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_Q04_QT.jpg" alt="The figure illustrates the structure of a molecule. A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 2 is single bonded to C H 3 below and C H 3 on the lower left, each in the form of a line. C 5 is wedge bonded to O above. C 5 is single bonded on the lower right to C 2 of a 3-carbon triangular ring in a vertical orientation with C 1 occupying the bottommost vertex. O is single bonded on the upper right to C 5 of a benzene ring in a vertical orientation with C 1 occupying the topmost vertex. The benzene ring contains alternating double bonds between C 1 and C 2, C 3 and C 4, and c 5 and C 6." />

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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

12. Alcohols, Ethers, Epoxides and Thiols

Williamson Ether Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Williamson Ether Synthesis

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Multiple Choice

Which of the following will successfully synthesize the given target?

The figure illustrates a reaction. The 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 5 is single bonded to C H 2 in the form of a line. C H 2 is single bonded to B r on the upper left. The second reactant has the following structure: A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 2 is single bonded to C H 3 below and C H 3 on the lower left, each in the form of a line. C 5 is wedge bonded to O H above. C 5 is single bonded on the lower right to C 2 of a 3-carbon triangular ring in a vertical orientation with C 1 occupying the bottommost vertex. The third reactant is N a H written over the reaction arrow. T H F is written under the reaction arrow.

The figure illustrates a reaction. The reaction contains four 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 5 is single bonded to O H. The second reactant has the following structure: A 5-carbon alkane chain is depicted as a line structure using 4 zigzag lines. C 2 is single bonded to C H 3 below and C H 3 on the lower left, each in the form of a line. C 5 is dash bonded to B r above. C 5 is single bonded on the lower right to C 2 of a 3-carbon triangular ring in a vertical orientation with C 1 occupying the bottommost vertex. The third reactant is N a O H written over the reaction arrow. The fourth reactant is H 2 O written under the reaction arrow.

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Identify the target molecule: The target molecule is an ether with a phenyl group attached to an oxygen atom, which is connected to a chiral carbon bearing a cyclopropyl group and a tert-butyl group.

Analyze the first reaction: The first reaction involves a phenyl bromide and an alcohol in the presence of NaH and THF. NaH is a strong base that can deprotonate the alcohol to form an alkoxide ion, which can then perform a nucleophilic substitution on the phenyl bromide to form an ether.

Analyze the second reaction: The second reaction is similar to the first, with a slight difference in the structure of the alcohol. The same mechanism applies, where NaH deprotonates the alcohol to form an alkoxide, which then attacks the phenyl bromide.

Analyze the third reaction: The third reaction involves phenol and an alkyl bromide in the presence of NaOH and water. NaOH can deprotonate phenol to form a phenoxide ion, which can then perform a nucleophilic substitution on the alkyl bromide to form an ether.

Analyze the fourth reaction: The fourth reaction is similar to the third, with a different stereochemistry of the alkyl bromide. The mechanism remains the same, where NaOH deprotonates phenol to form a phenoxide ion, which attacks the alkyl bromide.