CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W, Summaries of Chemistry

Download CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W and more Summaries Chemistry in PDF only on Docsity! 1 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W Short Answer Drawing Instructions: Draw structures corresponding to each of the given names. 1. Draw: 3-methyl-2-buten-1-ol 2. Draw: 2-phenyl-2-propanol 3. Draw: glycerol 4. Draw: 2, 4, 6-trinitrophenol IUPAC Naming Instructions: Provide proper IUPAC names. 5. Name: 6. Name: HOCH2CH2OH 7. Name: Exhibit 17-1 Rank the following groups of compounds from most acidic (1) to least acidic (4). Place the number corresponding to the compound's relative rank in the blank below the structure. 8. 9. 2 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W 10. 11. Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than tert-butoxide. Exhibit 17-2 Refer to the data below to answer the following question(s). pKas of Some Phenols Y pKa H 9.89 m-NO2 8.28 p-NO2 7.17 m-OCH3 9.65 p-OCH3 10.21 12. Refer to Exhibit 17-2. How do you account for the difference in acidity between meta and para-nitrophenol? Exhibit 17-3 To answer the following question(s), consider the reaction below: 13. Refer to Exhibit 17-3. The alcohol product is classified as a: a. 1 alcohol b. 2 alcohol c. 3 alcohol d. 4 alcohol 5 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W 25. 26. 27. 28. 29. 30. 31. Exhibit 17-9 Choose the best reagent(s) for carrying out the following conversions from the list provided below. Place the letter of the best choice in the blank to the left of the conversion. Reagents may be used more than once. a. 1. CH3MgBr, ether e. 1. p-TosCl, pyridine 2. H3O + 2. NaOH 6 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W b. 1. PBr3 f. CrO3, H2SO4, H2O 2. NaOH g. 1. NaBH4, ethanol c. 1. (CH3)3SiCl, (CH3CH2)3N 2. H3O + 2. CH3MgBr, ether h. Dess–Martin periodinane , CH2Cl2 3. H3O + d. 1. LiAlH4, ether 2. H3O + 32. _____ 33. _____ 34. _____ 35. _____ 36. Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source of carbon. 37. Outline the synthetic steps necessary to carry out the conversion below. You may use any organic or inorganic reagents you need. Show the structures of all intermediate compounds that would probably be isolated during the course of your synthesis, and show all necessary reagents. 7 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W 38. Synthesize the following alcohol starting with cyclohexene and bromocylopentane as the only organic starting materials. Show all reagents and all intermediates in your synthesis. Exhibit 17-10 Propose structures for alcohols that have the following 1 H NMR spectra. 39. C7H8O (neat solution; no solvent) Spectrum obtained from: SBDSWeb: http://www.aist.go.jp/RIODB/SDBS 10 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W PTS: 1 8. ANS: PTS: 1 9. ANS: PTS: 1 10. ANS: PTS: 1 11. ANS: Nonafluoro-2-methyl-2-propoxide anion is more stable than tert-butoxide anion because the electron-withdrawing fluoride atoms inductively delocalize the negative charge. Since nonafluoro-2-methyl-2-propoxide is more stable than tert-butoxide, it is a weaker base. PTS: 1 12. ANS: In m-nitrophenol, the inductive effect of the electron-withdrawing nitro group helps to stabilize the negative charge on oxygen. However, when the nitro group is para to the oxygen, direct conjugation of the negative charge on oxygen with the nitro group can occur. p-Nitrophenolate ion is, thus, more stable than m-nitrophenolate ion, and, as a result, forms more readily. PTS: 1 13. ANS: b 11 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W PTS: 1 14. ANS: PTS: 1 15. ANS: In E2 elimination, dehydration proceeds most readily when the two groups to be eliminated have a trans-diaxial relationship. In this compound, the only hydrogen with the proper geometric relationship to the OH group is at C6 so the major product of this reaction is 3-methylcyclohexene. PTS: 1 16. ANS: PTS: 1 17. ANS: (R)-2-heptanol PTS: 1 18. ANS: 12 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W PTS: 1 19. ANS: d PTS: 1 20. ANS: A PTS: 1 21. ANS: c PTS: 1 22. ANS: PTS: 1 23. ANS: 15 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W PTS: 1 37. ANS: PTS: 1 38. ANS: 16 CHEM 2425. Chapter 17. Alcohols and Phenols (homework) W PTS: 1 39. ANS: benzyl alcohol PTS: 1 40. ANS: 1-ethylcyclohexanol PTS: 1