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Test Bank for Organic Chemistry 2nd Edition by Klein Chapter Fourteen Topic: Introduction to Ethers Section: 14.1 1. Which of the following compounds is(are) classified as ethers? A) I B) II & IV C) III D) I & III E) all of these Ans: E Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 2. What is the common name for CH3CH2CH2OCH2CH2CH3? A) Dibutylether B) 1-propoxypropane C) 1-propoxyhexane D) dipropyl ether E) none of these Ans: D Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 3. What is the common name for (CH3)2CHCH2OCH(CH3)2? A) Diisobutylether B) isobutyl isopropyl ether C) sec-butyl isopropyl ether D) Diisopropylether E) none of these Ans: B

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Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 4. What is the IUPAC name for CH3CH2CH2CH2OCH2CH3? A) 1-ethoxybutane B) 1-butoxyethane C) ethyl butyl ether D) 1-ethoxyhexane E) none of these Ans: A Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Medium 5. What is the common name for the following compound? A) 1-butoxybutane B) sec-butyl isopropyl ether C) sec-butyl t-butyl ether D) n-butyl isopropyl ether E) none of these Ans: C Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 6. What is the IUPAC name for CH3CH2OCH2CH2CH2CH2OCH2CH3? A) 1,4-ethoxyoctane B) diethoxy butyl ether C) 1,2-diethoxymethane D) 1,2-diethoxyhexane E) 1,4-diethoxybutane Ans: E Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 7. What is the correct structure for benzyl phenyl ether?

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A) I B) II C) III D) IV E) none of these Ans: D Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 8. What is the correct structure for dibenzyl ether? A) I B) II C) III D) IV E) none of these Ans: B Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 9. What is the IUPAC name for the following compound? Ans: 3-isopropoxy-2-methyloctane Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 10. What is the IUPAC name for the following compound? Ans: 1-ethoxy-1-methoxy-3-propylcyclohexane Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 11. What is the IUPAC name for the following compound? Ans: E-4-isopropoxy-4,5-dimethylhex-2-ene

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Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 12. What is the IUPAC name for the following compound? Ans: (1S,3S)-1-ethoxy-3-methylcyclohexane Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 13. What is the IUPAC name for the following compound? Ans: 1,1,1-triethoxyethane Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 14. Provide the structure for 2-iodo-4-isopropyl-1-methoxybenzene. Ans: Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 15. Provide an IUPAC name for the following compound. Ans: 4-t-butyl-1-ethoxy-2-methylbenzene Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 16. Provide the structure for (2S,5R)-5-ethoxy-2-octanol. Ans: Topic: Nomenclature Section: 14.2 Difficulty Level: Hard 17. Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane. Ans:

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Topic: Nomenclature Section: 14.2 Difficulty Level: Easy 18. Draw all constitutional isomers with molecular formula C4H8O having an ether functional group and provide the IUPAC name for each isomer. Ans: Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 19. Draw all constitutional isomers with molecular formula C6H14O having an ether functional group and provide the IUPAC name for each isomer Ans: Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 20. Which one of the following compounds will have the highest boiling point? A) CH3CH2CH2CH2CH3 B) CH3CH2CH2CH2OH C) CH3CH2CH2OCH3 D) CH3CH2CH2Cl E) CH3CH2OCH2CH3 Ans: B Topic: Physical Properties Section: 14.3 Difficulty Level: Easy 21. Which one of the following compounds will have the highest boiling point? A) CH3CH2CH2CH2CH3 B) CH3CH2CH2CH2OH C) CH3CH2CH2OCH3 D) CH3CH2CH2Cl E) CH3CH2OCH2CHOH Ans: E Topic: Physical Properties Section: 14.3 Difficulty Level: Easy

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22. Which one of the following compounds will be least soluble in water? A) diethyl ether B) methyl propyl ether C) 1-butanol D) 2-butanol E) pentane Ans: E Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 23. Rank the following compounds in decreasing order of boiling points (highest to lowest) A) II>IV>I>III B) I>IV>II>III C) IV>I>II>III D) III>II>I>IV E) IV>II>I>III Ans: C Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 24. Rank the following compounds in decreasing order of water solubility (highest to lowest) A) II>IV>I>III B) I>IV>II>III C) IV>I>II>III D) III>II>I>IV E) IV>III>I>II Ans: E Topic: Physical Properties Section: 14.3 Difficulty Level: Medium 25. Which one of the following compounds has highest boiling point? Ans: III

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Topic: Crown ethers Section: 14.4 Difficulty Level: Medium 26. What is the IUPAC name for the following compound? A) 15-crown-5 B) 15-crown-4 C) 5-crown-15 D) 15-crown-15 E) none of these Ans: A Topic: Crown ethers Section: 14.4 Difficulty Level: Medium 27. What is the correct IUPAC name for the following compound? A) 12-crown-5 B) 12-crown-4 C) 4-crown-12 D) 12-crown-12 E) none of these Ans: B Topic: Crown ethers Section: 14.4 Difficulty Level: Easy 28. Which of the following crown ether solvates lithium ions? A) 12-crown-5 B) 12-crown-4 C) 15-crown-5 D) 18-crown-6 E) none of these Ans: B Topic: Crown ethers Section: 14.4 Difficulty Level: Easy 29. Which of the following crown ether solvates potassium ions? A) 12-crown-5

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B) 12-crown-4 C) 15-crown-5 D) 18-crown-6 E) none of these Ans: D Topic: Crown ethers Section: 14.4 Difficulty Level: Easy 30. Which of the following crown ether solvates sodium ions? A) 12-crown-5 B) 12-crown-4 C) 15-crown-5 D) 18-crown-6 E) none of these Ans: C Topic: Crown ethers Section: 14.4 Difficulty Level: Medium 31. Identify the missing reagent needed to carry out the following transformation. A) 12-crown-5 B) 12-crown-4 C) 15-crown-5 D) 18-crown-6 E) none of these Ans: C Topic: Crown ethers Section: 14.4 Difficulty Level: Medium 32. Identify the missing reagent needed to carry out the following transformation. A) 12-crown-5 B) 12-crown-4 C) 15-crown-5 D) 18-crown-6 E) none of these Ans: B

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Topic: Crown ethers Section: 14.4 Difficulty Level: Hard 33. Identify the missing reagent needed to carry out the following transformation. Ans: 18-crown-6 Topic: Crown ethers Section: 14.4 Difficulty Level: Hard 34. Identify the missing reagent needed to carry out the following transformation. Ans: 18-crown-6 Topic: Preparation of ethers Section: 14.5 Difficulty Level: Easy 35. Predict the product for the following reaction. A) Propene B) Diethyl ether C) 1-hexanol D) 1-propoxypropane Ans: D Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 36. Predict the product for the following reaction. Ans: Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 37. Provide a curved arrow mechanism for the formation of the product. Ans: Topic: Preparation of ethers

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Section: 14.5 Difficulty Level: Medium 38. Can you prepare diisopropyl ether as major product by heating 2-propanol in the presence of sulfuric acid? Explain your answer. Ans: No. Secondary and tertiary alcohols undergo elimination reactions when heated in the presence of a strong acid, such as sulfuric acid. The major product is an alkene and not an ether. 2-propanol is a secondary alcohol and it will yield propene as the major product. Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 39. Which one of the following reactions would produce t-butyl methyl ether in high yield? A) t-butyl chloride + sodium methoxide B) t-butanol + methanol in presence of H2SO4 at 140C C) t-butyl bromide + bromomethane in presence of NaOH D) sodium t-butoxide + bromomethane Ans: D Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 40. Which one of the following reactions would produce t-butyl methyl ether in high yield? A) CH3ONa + (CH3)3CBr B) CH3OH + (CH3)3COH in presence of H2SO4 at 140C C) CH3Cl + (CH3)3CBr in presence of NaOH D) (CH3)3CONa + CH3Br Ans: D Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 41. Which one of the following reactions would produce (S)-3-methoxyheptane in high yield?

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A) sodium (S)-3-heptoxide + bromomethane B) sodium (R)-3-heptoxide + bromomethane C) sodium methoxide + (S)-3-bromoheptane D) sodium methoxide + (R)-3-bromoheptane Ans: A Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 42. Predict the product for the following reaction. Ans: Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 43. Provide the reagents necessary to carry out the following conversion. Ans: 1. PBr3 2. Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard 44. Predict the product for the following reaction. Ans: Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium 45. Provide the reagents necessary to prepare the following compound using a Williamson ether synthesis. Ans: Topic: Preparation of ethers Section: 14.5 Difficulty Level: Medium

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46. Provide the reagents necessary to prepare the following compound using Williamson ether synthesis. Ans: Topic: Preparation of ethers Section: 14.5 Difficulty Level: Hard 47. Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product. Ans: Mechanism Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Medium 48. Predict the product for the following reaction. A) 3-methyl-3-pentanol B) 3-ethoxy-3-methylpentane C) 3-methyl-2-pentanol D) 2-ethoxy-3-methylpentane E) 1-ethoxy-3-methylpentane Ans: B Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 49. Predict the product for the following reaction. A) 1-ethyl-1-cyclohexanol B) 2-ethoxy-1-ethylcyclohexane C) 1-ethoxy-1-ethylcyclohexane D) 2-ethoxy-3-ethylcyclohexane E) 1-ethoxy-2-ethylcyclohexane Ans: C Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard

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50. Predict the product for the following reaction. A) 2-methyl-1-hexanol B) 2-methoxy-2-methylhexane C) 1-methoxy-2-methylhexane D) 2-methoxy-3-methylhexane E) 2-methyl-2-hexanol Ans: B Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 51. Predict the product for the following reaction. Ans: Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 52. . Predict the product for the following reaction. Ans: Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 53. . Provide the reagents necessary to prepare the following compound using alkoxymercuration-demercuration. Ans: OR OR Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 54. . Provide the reagents necessary to carry out the following conversion. Ans:

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Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy 55. Predict the product(s) for the following reaction. A) ethanol + 1-bromopropane B) 1-propanol + bromoethane C) 1-propanol + ethanol D) 1-bromopropane + bromoethane E) none of these Ans: D Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Easy 56. Predict the product(s) for the following reaction. A) ethanol + phenol B) phenol + iodoethane C) iodobenzene + ethanol D) iodobenzene + iodoethane E) none of these Ans: B Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 57. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) V Ans: C Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 58. Predict the product(s) for the following reaction.

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A) I B) II C) III D) IV E) V Ans: B Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 59. Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product. Ans: Mechanism Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard 60. Predict the product(s) for the following reaction. Ans: Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard 61. Predict the product(s) for the following reaction and provide a curved arrow mechanism for the formation of the product. Ans: Mechanism Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Hard 62. Predict the product(s) for the following reaction. Ans:

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Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 63. Predict the product(s) for the following reaction. Ans: Topic: Reactions of Ethers Section: 14.6 Difficulty Level: Medium 64. Explain why long-term storage of ethers can be dangerous. Ans: Ethers undergo autooxidation in the presence of atmospheric oxygen via a radical mechanism to form hydroperoxides. These hydroperoxides are unstable and can explode on heating. Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Easy 65. What is the IUPAC name for the following compound? A) 3-ethyl-2-methyloxirane B) 2-ethyl-3-methyloxirane C) 2-ethyl-1-methyloxypentane D) 1-ethyl-2-methyloxypentane E) none of these Ans: B Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 66. What is the IUPAC name for the following compound? A) 2-ethyl-3-isopropyl-2-methyloxirane B) 1-ethyl-2-isopropyl-1-methyloxirane C) 2,4-dimethyloxyhexane D) 1-ethyl-2,4-dimethyloxyhexane E) 3-ethyl-2-isopropyl-3-methyloxirane Ans: A

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Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 67. Provide the structure for tetrahydrofuran. Ans: Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 68. Provide the structure for oxetane. Ans: Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 69. Provide the IUPAC name for the following compound. Ans: (2S, 3S)-2-ethyl-3-isopropyloxirane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 70. Provide the IUPAC name for the following compound. Ans: (2S, 3R)-2-ethyl-3-phenyloxirane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 71. Provide the common name for the following compound. Ans: 1,4-dioxane Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 72. Provide the IUPAC name for the following compound. Ans: (1S,2R)-1-methyl-1,2-epoxycyclohexane

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Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 73. Provide the structure for (1S,2R)-1-ethyl-2-methyl-1,2-epoxycyclohexane. Ans: Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 74. Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane. Ans: Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 75. Predict the product for the following reaction. (E)-2-pentene + mCPBA A) I B) II C) III D) IV Ans: D Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 76. Predict the product for the following reaction. (Z)-3-hexene + mCPBA A) I B) II C) III D) IV Ans: A Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium

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77. Predict the product for the following reaction. A) I B) II C) III D) IV Ans: C Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 78. Predict the product for the following reaction. 1-methylcyclohexene + mCPBA Ans: Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 79. Provide the reagents necessary to carry out the following conversion. Ans: mCPBA Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 80. Predict the product for the following reaction. A) I B) II C) III D) IV Ans: D Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 81. Predict the product for the following reaction. Ans:

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Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 82. Provide the structure(s) of the product(s) in the following reaction sequence. Ans: Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 83. Predict the product for the following reaction. Ans: Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 84. Provide the reactants necessary to prepare the following compound. Ans: Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 85. Provide the reactants necessary to prepare the following compound. Ans: Topic: Preparation of epoxides Section: 14.8 Difficulty Level: Medium 86. Provide the reactants necessary to prepare the following compound. Ans: Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 87. Predict the product for the following reaction.

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Ans: Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 88. Predict the product for the following reaction. Ans: Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 89. Predict the product for the following reaction. Ans: Topic: Preparation of epoxides Section: 14.9 Difficulty Level: Medium 90. Predict the product for the following reaction. Ans: Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 91. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: C Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 92. Predict the product(s) for the following reaction.

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A) I B) II C) III D) IV E) none of these Ans: A Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 93. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: B Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 94. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: A Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 95. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: C

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Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 96. Provide the reagents necessary to carry out the following conversion. Ans: HCl Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 97. Provide the reagents necessary to carry out the following conversion. Ans: CH3OH/H2SO4 Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 98. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: A Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy 99. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: C Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy

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100. Predict the product(s) for the following reaction. A) I B) II C) III D) IV E) none of these Ans: D Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 101. Predict the product(s) for the following reaction. Ans: Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 102. Predict the product(s) for the following reaction. Ans: Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Medium 103. Provide the reagents necessary to carry out the following conversion. Ans: 1. mCPBA 2. CH3MgBr 3. H2O Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 104. Provide the reagents necessary to carry out the following conversion. Ans: 1. LiAlH4 2. H2O

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Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 105. Provide the reagents necessary to carry out the following conversion. Ans: 1. mCPBA 2. NH3 Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 106. Provide the reagents necessary to carry out the following conversion. Ans: 1. 2. H2O Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 107. Provide a stepwise curved arrow mechanism for the following reaction. Ans: Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Easy 108. What is the correct structure for 3-methyl-1-hexanethiol? Ans: Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 109. What is the correct structure for phenylthiol? Ans: Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium

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110. What is the IUPAC name for the following compound? Ans: 5-methyl-2-heptanethiol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Hard 111. What is the IUPAC name for the following compound? Ans: 5-mercapto-2-methyl-1-hexanol Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 112. What is the common name for the following compound? Ans: Methyl pentyl sulfide Topic: Nomenclature of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 113. What is the IUPAC name for the following compound? Ans: 2-ethylthiohexane Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Easy 114. Predict the product for the following reaction. Ans: Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 115. Predict the product for the following reaction. Ans:

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Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 116. Predict the product for the following reaction. Ans: Topic: Preparation of Thiols /sulfides Section: 14.11 Difficulty Level: Medium 117. Provide the reagents necessary to carry out the following conversion. Ans: Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Easy 118. Predict the major product for the following reaction. Ans: Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 119. Predict the major product for the following reaction. A) I B) II C) III D) IV E) none of these Ans: A Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 120. Predict the major product for the following reaction. Ans:

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Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 121. Predict the major product for the following reaction. A) I B) II C) III D) IV E) none of these Ans: D Topic: Reactions of Thiols/sulfides Section: 14.11 Difficulty Level: Medium 122. Predict the major product for the following reaction. A) I B) II C) III D) IV E) II & IV Ans: D Topic: Synthesis Section: 14.12 Difficulty Level: Medium 123. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Medium 124. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Hard

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125. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Hard 126. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Hard 127. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Hard 128. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Medium 129. Provide a stepwise synthesis for the following. Ans: Topic: Synthesis Section: 14.12 Difficulty Level: Medium 130. Provide a stepwise synthesis for the following. Ans:

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Topic: Spectroscopy Section: 14, 15.6, 16.10, 16.12 Difficulty Level: Medium 131. A compound with molecular formula C6H14O displays the following IR, 1HNMR and 13CNMR spectra. Propose a structure for this compound. IR: 1200cm-1 SDBS Ans: Topic: Spectroscopy Section: 14, 15.6, 16.10, 16.12 Difficulty Level: Medium 132. A compound with molecular formula C5H12O2 displays the following IR, 1HNMR and 13CNMR spectra. Propose a structure for this compound. IR: 1200cm-1