group (SiMe3).

Step 2: Recognize that this is an intramolecular Diels–Alder reaction. Since the diene and dienophile are part of the same molecule, the reaction will form two new rings. The reaction proceeds via a concerted mechanism, where the π-electrons of the diene interact with the π-electrons of the dienophile.

Step 3: Predict the stereochemistry of the product. The reaction is stereospecific, meaning the stereochemistry of the starting material influences the stereochemistry of the product. The substituents on the diene and dienophile will determine the relative orientation of the newly formed rings. Use molecular models or visualization to predict the stereochemistry.

Step 4: Draw the product structure. The two new rings formed will be fused together, and the stereochemistry of the substituents must be carefully considered. The silicon group (SiMe3) and the oxygen-containing substituents will retain their relative positions based on the reaction mechanism.

Step 5: Verify the product by considering the regiochemistry and stereochemistry. Ensure that the electron flow during the reaction aligns with the formation of the two new rings and that the stereochemistry matches the expected outcome based on the starting material.

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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 significant in organic synthesis due to its ability to create complex cyclic structures efficiently. Understanding the mechanism, including the role of orbital overlap and the formation of new sigma bonds, is crucial for predicting the products and their stereochemistry.

Intramolecular Reactions

Intramolecular reactions occur when the reactants are part of the same molecule, allowing for a more favorable reaction environment and often leading to the formation of multiple rings. In the context of the Diels–Alder reaction, this means that the diene and dienophile are connected by a linker, which can influence the stereochemistry and the overall product structure. Recognizing how the molecular geometry affects the reaction pathway is essential for accurate predictions.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the Diels–Alder reaction, the stereochemical outcome is determined by the orientation of the diene and dienophile during the reaction. Predicting stereochemistry involves understanding concepts like cis/trans isomerism and the influence of substituents on the diene and dienophile, which can lead to different stereoisomers in the final product.

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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)

Textbook Question

What stereochemical result would you expect if the Diels–Alder reaction with the free α,β- unsaturated ketone was faster than reaction with the iminium-bound alkene?

Textbook Question

We predicted that the products would have a 1,2- or 1,4-relationship of the proper substituents. Draw the charge-separated resonance forms of the reactants to support these predictions.

(a) (b)

Textbook Question

(d)

Textbook Question

What is the major product when the methoxy substituent in the preceding reaction is bonded to C-2 of the diene rather than to C-1?

Textbook Question

Explain why the following compounds are not optically active:

a. the product obtained from the reaction of 1,3-butadiene with cis-1,2-dichloroethene

Textbook Question

Explain why the following compounds are not optically active:

b. the product obtained from the reaction of 1,3-butadiene with trans-1,2-dichloroethene

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