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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4:01 minutes

Problem 106

Textbook Question

While attempting to recrystallize maleic anhydride, a student dissolved it in freshly distilled cyclopentadiene rather than in freshly distilled cyclopentane. Was her recrystallization successful?

Verified step by step guidance

Step 1: Understand the chemical properties of maleic anhydride and cyclopentadiene. Maleic anhydride is a reactive compound that can undergo Diels-Alder reactions with dienes, such as cyclopentadiene, due to its electron-deficient double bond.

Step 2: Analyze the solvent choice. Cyclopentadiene is a conjugated diene, meaning it has alternating double bonds that make it highly reactive in Diels-Alder reactions. Cyclopentane, on the other hand, is a saturated hydrocarbon and would not react with maleic anhydride.

Step 3: Consider the reaction between maleic anhydride and cyclopentadiene. When maleic anhydride is dissolved in cyclopentadiene, a Diels-Alder reaction is likely to occur, forming a new cyclic compound rather than allowing maleic anhydride to recrystallize.

Step 4: Evaluate the recrystallization process. Recrystallization requires the solute (maleic anhydride) to dissolve in a solvent and then precipitate out in a purer form upon cooling. If a chemical reaction occurs instead, recrystallization cannot be successful.

Step 5: Conclude based on the chemical interaction. Since maleic anhydride reacts with cyclopentadiene to form a Diels-Alder adduct, the recrystallization attempt was not successful. The student inadvertently caused a chemical reaction rather than recrystallization.

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Key Concepts

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

Recrystallization

Recrystallization is a purification technique used to separate a desired compound from impurities based on differences in solubility. The process involves dissolving the compound in a suitable solvent at high temperatures and then allowing it to crystallize as the solution cools. The choice of solvent is crucial, as it must dissolve the compound when hot but not when cold, ensuring that impurities remain in solution.

Diels-Alder Reaction

The Diels-Alder reaction is a cycloaddition reaction between a conjugated diene and a dienophile, resulting in the formation of a six-membered ring. In this case, cyclopentadiene acts as the diene, and maleic anhydride can serve as the dienophile. If cyclopentadiene is used instead of cyclopentane, it may lead to an unexpected reaction, potentially forming a bridged product rather than allowing for successful recrystallization.

Solvent Effects on Recrystallization

The choice of solvent significantly impacts the recrystallization process. Cyclopentadiene, being a reactive diene, can participate in chemical reactions, whereas cyclopentane is inert and would not interfere with the recrystallization of maleic anhydride. Using cyclopentadiene instead of cyclopentane may lead to the formation of new products rather than pure maleic anhydride crystals, indicating that the recrystallization was likely unsuccessful.

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Related Practice

Textbook Question

Recall (Section 16-10) that two positions of anthracene sometimes react more like polyenes than like aromatic compounds.

b. The Diels–Alder reaction of anthracene with maleic anhydride is a common organic lab experiment. Predict the product of this Diels–Alder reaction.

Textbook Question

Show the product of the Diels–Alder dimerization of cyclobutadiene. (This reaction is similar to the dimerization of cyclopentadiene, discussed in Section 15-11.)

Textbook Question

Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reaction takes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of the product isomerizes to the exo isomer at 90 °C.

c. Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetically controlled or one that is thermodynamically controlled, or both.

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

What are the products of the following reactions?

Textbook Question

What are the products of the following reactions?

Textbook Question

Predict the products of the following proposed Diels–Alder reactions.

(e)

Textbook Question

Predict the products of the following proposed Diels–Alder reactions.

(d)