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/Ch16_Q12_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains two reactants. The first reactant has the following structure: A 5-carbon pentagonal ring is in a horizontal orientation with C 1 occupying the leftmost vertex. C 3 is wedge bonded to C 1 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 2 and C 3. C 4 is wedge bonded to C 1 of a second 3-carbon alkene chain depicted as a line structure using 2 zigzag lines. In the second alkene chain, a double bond is present between C 2 and C 3. The second reactant written over the reaction arrow has the following structure: L subscript n R u, double bond, C H 2." />

Table of contents

Skip topic navigation

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

35. Transition Metals

Cross-Coupling General Reactions

Organic Chemistry

35. Transition Metals

Cross-Coupling General Reactions

Previous problemNext problem

Struggling with Organic Chemistry?

Join thousands of students who trust us to help them ace their exams!Watch the first video

Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a molecule labeled meso and achiral. A 5-carbon pentagonal ring is in a horizontal orientation with C 1 occupying the leftmost vertex. C 3 is wedge bonded to C 1 of a 4-carbon alkene chain depicted as a line structure using 3 lines bent in the shape of an incomplete vertically oriented hexagon. There is a double bond betwen C 2 and C3. C 4 of the ring is wedge bonded to C 4 of the alkene chain.

The figure illustrates the structure of a molecule. A 5-carbon pentagonal ring is in a horizontal orientation with C 1 occupying the leftmost vertex. C 3 is wedge bonded to C 1 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 2 and C 3. C 4 is wedge bonded to C 1 of a 4-carbon alkene chain depicted as a line structure using 3 zigzag lines. In the 4-carbon alkene chain, a double bond is present between C 2 and C 3. C 4 of the 4-carbon alkene chain is wedge bonded on the lower right to C 4 of a second 5-carbon pentagonal ring in a horizontal orientation with C 1 occupying the rightmost vertex. C 3 of the second 5-carbon ring is wedge bonded to C 3 of a second 3-carbon alkene chain depicted as a line structure using 2 zigzag lines. In the second 3-carbon alkene chain, a double bond is present between C 1 and C 2.

Previous problemNext problem

Verified step by step guidance

Identify the reaction type: The presence of LnRu=CH2 suggests a metathesis reaction, specifically an olefin metathesis, which involves the redistribution of alkene fragments.

Analyze the starting material: The compound is a bicyclic structure with two terminal alkenes. This setup is ideal for ring-closing metathesis (RCM), which can form a new ring by connecting the two alkene ends.

Consider the possible products: The reaction can lead to different ring sizes depending on which alkenes participate in the metathesis. The most likely product is the one that forms the most stable ring, often a five or six-membered ring.

Evaluate the stability and symmetry: The images provided show meso and achiral products, indicating that the reaction favors symmetrical and stable structures. This suggests that the reaction will likely form a product with these characteristics.

Predict the major product: Based on the stability and symmetry considerations, the major product is likely to be a meso and achiral compound, possibly forming a new ring that maintains these properties.