Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 4.. Ans: Topic: Preparation of Ethers Section: 14.5 Difficulty Level: Hard 37.. Topic: Preparation of ethers Section: 1
Trang 1Link full download:
Difficulty Level: Easy
2 What is the common name for CH3CH2CH2OCH2CH2CH3?
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
Trang 2Topic: Nomenclature of Ethers
Section: 14.2
Difficulty Level: Easy
4 What is the IUPAC name for CH3CH2CH2CH2OCH2CH3?
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
Difficulty Level: Medium
7 What is the correct structure for benzyl phenyl ether?
Trang 3Difficulty Level: Medium
8 What is the correct structure for dibenzyl ether?
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
Trang 4Topic: 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:
Trang 5Topic: 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
Difficulty Level: Easy
21 Which one of the following compounds will have the highest boiling point? A) CH3CH2CH2CH2CH3
Trang 622 Which one of the following compounds will be least soluble in water?
Difficulty Level: Medium
23 Rank the following compounds in decreasing order of boiling points (highest to lowest)
Difficulty Level: Medium
24 Rank the following compounds in decreasing order of water solubility (highest
Difficulty Level: Medium
25 Which one of the following compounds has highest boiling point?
Ans: III
Trang 7Topic: Crown ethers
Section: 14.4
Difficulty Level: Medium
26 What is the IUPAC name for the following compound?
Difficulty Level: Medium
27 What is the correct IUPAC name for the following compound? A) 12-crown-5
Difficulty Level: Easy
28 Which of the following crown ether solvates lithium ions? A) 12-crown-5
Difficulty Level: Easy
29 Which of the following crown ether solvates potassium ions? A) 12-crown-5
Trang 8Difficulty Level: Easy
30 Which of the following crown ether solvates sodium ions?
Difficulty Level: Medium
31 Identify the missing reagent needed to carry out the following transformation A) 12-crown-5
Difficulty Level: Medium
32 Identify the missing reagent needed to carry out the following transformation A) 12-crown-5
Trang 9Topic: 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
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
Trang 10Section: 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 140C
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?
Difficulty Level: Medium
41 Which one of the following reactions would produce (S)-3-methoxyheptane in high yield?
Trang 11A) 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
Trang 1246 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
Difficulty Level: Hard
49 Predict the product for the following reaction
Trang 1350 Predict the product for the following reaction
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
Difficulty Level: Hard
54 Provide the reagents necessary to carry out the following conversion Ans:
Trang 14Topic: Reactions of Ethers
Section: 14.6
Difficulty Level: Easy
55 Predict the product(s) for the following reaction A) ethanol + 1-bromopropane
Difficulty Level: Easy
56 Predict the product(s) for the following reaction A) ethanol + phenol
Difficulty Level: Medium
57 Predict the product(s) for the following reaction A) I
Difficulty Level: Medium
58 Predict the product(s) for the following reaction
Trang 15Difficulty 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:
Trang 16Topic: 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?
Difficulty Level: Medium
66 What is the IUPAC name for the following compound?
Trang 17Topic: 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
Trang 18Topic: 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
Difficulty Level: Medium
76 Predict the product for the following reaction
Trang 1977 Predict the product for the following reaction
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
Difficulty Level: Medium
81 Predict the product for the following reaction
Ans:
Trang 20Topic: 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
Trang 21Ans:
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
Difficulty Level: Easy
92 Predict the product(s) for the following reaction
Trang 22Difficulty Level: Easy
93 Predict the product(s) for the following reaction A) I
Difficulty Level: Medium
94 Predict the product(s) for the following reaction A) I
Difficulty Level: Medium
95 Predict the product(s) for the following reaction A) I
Trang 23Topic: 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
Difficulty Level: Easy
99 Predict the product(s) for the following reaction
Trang 24100 Predict the product(s) for the following reaction
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
Trang 25Topic: 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?