Which of the following syntheses will NOT form the given target? <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch19_Q14_QT.jpg" alt="The figure illustrates a reaction. The reaction contains one reactant and one product. The reactant has the following structure: A 3-carbon alkane chain is depicted as a line structure using 2 zigzag lines. C 3 is single bonded to O H on the lower right. The product has the following structure: A 6-carbon alkane chain is depicted as a line structure using 5 zigzag lines. C 3 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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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Multiple Choice

Which of the following syntheses will NOT form the given target?

The figure illustrates the species used to synthesize the desired target product in three stjpg. The first step contains two species. The first species is S O C l 2 written over the reaction arrow. The second species is N E t 3 written under the reaction arrow.The second step contains two species. The first species is N a C N written over the reaction arrow. The second species is T H F written under the reaction arrow.The third step contains two species. The first species written over the reaction arrow has the following structure: A 2-carbon alkane chain is depicted as a line structure using 1 line. C 2 is single bonded to M g B r on the upper right. The second species is H superscript plus quench written under the reaction arrow.

The figure illustrates the species used to synthesize the desired target product in three stjpg. The first step contains one species. The species is P B r 3 written over the reaction arrow.The second step contains two species. The first species is N a C N written over the reaction arrow. The second species is T H F written under the reaction arrow.The third step contains two species. The first species 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 3 is single bonded to M g B r on the upper right. The second species is H superscript plus quench written under the reaction arrow.

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Identify the target molecule as a ketone, specifically 2-pentanone, which can be formed from the oxidation of a secondary alcohol or through other synthetic routes.

Examine the first synthesis: The alcohol is converted to an alkyl chloride using SOCl2, then to a nitrile with NaCN, followed by a Grignard reaction with propylmagnesium bromide. This sequence does not lead to the target ketone.

Examine the second synthesis: The alcohol is oxidized to a carboxylic acid using H2CrO4, converted to an acyl chloride with SOCl2, and then reacted with a Gilman reagent. This sequence can form the target ketone.

Examine the third synthesis: The alcohol is converted to an alkyl bromide using PBr3, then to a nitrile with NaCN, followed by a Grignard reaction with propylmagnesium bromide. This sequence does not lead to the target ketone.

Examine the fourth synthesis: The alcohol is oxidized to an aldehyde using PCC, followed by a Grignard reaction with propylmagnesium bromide, and then oxidized again with PCC. This sequence can form the target ketone.