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/Ch17_Q05_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 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 2 is double bonded to O above. The second reactant written over the reaction arrow has the following structure: A 4-carbon alkane chain is depicted as a line structure using 3 zigzag lines. C 2 is single bonded to C H 3 below in the form of a line. C 4 is single bonded to L i on the upper right. The third reactant is H 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 plus or minus. A 9-carbon alkane chain is depicted as a line structure using 8 zigzag lines. C 2 is single bonded to C H 3 below in the form of a line. C 6 is wedge bonded to O H below.

The figure illustrates the structure of a molecule labeled plus or minus. An 8-carbon alkane chain is depicted as a line structure using 7 zigzag lines. C 2 is single bonded to C H 3 below in the form of a line. C 5 is wedge bonded to O H above.

The figure illustrates the structure of a molecule labeled plus or minus. A 7-carbon alkane chain is depicted as a line structure using 6 zigzag lines. C 2 is single bonded to C H 3 below in the form of a line. C 4 is wedge bonded to O H on the lower left and 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 reactants: The starting material is a ketone, specifically 2-pentanone, and the reagent is an organolithium compound, 2-lithiopentane.

Understand the reaction type: This is a nucleophilic addition reaction where the organolithium reagent acts as a nucleophile, attacking the electrophilic carbonyl carbon of the ketone.

Predict the intermediate: The nucleophilic attack by the organolithium reagent will form a new carbon-carbon bond, resulting in an alkoxide intermediate.

Consider the quenching step: The alkoxide intermediate is then protonated by the acid (H⁺ quench) to form the corresponding alcohol.

Determine the stereochemistry: Since the reaction involves the formation of a new chiral center, the product will be a racemic mixture, indicated by the (±) symbol in the product structures.