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_Q11_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains three reactants. The first reactant has the following structure: A 6-carbon hexagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 5 and C 6 are each wedge bonded to a common O atom on the left. The second reactant written over the reaction arrow has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is single bonded to C u L i. The pentagonal ring is enclosed within brackets with subscript 2. The third reactant is H 3 O superscript plus quench 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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a molecule labeled only stereoisomer. A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is dash bonded to C 5 of a 6-carbon hexagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 6 of the 6-carbon ring is wedge bonded to O H.

The figure illustrates the structure of a molecule labeled meso and achiral. A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is dash bonded to C 5 of a 6-carbon hexagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 6 of the 6-carbon ring is wedge bonded to O H.

The figure illustrates the structures of two molecules labeled enantiomers. The first molecule has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is dash bonded to C 5 of a 6-carbon hexagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 6 of the 6-carbon ring is wedge bonded to O H. The second molecule has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is wedge bonded to C 5 of a 6-carbon hexagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 6 of the 6-carbon ring is dash bonded to O H.

The figure illustrates the structures of two molecules labeled diastereomers. The first molecule has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is dash bonded to C 5 of a 6-carbon hexagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 6 of the 6-carbon ring is wedge bonded to O H.The second molecule has the following structure: A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is dash bonded to C 5 of a 6-carbon hexagonal ring in a vertical orientation with C 1 occupying the topmost vertex. C 6 of the 6-carbon ring is dash bonded to O H.

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Verified step by step guidance

Identify the starting material: The starting material is an epoxide, which is a three-membered cyclic ether. Epoxides are highly reactive due to the ring strain.

Recognize the reagent: The reagent is a Gilman reagent, specifically a dialkylcuprate (R2CuLi). Gilman reagents are known for their ability to open epoxide rings through nucleophilic attack.

Determine the site of attack: The Gilman reagent will attack the less hindered carbon of the epoxide ring, leading to ring opening. This is due to the nucleophilic nature of the reagent, which prefers less sterically hindered sites.

Consider stereochemistry: The attack by the Gilman reagent will result in inversion of configuration at the site of attack due to the backside attack mechanism typical of SN2 reactions.

Account for the quenching step: The second step involves quenching with H3O+, which will protonate the alkoxide intermediate formed after the ring opening, resulting in an alcohol group in the final product.