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_Q06_QT.jpg" alt="The figure illustrates a reaction in which the product has to be determined. The reaction contains two 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 a central C atom in the form of a line. The central C atom is double bonded to O above and single bonded to H on the lower right. 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 5 is single bonded to C 2 of a 2-carbon alkane chain depicted as a line structure using 1 line. C 1 of the alkane chain is double bonded to P P h 3 on the upper left. C 2 of the alkane chain is double bonded to O above." />

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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

21. Aldehydes and Ketones: Nucleophilic Addition

Wittig Reaction

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Wittig Reaction

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Multiple Choice

Predict the major, organic product for the following reaction.

The figure illustrates the structure of a molecule labeled achiral. 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 3-carbon alkene chain depicted as a line structure using 2 zigzag lines. In the alkene chain, a double bond is present between C 1 and C 2. C 3 of the alkene chain is double bonded to O above and single bonded on the lower right to C 5 of a second 5-carbon pentagonal ring in a vertical orientation with C 1 occupying the topmost vertex.

The figure illustrates the structure of a molecule labeled plus or minus. 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 3-carbon alkane chain depicted as a line structure using 2 zigzag lines. C 1 of the alkane chain is wedge bonded to O H above. C 3 of the alkene chain is double bonded to O above. C 3 of the alkene chain is single bonded on the lower right to C 5 of a second 5-carbon pentagonal ring in a vertical orientation with C 1 occupying the topmost vertex.

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Verified step by step guidance

Identify the reaction type: The presence of Ph₃P indicates a Wittig reaction, which is used to convert aldehydes or ketones into alkenes.

Analyze the reactants: The starting material is an aldehyde with a cyclopentanone group. The Wittig reagent is a phosphonium ylide, which will react with the aldehyde.

Understand the mechanism: The Wittig reaction involves the formation of a betaine intermediate, followed by the formation of an oxaphosphetane, which then decomposes to form the alkene product.

Predict the product: The major product of a Wittig reaction is typically an alkene formed by replacing the carbonyl group with a double bond between the carbon of the aldehyde and the carbon of the ylide.

Consider stereochemistry: Wittig reactions can lead to E/Z isomers, but in this case, the product is achiral, indicating no stereocenters are formed in the major product.