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/Ch28_Q11_QT.jpg" alt="The figure illustrates a reaction in which the answer has to be determined. The reaction proceeds with two pathways. The first pathway contains two reactants. The first reactant, a bridged bicyclic compound, has the following structure: A 6-carbon non-planar cyclic carbon ring is shown. C 1 is single bonded to C 2 below and toward the observer. C 2 is single bonded to C 3 on the upper left. C 3 is single bonded to C 4 on the lower left. C 4 is single bonded to C 5 above and away from the observer. C 5 is single bonded to C 6 on the upper right and away from the observer. C 6 is single bonded to C 1 on the lower right, completing the ring. C 3 and C 6 are each single bonded to C 7 above the ring. A double bond is present between C 4 and C 5. The second reactant written over the reaction arrow has the following structure: L subscript n R u, double bond, C H 2. The second pathway contains two reactants. The first reactant has the following structure: A 3-carbon alkane chain is depicted as a line structure using 2 zigzag lines. C 1 is single bonded to O H on the upper left. C 2 is double bonded to C H 2 above in the form of 2 parallel lines. C 3 is single bonded to O H on the upper right. The second reactant written over the reaction arrow has the following structure: A central C atom is double bonded to O above and is single bonded to C l on the lower right and C l on the lower left. The products of the two pathways react with a second molecule of the second reactant of the first pathway that has the following structure: L subscript n R u, double bond, C H 2." />

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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

35. Transition Metals

Cross-Coupling General Reactions

Organic Chemistry

35. Transition Metals

Cross-Coupling General Reactions

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Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a complex polymer. A 4 O and 8 C heteronuclear alkane chain is depicted as a line structure using 11 zigzag lines. The first O atom occupies the fourth position. The second O atom occupies the sixth position. The third O atom occupies the tenth position. The fourth O atom occupies the twelfth position. C 4 and C 8 are each double bonded to O above. The heteronuclear alkane chain is enclosed within square brackets with subscript n. C 2 is double bonded below to C H in the form of two parallel lines. C H is single bonded on the lower right to C 2 of a 5-carbon pentagonal ring in a horizontal orientation with C 1 occupying the leftmost vertex. C 5 of the pentagonal ring is single bonded to a second C H group in the form of a line. The C H group at C 2 of the 5-carbon ring, the 5-carbon ring, and the C H group at C 5 of the 5-carbon ring are enclosed within square brackets with subscript n. The C H group at C 5 of the 5-carbon ring is double bonded below to C 2 of a second 4 O and 8 C heteronuclear alkane chain depicted as a line structure using 11 zigzag lines. In the second heteronuclear alkane chain, the first O atom occupies the fourth position, the second O atom occupies the sixth position, the third O atom occupies the tenth position, and the fourth O atom occupies the twelfth position. C 4 and C 8 of the second heteronuclear alkane chain are each double bonded to O below. C 6 of the first heteronuclear alkane chain is double bonded below to a third C H group in the form of two parallel lines. The third C H group is single bonded on the lower right to C 2 of a second 5-carbon pentagonal ring in a horizontal orientation with C 1 occupying the leftmost vertex. C 5 of the second pentagonal ring is single bonded to a fourth C H group in the form of a line. The C H group at C 2 of the second 5-carbon ring, the second 5-carbon ring, and the C H group at C 5 of the second 5-carbon ring are enclosed within square brackets with subscript n. The C H group at C 5 of the second 5-carbon ring is double bonded below to C 6 of the second heteronuclear alkane chain. The second heteronuclear alkane chain is enclosed within square brackets with subscript n. C 1 of each heteronuclear alkane chain has an open single bond on the left extending beyond the left square bracket. The fourth O atom of each heteronuclear alkane chain has an open single bond on the right extending beyond the right square bracket.

The figure illustrates the structure of a polymer. A 4 O and 8 C heteronuclear alkane chain is depicted as a line structure using 11 zigzag lines. The first O atom occupies the fourth position, the second O atom occupies the sixth position, the third O atom occupies the tenth position, and the fourth O atom occupies the twelfth position. C 4 and C 8 are each double bonded to O below. C 2 is double bonded to C H above in the form of 2 parallel lines. C H is single bonded on the upper right to C 2 of a 5-carbon pentagonal ring in a vertical orientation with C 1 occupying the bottommost vertex. C 6 of the heteronuclear alkane chain is double bonded to a second C H group above in the form of 2 parallel lines. The second C H group is single bonded on the upper left to C 5 of the 5-carbon pentagonal ring in a vertical orientation with C 1 occupying the bottommost vertex. The entire structure is enclosed within square brackets with subscript n. C 1 of the heteronuclear alkane chain has an open single bond on the left extending beyond the left square bracket. The fourth O atom of the heteronuclear alkane chain has an open single bond on the right extending beyond the right square bracket.

The figure illustrates the structure of a polymer. A 3 O and 6 C heteronuclear alkene chain is depicted as a line structure using 8 zigzag lines. The first O atom occupies the first position. The second O atom occupies the fifth position. The third O atom occupies the seventh position. A double bond is present between C 5 and C 6. C 2 is double bonded to C H 2 above in the form of two parallel lines. C 4 is double bonded to O below. C 6 is single bonded on the lower right to C 5 of a 5-carbon pentagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 2 of the ring is single bonded to a C H group in the form of a line. The entire structure is enclosed within square brackets with subscript n. A single bond from the first O atom extends across the left bracket. A double bond from the C H group at C 2 of the 5-carbon ring extends across the right bracket.

The figure illustrates the structure of a polymer. A 2 O and 4 C heteronuclear alkane chain is depicted as a line structure using 5 zigzag lines. The first O atom occupies the first position, and the second O atom occupies the fifth position. C 2 is double bonded to C H 2 above in the form of two parallel lines. C 4 is double bonded to O below. The heteronuclear alkane chain is enclosed within square brackets with subscript n. The first O atom has an open single bond on the left extending beyond the left square bracket. C 4 is single bonded to a second O atom on the upper right. The second O atom is single bonded on the lower right to C 1 of a 2-carbon alkene chain depicted as a line structure using 2 parallel lines. C 2 of the alkene chain is single bonded on the lower right to C 5 of a 5-carbon pentagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 2 of the 5-carbon ring is single bonded to a C H group in the form of a line. The pentagonal ring along with the C H group is enclosed within square brackets with subscript n. The C H group has an open double bond on the right extending beyond the right square bracket.

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Verified step by step guidance

Identify the reactants and reagents in the reaction. The reactants include a bicyclic compound and a diol with a double bond. The reagents are a Grubbs catalyst (LnRu=CH2) and a diacid chloride.

Recognize the type of reaction. The presence of the Grubbs catalyst suggests a metathesis reaction, likely a ring-opening metathesis polymerization (ROMP) or a cross-metathesis.

Consider the role of the diacid chloride. It can react with the diol to form an ester linkage, potentially leading to polymerization.

Analyze the structure of the potential polymer. The bicyclic compound can undergo ring-opening, and the diol can form ester linkages with the diacid chloride, resulting in a polymer with repeating units.

Predict the major product. The major product is likely a polymer formed by the combination of the bicyclic compound and the diol, with ester linkages introduced by the diacid chloride, facilitated by the Grubbs catalyst.