TB chapter 11-with answers PDF

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CHAPTER 11—ETHERS, EPOXIDES, AND SULFIDES MULTIPLE CHOICE 1. Which of the following are ethers?

a. b. c. d.

only 1 and 2 only 1 and 4 only 1, 2 and 3 1, 2, 3 and 4

ANS: D 2. Which of the following are epoxides?

a. b. c. d.

only 2 and 3 only 3 and 4 only 2, 3 and 4 1, 2, 3 and 4

ANS: B 3. What is the correct assignment of the names of the following ethers?

a. b. c. d.

1 = oxirane; 2 = oxetane; 3= oxolane 1 = oxetane; 2 = oxirane; 3= oxane 1 = oxane; 2 = oxetane; 3= dioxane 1 = oxirane; 2 = oxolane; 3= oxetane

ANS: A

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4. What is the correct assignment of the names of the following ethers?

a. b. c. d.

1 = oxirane; 2 = oxetane; 3 = oxane 1 = oxirane; 2 = oxitane; 3 = oxane 1 = oxane; 2 = dioxane; 3 = oxetane 1 = oxirane; 2 = oxolane; 3 = oxane

ANS: D 5. Which of the following are thiols?

a. b. c. d.

only 1 only 1 and 4 only 2 and 3 1, 2, 3 and 4

ANS: A 6. Which of the following statements are true? 1. 2. 3. a. b. c. d.

ethanol is more soluble in water than dimethyl ether ethanol has a higher boiling point than dimethyl ether ethanol has the same molecular weight as dimethyl ether only 1 only 1 and 2 only 1 and 3 1, 2 and 3

ANS: D

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7. What is the IUPAC name of the following compound?

a. b. c. d.

cis-1,4-anisole cis-4-methoxyanisole cis-1,4-dimethoxycyclohexane para-dianisole

ANS: C 8. What is the IUPAC name of the following compound?

a. b. c. d.

ethyl isopropyl thiol 2-ethylsulfanylpropane ethyl isopropyl disulfide isopropylsufanylethane

ANS: B 9. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: B

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10. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: C 11. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: A 12. Which of the following reactions provides anisole (PhOCH3) in a high yield? a. phenol + sodium methoxide b. bromobenzene + bromomethane c. sodium phenoxide (PhONa) + bromomethane d. bromobenzene + sodium methoxide ANS: C

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13. Which of the following reactions provides tert-butyl methyl ether in a high yield? a. potassium tert-butoxide + iodomethane b. sodium methoxide + tert-butyl bromide c. methanol + tert-butyl alcohol in the presence of KOH d. iodomethane + tert-butyl bromide in the presence of KOH ANS: A 14. Which of the following ethers cannot be prepared by a Williamson ether synthesis? a. tert-butyl phenyl ether b. isopropyl methyl ether c. anisole d. tert-butyl methyl ether ANS: A 15. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: B 16. What is the major organic product obtained from the following reaction?

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 a. b. c. d.

1 2 3 4

ANS: D 17. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: B 18. What type of reactive intermediate is formed in the reaction of tert-butyl methyl ether with HBr to give tert-butyl bromide? a. tert-butyl anion b. tert-butoxide c. tert-butyl radical d. tert-butyl cation ANS: D 19. What type of mechanism accounts for the cleavage of dibutyl ether upon treatment with HBr to give two moles of 1-bromobutane? a. SN1 b. SN2 c. E1 d. E2 ANS: B 20. What type of mechanism accounts for the cleavage of tert-butyl methyl ether upon treatment with HBr? a. SN1 b. SN2 c. E1 d. E2

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ANS: A 21. What are the major products obtained upon treatment of anisole, PhOCH3, with excess HBr? a. phenol and methanol b. bromobenzene and bromomethane c. phenol and bromomethane d. bromobenzene and methanol ANS: C 22. What are the major products obtained upon treatment of tert-butyl methyl ether with excess HBr? a. tert-butyl alcohol and methanol b. tert-butyl bromide and methanol c. tert-butyl alcohol and bromomethane d. tert-butyl bromide and bromomethane ANS: D 23. What type of reactive intermediate is formed in the reaction of methyl propene with methanol in the presence of an acid catalyst to give methyl tert-butyl ether (MTBE)? a. tert-butyl cation b. tert-butyl radical c. tert-butyl anion d. tert-butoxide ANS: A 24. What is the major organic product obtained from the following reaction?

a. b. c. d.

only 1 only 2 only 3 both 2 and 3

ANS: C 25. What is the major organic product obtained from the following reaction?

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 a. b. c. d.

1 2 3 4

ANS: A 26. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: A 27. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: A

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28. What is the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

H 2O H2SO4, H2O LiAlH4 followed by H3O+ KMnO4

ANS: C 29. What is the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

peroxyacid Br2, H2O; followed by NaOH, H2O OsO4; followed by NaHSO3 H2O, H2SO4

ANS: A 30. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: D

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31. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: C 32. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: A

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33. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: B 34. What is the major organic product obtained from the following reaction?

a. b. c. d.

only 1 only 2 only 3 both 2 and 3

ANS: B 35. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: B

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36. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: C 37. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: D 38. What is the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

CH3MgBr; followed by H3O+ H2O, NaOH LiAlH4 followed by H3O+ KMnO4

ANS: C

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39. What is the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

O3 peroxyacid OsO4; followed by NaHSO3 H2O, H2SO4

ANS: B 40. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: A 41. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: C

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42. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: C 43. What is the major organic product obtained from the following sequence of reactions?

a. b. c. d.

1 2 3 4

ANS: A 44. Which of the following general structures can be made by sequential reaction of epichlorohydrin with appropriate nucleophiles?

a. b. c. d.

1 2 3 4

ANS: C

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45. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: C 46. What is the name of the following compound?

a. b. c. d.

6-crown-12 12-crown-6 18-crown-12 18-crown-6

ANS: B 47. Which of the following ions forms the strongest complex with 18-crown-6? a. Li+ b. Na+ c. K+ d. Rb+ ANS: C 48. Which of the following statements is not true? a. Crown ethers complex alkali metal ions by donation of lone pairs from the oxygen atoms to the metal cation. b. Metal ion complexes of crown ethers dissolve in nonpolar aprotic organic solvents c. Addition of 18-crown-6 to a solution of benzyl bromide and potassium cyanide in a nonpolar solvent increases the rate of nucleophilic substitution. d. 18-Crown-6 is a planar molecule

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ANS: D 49. Which of the following synthetic routes is used in industry to provide epichlorohydrin?

a. b. c. d.

1 2 3 4

ANS: D 50. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: C

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51. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: B 52. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: B 53. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: A

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54. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

ANS: C 55. What would be the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

H 3O + H2O, NaOH LiAlH4 followed by H3O+ H 2O 2

ANS: D 56. What would be the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

H 2O 2 NaIO4 H2O, NaOH H2SO4

ANS: B

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57. What would be the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

CH3OH, H2SO4 NaOEt, followed by CH3OH NaOEt, followed by CH3I CH3OCH3

ANS: C 58. What would be the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

CH3S−Na+ CH3SH, H2SO4 CH3OH, Na2S CH3I, H2SO4

ANS: A PROBLEM 1. What is the IUPAC name of the following compound?

ANS: 2-ethoxyethanol 2. What is the IUPAC name of the following compound?

ANS: 1,2-diethoxyethane 3. What is the IUPAC name of the following compound?

ANS: 1-methoxycyclohex-1-ene

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4. What is the IUPAC name of the following compound?

ANS: dicyclopentyl ether (oxadicyclopentane) 5. Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis.

ANS:

6. Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis.

ANS:

7. What is the major organic product obtained from the following reaction?

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ANS:

8. What is the major organic product obtained from the following reaction?

ANS:

9. What is the major organic product obtained from the following reaction?

ANS:

10. What is the major organic product obtained from the following reaction?

ANS:

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11. What is the major organic product obtained from the following reaction?

ANS:

12. What is the major organic product obtained from the following reaction?

ANS:

13. What is the major organic product obtained from the following reaction?

ANS:

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