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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3:55 minutes

Problem 89b

Textbook Question

How could the following compounds be synthesized using a Diels–Alder reaction?
b.

Verified step by step guidance

Step 1: Identify the product as a bicyclic compound formed via a Diels–Alder reaction. The Diels–Alder reaction involves a conjugated diene and a dienophile reacting to form a cyclohexene derivative.

Step 2: Analyze the structure of the product. The bicyclic system indicates that the reaction involved a cyclic diene. The ester group (CO₂CH₂CH₃) on the product suggests that the dienophile contained an electron-withdrawing group.

Step 3: Determine the diene. The presence of two methyl groups on the diene portion of the product suggests that the diene used was 2,3-dimethyl-1,3-butadiene, which is a conjugated diene.

Step 4: Determine the dienophile. The ester group in the product suggests that the dienophile was ethyl acrylate (CH₂=CHCO₂CH₂CH₃), which contains an electron-withdrawing group that enhances its reactivity in the Diels–Alder reaction.

Step 5: Combine the diene and dienophile. The reaction between 2,3-dimethyl-1,3-butadiene and ethyl acrylate under appropriate conditions (e.g., heat) would yield the bicyclic product shown in the image. The stereochemistry of the product is determined by the endo rule, favoring the formation of the endo 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 [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 with high stereoselectivity and regioselectivity. Understanding the reactivity of both the diene and the dienophile is crucial for predicting the outcome of the reaction.

Diene and Dienophile

In the context of the Diels–Alder reaction, a diene is a molecule that contains two double bonds, which can participate in the reaction, while a dienophile is a compound that contains a double or triple bond and reacts with the diene. The choice of diene and dienophile significantly influences the reaction's efficiency and the stereochemistry of the product. Recognizing suitable pairs is essential for successful synthesis.

Retrosynthetic Analysis

Retrosynthetic analysis is a method used in organic chemistry to deconstruct a target molecule into simpler precursor structures. This approach helps chemists identify potential synthetic routes, including the use of reactions like the Diels–Alder. By analyzing the target compound's structure, one can determine the necessary diene and dienophile, facilitating the planning of the synthesis.

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