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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3:43 minutes

Problem 25d

Textbook Question

Predict the products of the following reactions.
(d) furan + trans-1,2-dicyanoethylene

Verified step by step guidance

Step 1: Identify the reactants. Furan is a five-membered aromatic heterocyclic compound containing oxygen. The second reactant is trans-1,2-dicyanoethylene, which is an alkene with two cyano groups (-CN) attached to the double bond in a trans configuration.

Step 2: Recognize the type of reaction. Furan, being an electron-rich aromatic compound, can undergo a Diels-Alder reaction with electron-deficient alkenes like trans-1,2-dicyanoethylene. The cyano groups make the alkene highly electrophilic, favoring cycloaddition.

Step 3: Predict the mechanism. In the Diels-Alder reaction, the π-electrons of furan interact with the π-electrons of the alkene to form a new six-membered ring. This reaction proceeds via a concerted mechanism, where bonds are formed simultaneously.

Step 4: Determine the stereochemistry. Since the alkene is trans, the substituents (cyano groups) will retain their relative trans configuration in the product. The newly formed six-membered ring will have the cyano groups positioned opposite to each other.

Step 5: Draw the product structure. The product will be a bicyclic compound where the furan and alkene have combined to form a six-membered ring fused to the original furan ring. The cyano groups will be attached to the new ring in a trans configuration.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, resulting in the formation of a new bond. In this case, furan, which contains a nucleophilic double bond, can react with the electrophilic trans-1,2-dicyanoethylene. Understanding this mechanism is crucial for predicting the products of the reaction.

Aromaticity and Reactivity

Furan is an aromatic compound, which means it has a cyclic structure with delocalized π electrons that contribute to its stability. However, furan is more reactive than benzene due to the presence of an oxygen atom in the ring, which can influence its reactivity towards electrophiles. Recognizing the balance between aromatic stability and reactivity is essential for predicting the outcome of the reaction.

Diels-Alder Reaction

The Diels-Alder reaction is a [4+2] cycloaddition reaction between a diene and a dienophile, leading to the formation of a six-membered ring. In this scenario, furan acts as the diene, while trans-1,2-dicyanoethylene serves as the dienophile. Familiarity with this reaction type is vital for understanding how the products are formed from the reactants in the given question.

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