Which of the following will successfully synthesize the given target? <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch24_Q10_QT.jpg" alt="The figure illustrates a reaction. The reaction contains one reactant and one product. The reactant has the following structure: A 4-carbon alkane chain is depicted as a line structure using 3 zigzag lines. C 1 is single bonded to O H on the upper left. C 4 is double bonded to O above and single bonded to 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 2 is single bonded to C H 3 above and C H 3 on the upper left, each in the form of a line. C 4 is single bonded to O H above. C 5 is single bonded below to C 2 of a 2-carbon alkane chain depicted as a line structure using 1 line. C 1 of the 2-carbon alkane chain is single bonded to O H below. C 6 is double bonded to O above and single bonded to H on the lower right." />

Table of contents

Skip topic navigation

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

Aldol Condensation

Organic Chemistry

25. Condensation Chemistry

Aldol Condensation

Previous problemNext problem

Struggling with Organic Chemistry?

Join thousands of students who trust us to help them ace their exams!Watch the first video

Multiple Choice

Which of the following will successfully synthesize the given target?

The figure illustrates a series of three reactions to synthesize the target product. The first reaction contains two species. The first species is E t 3 S i C l written over the reaction arrow. The second species is E t 3 N written under the reaction arrow.The second reaction contains three species. The first species is L D A written over the reaction arrow. The second species written under 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 on the upper left and C H 3 above, each in the form of a line. C 4 is double bonded to O above and single bonded to H on the lower right. The third species is H superscript plus quench written under the reaction arrow.The third reaction contains one species. The species is H 2 written over the reaction arrow. P d over C is written under the reaction arrow.

Previous problemNext problem

Verified step by step guidance

Examine the target molecule and identify the functional groups present. The target molecule contains multiple hydroxyl groups and a ketone group.

Consider the starting material, which is a carboxylic acid. The transformation involves converting the carboxylic acid into a ketone and adding hydroxyl groups.

Analyze the first reaction sequence: Et3SiCl with Et3N. This is typically used for silyl protection of alcohols, which is not directly relevant to the transformation needed.

Evaluate the second reaction sequence: H2SO4 followed by NaOH, H2O. This sequence suggests an aldol condensation, which could form the carbon skeleton needed for the target molecule.

Consider the third reaction sequence: NaH followed by PhCH2Br. This involves alkylation, which does not directly lead to the target structure. The presence of LDA and Pd/C suggests enolate formation and hydrogenation, which are not directly applicable here.