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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3:40 minutes

Problem 101e

Textbook Question

Which diene and which dienophile could be used to prepare each of the following?
e.

Verified step by step guidance

Step 1: Recognize that the product shown is a result of a Diels-Alder reaction, which involves a conjugated diene and a dienophile reacting to form a cyclic compound.

Step 2: Analyze the structure of the product. The bicyclic ring system indicates that the reaction involved a conjugated diene with two double bonds and a dienophile with electron-withdrawing groups.

Step 3: Identify the diene. The two methyl groups on the diene portion suggest that the diene used was 2,3-dimethyl-1,3-butadiene, as it matches the substitution pattern in the product.

Step 4: Identify the dienophile. The ester groups (OCH₃) attached to the cyclohexene ring suggest that the dienophile was dimethyl maleate, which contains two electron-withdrawing ester groups that enhance reactivity in the Diels-Alder reaction.

Step 5: Conclude that the reaction involved 2,3-dimethyl-1,3-butadiene as the diene and dimethyl maleate as the dienophile to produce the given bicyclic compound.

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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 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 and regioselectivity. Understanding the reactivity of dienes and dienophiles is crucial for predicting the products of this reaction.

Diene and Dienophile Selection

Choosing the appropriate diene and dienophile is essential for a successful Diels-Alder reaction. The diene must be in an electron-rich state, typically possessing conjugated double bonds, while the dienophile is often electron-deficient, featuring groups like carbonyls or nitro groups. The electronic and steric properties of both reactants influence the reaction's efficiency and the resulting product's structure.

Retrosynthetic Analysis

Retrosynthetic analysis is a strategy used in organic chemistry to deconstruct a target molecule into simpler precursor structures. This approach helps chemists identify potential starting materials and reaction pathways to synthesize complex compounds. In the context of the Diels-Alder reaction, it involves determining suitable dienes and dienophiles that can yield the desired product through a logical breakdown of the molecular structure.

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