Predict the major, organic product for the following reaction. <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch22_Q10_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains one reactant. The reactant has the following structure: A 1 O and 6 C heteronuclear alkene chain is depicted as a line structure using 6 lines bent in the form of an incomplete hexagon. O occupies the fourth position. A double bond is present between C 1 and C 2 and C 4 and C 5. C 1 is single bonded to C H 3 on the lower right in the form of a line. C 3 is wedge bonded to C H 3 on the lower left in the form of a wedged line. C 5 is single bonded to C H 3 on the upper right in the form of a line. Delta is written under the reaction arrow." />

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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

Claisen Rearrangement

Organic Chemistry

16. Conjugated Systems

Claisen Rearrangement

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Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a molecule. A 4-carbon alkane chain is depicted as a line structure using 3 zigzag lines. C 2 is double bonded to O above. C 4 is dash bonded to C H 3 on the lower right in the form of a dashed line. C 4 is single bonded above to C 3 of a 3-carbon alkene chain depicted as a line structure using 2 zigzag lines. In the alkene chain, a double bond is present between C 1 and C 2. C 3 of the alkene chain is single bonded to C H 3 on the right and C H 3 on the upper right, each in the form of a line.

The figure illustrates the structure of a molecule. A 4-carbon alkene chain is depicted as a line structure using 3 zigzag lines. A double bond is present between C 2 and C 3. C 4 is wedge bonded to C H 3 on the lower right in the form of a wedged line. C 4 is single bonded above to C 2 of a 2-carbon alkane chain depicted as a line structure using 1 line. C 1 of the alkane chain is double bonded to O above and single bonded to H on the lower left. C 2 of the 2-carbon alkane chain is single bonded to C H 3 on the right and C H 3 on the upper right, each in the form of a line.

The figure illustrates the structure of a molecule. A 6-carbon alkene chain is depicted as a line structure using 5 lines bent in the form of an incomplete hexagon. A double bond is present between C 4 and C 5. C 1 is double bonded to O above and single bonded to H on the lower left. C 2 is single bonded to C H 3 on the right and C H 3 on the upper right, each in the form of a line. C 3 is dash bonded to C H 3 on the lower right in the form of a dashed line.

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Verified step by step guidance

Identify the starting material as a 2,5-dimethylfuran, which is a heterocyclic compound containing an oxygen atom in a five-membered ring with two double bonds.

Recognize that the reaction involves heating (indicated by the delta symbol), which suggests a pericyclic reaction such as a Diels-Alder reaction.

In a Diels-Alder reaction, a diene (the furan ring in this case) reacts with a dienophile. Here, the furan acts as the diene, and the reaction is likely intramolecular, forming a new six-membered ring.

Predict the formation of a bicyclic compound where the furan ring opens up and forms a new six-membered ring with the existing substituents rearranging.

Consider the stereochemistry of the product, as the Diels-Alder reaction is stereospecific, leading to the formation of a specific stereoisomer of the bicyclic compound.