Which of the follosing is the best synthesis of the given molecule? <img src="https://media.pearsoncmg.com/ph/esm/ecs_mullins_organic1e/msa/content/practice-test/img/Ch13_Q14_QT.jpg" alt="The figure illustrates the structure of a molecule. A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 4-carbon alkane chain depicted as a line structure using 3 zigzag lines. C 1 of the alkane chain is wedge bonded to O H above. C 3 of the alkane chain is single bonded to C H 3 on the upper left in the form of a line and C l on the upper 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

12. Alcohols, Ethers, Epoxides and Thiols

Silyl Ether Protecting Groups

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Silyl Ether Protecting Groups

Next 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 follosing is the best synthesis of the given molecule?

The figure illustrates a series of three reactions to obtain a given product. The first reaction contains three reactants. The first reactant has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 4-carbon alkene chain depicted as a line structure using 3 zigzag lines. In the alkene chain, a double bond is present between C 3 and C 4. C 1 of the alkene chain is wedge bonded to O H above. C 3 of the alkene chain is single bonded to C H 3 above in the form of a line. The second reactant is E t 3 S i C l written over the reaction arrow. The third reactant is E t 3 N written under the reaction arrow.The second reaction contains one reactant. The reactant is H C l written over the reaction arrow.The third reaction contains two reactants. The first reactant is B u 4 N F written over the reaction arrow. The second reactant is H 2 O written under the reaction arrow.

The figure illustrates a series of three reactions to obtain a given product. The first reaction contains two reactants. The first reactant has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 4-carbon alkene chain depicted as a line structure using 3 zigzag lines. In the alkene chain, a double bond is present between C 3 and C 4. C 1 of the alkene chain is wedge bonded to O H above. C 3 of the alkene chain is single bonded to C H 3 above in the form of a line. The second reactant is H C l written over the reaction arrow.The second reaction contains two reactants. The first reactant is E t 3 S i C l written over the reaction arrow. The second reactant is E t 3 N written under the reaction arrow.The third reaction contains two reactants. The first reactant is B u 4 N F written over the reaction arrow. The second reactant is H 2 O written under the reaction arrow.

The figure illustrates a reaction. The reaction contains two reactants. The first reactant has the following structure: A benzene ring is in a vertical orientation with C 1 occupying the topmost vertex. The ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 2 is single bonded to C 1 of a 4-carbon alkene chain depicted as a line structure using 3 zigzag lines. In the alkene chain, a double bond is present between C 3 and C 4. C 1 of the alkene chain is wedge bonded to O H above. C 3 of the alkene chain is single bonded to C H 3 above in the form of a line. The second reactant is H C l written over the reaction arrow.

Next problem

Verified step by step guidance

Identify the target molecule: The target molecule is a secondary alcohol with a phenyl group and a chloro group on adjacent carbon atoms.

Analyze the first synthesis route: The first image shows a reaction sequence starting with a triethylsilyl chloride (Et3SiCl) protection of the alcohol, followed by HCl treatment, and then deprotection with Bu4NF. This sequence is likely to protect the alcohol, introduce the chloro group, and then deprotect the alcohol.

Analyze the second synthesis route: The second image shows a similar sequence but starts with HCl treatment, which might lead to the formation of a carbocation and subsequent rearrangement or substitution reactions.

Analyze the third synthesis route: The third image shows a simple HCl treatment, which might lead to the formation of a chloro group via a substitution reaction, but lacks the protection step for the alcohol.

Analyze the fourth synthesis route: The fourth image shows a tosyl chloride (TsCl) protection of the alcohol, followed by HCl treatment, and then deprotection with Bu4NF. This sequence is similar to the first but uses a different protecting group, which might affect the reaction conditions and outcomes.