Link full download test bank for organic chemistry 2nd edition by klein

Test Bank for Organic Chemistry 2nd Edition by Klein Chapter Fourteen Topic: Introduction to Ethers Section: 14.1 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 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 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 Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 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 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 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 What is the correct structure for benzyl phenyl ether? A) I B) II C) III D) IV E) none of these Ans: D Topic: Nomenclature Section: 14.2 Difficulty Level: Medium 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 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 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: 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 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 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 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 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 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? 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 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: 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 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 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 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: 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 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 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 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 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: mCPBA CH3MgBr H2O Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 104 Provide the reagents necessary to carry out the following conversion Ans: LiAlH4 H2O Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 105 Provide the reagents necessary to carry out the following conversion Ans: mCPBA NH3 Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Hard 106 Provide the reagents necessary to carry out the following conversion Ans: 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 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: 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: 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 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: 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