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

Previous problemNext problem

4:16 minutes

Problem 25i

Textbook Question

Predict the products of the following reactions.
(i)

Verified step by step guidance

Step 1: Identify the reactants. The first reactant is furan, a five-membered aromatic ring containing an oxygen atom. The second reactant is a molecule with two aldehyde groups (-CHO) attached to a central alkyne (-C≡C-).

Step 2: Recognize the type of reaction. This reaction is likely a Diels-Alder reaction, where a conjugated diene (furan) reacts with a dienophile (the molecule containing the alkyne and aldehyde groups). The Diels-Alder reaction forms a six-membered ring by a [4+2] cycloaddition mechanism.

Step 3: Analyze the electron-withdrawing groups on the dienophile. The aldehyde groups (-CHO) are electron-withdrawing, which makes the alkyne more reactive as a dienophile. This enhances the likelihood of the cycloaddition reaction.

Step 4: Predict the product structure. The furan will act as the diene, and the alkyne will act as the dienophile. The reaction will form a new six-membered ring, incorporating the oxygen atom from furan and the carbon atoms from the alkyne. The aldehyde groups will remain attached to the newly formed ring.

Step 5: Consider stereochemistry. The Diels-Alder reaction typically proceeds with stereospecificity, meaning the relative orientation of substituents in the product will depend on the approach of the reactants. The aldehyde groups will likely end up in a cis configuration due to the concerted nature of the reaction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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.

Electrophilicity of Dienophiles

Dienophiles are typically electron-deficient alkenes or alkynes that react with electron-rich dienes in the Diels-Alder reaction. The presence of electron-withdrawing groups, such as carbonyls (C=O), enhances the electrophilicity of the dienophile, making it more reactive towards the diene.

Stereochemistry of Products

The stereochemistry of the products formed in the Diels-Alder reaction is crucial, as the reaction is stereospecific. The relative orientation of substituents on the diene and dienophile is preserved in the product, leading to specific stereochemical outcomes that can influence the properties and reactivity of the resulting compound.

Watch next

Master Bridged-Products with a bite sized video explanation from Johnny

Start learning