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 Forming Bridged Products

Organic Chemistry

16. Conjugated Systems

Diels-Alder Forming Bridged Products

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4:19 minutes

Problem 14c

Textbook Question

Predict the products of the following proposed Diels–Alder reactions.
(c)

Verified step by step guidance

Step 1: Identify the reactants in the Diels–Alder reaction. The left structure is cyclopentadiene, which acts as the diene (a molecule with two conjugated double bonds). The right structure is a dienophile, specifically a molecule with a triple bond flanked by two cyano groups (-CN). The cyano groups are electron-withdrawing, making the dienophile highly reactive.

Step 2: Recall the mechanism of the Diels–Alder reaction. This reaction is a [4+2] cycloaddition, where the diene contributes four π-electrons and the dienophile contributes two π-electrons. The reaction forms a new six-membered ring.

Step 3: Analyze the regiochemistry. The electron-withdrawing cyano groups on the dienophile will direct the reaction such that the electron-rich ends of the diene align with the electron-deficient ends of the dienophile. This ensures the most stable product.

Step 4: Predict the stereochemistry. The Diels–Alder reaction is stereospecific, meaning that the stereochemistry of the dienophile is preserved in the product. Since the dienophile is linear, the product will not have stereochemical complexity.

Step 5: Draw the product structure. The reaction will result in a six-membered ring with two cyano groups attached to the carbons that were originally part of the triple bond in the dienophile. The double bonds in the diene will be converted into single bonds, and new σ-bonds will form between the diene and dienophile.

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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, making it a powerful tool for building complex molecular architectures.

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 is reactive towards the diene. The reactivity of these components is influenced by their electronic and steric properties, which can affect the outcome of the reaction and the stability of the products formed.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry involves the spatial arrangement of atoms in the resulting products. In Diels–Alder reactions, the orientation of substituents on the diene and dienophile can lead to different regioisomers and stereoisomers, which are crucial for predicting the final product's structure and properties.

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