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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4:02 minutes

Problem 14f

Textbook Question

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

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Step 1: Identify the components of the Diels–Alder reaction. The reaction involves a conjugated diene (CH3O-substituted diene) and a dienophile (cyano-substituted alkene). The diene has two double bonds in conjugation, and the dienophile has electron-withdrawing cyano groups that enhance its reactivity.

Step 2: Analyze the electron flow in the reaction. The Diels–Alder reaction is a [4+2] cycloaddition, where the diene contributes four π-electrons and the dienophile contributes two π-electrons. The reaction proceeds via a concerted mechanism, forming a six-membered ring.

Step 3: Determine the regiochemistry of the reaction. The electron-donating methoxy group (-OCH3) on the diene will direct the reaction due to its electronic effects. The cyano groups (-CN) on the dienophile are electron-withdrawing, influencing the orientation of the addition. The most stable product will result from the alignment of these groups to minimize steric hindrance and maximize electronic compatibility.

Step 4: Predict the stereochemistry of the product. The Diels–Alder reaction is stereospecific, meaning that the stereochemistry of the diene and dienophile is preserved in the product. If the diene and dienophile are planar, the product will have cis substituents on the newly formed six-membered ring.

Step 5: Draw the product structure. Combine the diene and dienophile to form a six-membered ring. The methoxy group (-OCH3) and cyano groups (-CN) will be positioned based on the regio- and stereochemical considerations discussed. Ensure the product reflects the correct connectivity and stereochemistry.

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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 chemists.

Diene and Dienophile

In the context of the Diels–Alder reaction, a diene is a molecule containing two double bonds that can participate in the reaction, while a dienophile is a compound that contains a double or triple bond and reacts with the diene. The electronic and steric properties of both the diene and dienophile significantly influence the reaction's outcome, including product formation and selectivity.

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 product. 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 products of the reaction.

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Textbook Question

Predict the product of the following reactions. [When all of the reactions from this chapter are shown together, you must first decide which type of reaction each is. Is it a Diels–Alder, an electrocyclic, or a sigmatropic rearrangement? Drawing the product will be easier once this determination is made.]

(a)

Textbook Question

Show the steps involved in the following reaction:

Textbook Question

Predict the products of the following proposed Diels–Alder reactions. Include stereochemistry where appropriate.

(e)

(f)

Textbook Question

An important variation of the Diels–Alder reaction is intramolecular, in which the diene and the dienophile are connected. This type of Diels–Alder reaction makes two new rings. Draw the compound produced in each of these examples; try to predict stereochemistry (using models will help). In some cases, Lewis acid catalysts are used; that can be ignored for this problem.

(a)

(b)

Textbook Question

What stereochemical result would you expect if the Diels–Alder reaction with the free α,β- unsaturated ketone was faster than reaction with the iminium-bound alkene?

Textbook Question

We predicted that the products would have a 1,2- or 1,4-relationship of the proper substituents. Draw the charge-separated resonance forms of the reactants to support these predictions.

(a) (b)

Textbook Question

(c)

Textbook Question

(d)

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