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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3:50 minutes

Problem 77a

Textbook Question

The A ring of cortisone (a steroid) is formed by a Diels–Alder reaction using the two reactants shown here. What is the product of this reaction?

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Identify the two reactants in the Diels–Alder reaction: one is the diene (a molecule with two conjugated double bonds), and the other is the dienophile (a molecule with a double or triple bond that reacts with the diene). Analyze the structures provided in the problem to determine which is which.

Understand 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. This reaction forms a six-membered ring.

Orient the diene and dienophile correctly: ensure that the diene is in the s-cis conformation (both double bonds on the same side of the single bond) to allow for proper orbital overlap. Check for any substituents on the diene or dienophile that may influence regioselectivity or stereoselectivity.

Predict the product: combine the diene and dienophile to form a six-membered ring. Pay attention to the stereochemistry of the product, as the Diels–Alder reaction is stereospecific. If the dienophile has substituents, their stereochemistry (cis or trans) will be preserved in the product.

Verify the structure of the product: ensure that the newly formed six-membered ring matches the A ring of cortisone. Double-check the positions of any substituents and the stereochemistry to confirm the product aligns with the expected outcome.

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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 and regioselectivity. Understanding the mechanism and the orientation of the reactants is crucial for predicting the product.

Steroid Structure

Steroids are a class of organic compounds characterized by a core structure of four fused carbon rings, known as the steroid nucleus. The specific arrangement of functional groups and the stereochemistry of these rings influence the biological activity and properties of steroids. Recognizing the A, B, C, and D rings in steroids is essential for understanding their synthesis and reactivity.

Reactant Identification

Identifying the correct reactants in a Diels–Alder reaction is critical for predicting the product. The diene must be in an appropriate conformation to react with the dienophile, which can be an alkene or alkyne. Understanding the electronic and steric properties of the reactants helps in determining the feasibility of the reaction and the nature of the resulting product.

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Write a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.

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What two products are formed from each of the following reactions?

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The C ring of estrone (a steroid) is formed by a Diels–Alder reaction using the two reactants shown here. What is the product of this reaction?

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As many as 18 different Diels–Alder products can be obtained by heating a mixture of 1,3-butadiene and 2-methyl-1,3-butadiene. Identify the products.

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Identify the product of the following reaction.

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How would the following substituents affect the rate of a Diels–Alder reaction?

c. an electron-withdrawing substituent in the diene

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