Which of the following 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_Q03_QT.jpg" alt="The figure illustrates the structure of a molecule. A 4-carbon alkane chain is depicted as a line structure using 3 zigzag lines. C 1 is single bonded to O C H 3 on the upper left. C 2 is single bonded to C H 3 on the upper right and C H 3 on the upper left, each in the form of a line. C 3 is wedge bonded to O H below." />

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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

Alcohol Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

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Multiple Choice

Which of the following is the best synthesis of the given molecule?

The figure illustrates a reaction. The reaction contains three reactants. The first reactant has the following structure: A 4-carbon alkene chain is depicted as a line structure using 3 zigzag lines. A double bond is present between C 3 and C 4. C 1 is single bonded to O C H 3 on the upper left. C 2 is single bonded to C H 3 on the upper left and C H 3 on the upper right, each in the form of a line. The second reactant is B H 3 written over the reaction arrow. The third reactants are N a O H and H 2 O 2 written under the reaction arrow.

The figure illustrates a reaction in which the product has to be determined. The reaction contains three reactants. The first reactant has the following structure: A 4-carbon alkene chain is depicted as a line structure using 3 zigzag lines. A double bond is present between C 3 and C 4. C 1 is single bonded to O C H 3 on the upper left. C 2 is single bonded to C H 3 on the upper left and C H 3 on the upper right, each in the form of a line. The second reactant is H B r written over the reaction arrow. The third reactant is H 2 O 2 written under the reaction arrow.

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Identify the target molecule: The target molecule is a secondary alcohol with a methoxy group and a tertiary butyl group.

Analyze the first reaction: Hydroboration-oxidation (BH3, NaOH, H2O2) adds water across a double bond in an anti-Markovnikov fashion, resulting in an alcohol at the less substituted carbon.

Analyze the second reaction: Oxymercuration-demercuration (Hg(OAc)2, NaBH4) adds water across a double bond in a Markovnikov fashion, resulting in an alcohol at the more substituted carbon.

Analyze the third reaction: Acid-catalyzed hydration (H2O, H2SO4) also adds water in a Markovnikov fashion, similar to oxymercuration-demercuration.

Analyze the fourth reaction: Radical addition of HBr (HBr, H2O2) adds HBr across a double bond in an anti-Markovnikov fashion, resulting in a bromide at the less substituted carbon, not an alcohol.