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/Ch21_Q10_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 horizontal orientation with C 1 occupying the leftmost vertex. C 4 is double bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 2 of the alkane chain is double bonded to O above. The second reactant is P h 2 C u L i written over the reaction arrow. 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

25. Condensation Chemistry

Conjugate Addition

Organic Chemistry

25. Condensation Chemistry

Conjugate Addition

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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 5-carbon pentagonal ring is in a horizontal orientation with C 1 occupying the leftmost vertex. C 4 is double bonded to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 2 of the alkane chain is wedge bonded to P h on the upper left and dash bonded to O H on the upper right.

The figure illustrates the structure of a molecule labeled achiral. A 5-carbon pentagonal ring is in a horizontal orientation with C 1 occupying the rightmost vertex. C 1 is single bonded to P h on the upper right and single bonded on the lower right to C 1 of a 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 2 of the alkane chain is double bonded to O above.

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Verified step by step guidance

Identify the type of reaction: The reaction involves a conjugate addition (1,4-addition) of a Gilman reagent (Ph2CuLi) to an α,β-unsaturated ketone.

Recognize the role of the reagents: Ph2CuLi is a lithium diorganocuprate, which is known for performing 1,4-additions to α,β-unsaturated carbonyl compounds.

Determine the site of addition: In a 1,4-addition, the nucleophile (Ph group from Ph2CuLi) will add to the β-carbon of the α,β-unsaturated ketone, resulting in the formation of a new carbon-carbon bond.

Consider the stereochemistry: The addition of the Ph group to the β-carbon can lead to the formation of a chiral center. However, since the product is achiral, the stereochemistry is not a concern in this case.

Complete the reaction with a protonation step: After the addition of the Ph group, the enolate intermediate is protonated by the H⁺ quench, resulting in the final product, which is an achiral ketone with a phenyl group added to the β-position.