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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7:20 minutes

Problem 33i

Textbook Question

Show how Diels–Alder reactions might be used to synthesize the following compounds.
(i)

Verified step by step guidance

Step 1: Identify the target molecule as a bicyclic compound with a sulfone group and two cyano groups attached to the bridgehead carbons. This structure suggests that it could be synthesized using a Diels–Alder reaction followed by functional group modifications.

Step 2: Recognize that the Diels–Alder reaction involves a conjugated diene and a dienophile. The bicyclic structure indicates that the reaction likely involves a cyclic diene and a dienophile with electron-withdrawing groups to facilitate the reaction.

Step 3: Propose the diene as cyclopentadiene, which is commonly used in Diels–Alder reactions to form bicyclic systems. Cyclopentadiene has the necessary conjugated double bonds to act as the diene.

Step 4: Suggest the dienophile as a molecule containing electron-withdrawing groups such as cyano groups (–CN). A possible dienophile could be fumaronitrile (trans-1,2-dicyanoethene), which has two cyano groups that can stabilize the transition state during the reaction.

Step 5: After the Diels–Alder reaction forms the bicyclic intermediate, introduce the sulfone group (–SO2) through an oxidation reaction. This can be achieved by treating the intermediate with a sulfonylating agent such as sulfur dioxide (SO2) or a sulfonyl chloride under appropriate conditions.

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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 powerful tool in organic synthesis due to its ability to create complex cyclic structures in a single step, often with high stereoselectivity and regioselectivity.

Conjugated Dienes

Conjugated dienes are compounds that contain two double bonds separated by a single bond, allowing for resonance stabilization. This property enhances their reactivity in Diels–Alder reactions, as the electron-rich diene can effectively interact with an electron-deficient dienophile, facilitating the cycloaddition process.

Stereochemistry in Diels–Alder Reactions

Stereochemistry plays a crucial role in Diels–Alder reactions, as the orientation of substituents on the diene and dienophile can influence the final product's configuration. The reaction typically proceeds with a concerted mechanism, preserving the stereochemistry of the reactants, which is essential for predicting the structure of the synthesized compound.

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