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_Q04_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 pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is single bonded to C H 2 in the form of a line. C H 2 is single bonded to L i on the lower right. The second reactant written over the reaction arrow 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 H on the lower left and double bonded to O above. C 2 is single bonded to C H 3 below in the form of a line. 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. A 5-carbon pentagonal ring is in a vertical orientation with C 1 occupying the topmost vertex. C 2 is single bonded to C 1 of a 4-carbon alkane chain depicted as a line structure using 3 zigzag lines. C 2 of the alkane chain is double bonded to O below. C 3 of the alkane chain is single bonded to C H 3 above in the form of a line.

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Verified step by step guidance

Identify the reactants: The reaction involves an organolithium compound (cyclopentyl lithium) and an aldehyde (isobutyraldehyde).

Understand the reaction type: This is a nucleophilic addition reaction where the organolithium compound acts as a nucleophile and attacks the electrophilic carbonyl carbon of the aldehyde.

Predict the nucleophilic attack: The carbon attached to lithium in the cyclopentyl lithium will attack the carbonyl carbon of the aldehyde, breaking the C=O double bond and forming a new C-C bond.

Consider the intermediate: The result of the nucleophilic attack is an alkoxide intermediate, where the oxygen from the carbonyl group now bears a negative charge.

Protonation step: The alkoxide intermediate is then protonated by the addition of H3O+ (acidic workup), resulting in the formation of the corresponding alcohol as the final product.