Organic Chemistry, 8e (Wade) Chapter 14 Ethers, Epoxides, and Thioethers 1) What is the hybridization of the oxygen atom in dialkyl ethers? A) sp 3 B) sp 2 C) sp D) s E) p Answer: A Diff: 1 Section: 14.2 2) Which of the following corresponds to the COC bond angle in dimethyl ether? A) 60° B) 94° C) 110° D) 122° E) 180° Answer: C Diff: 1 Section: 14.2 3) Which has the higher boiling point, diethyl ether or butan-1-ol? Briefly explain. Answer: Butan-1-ol has the higher boiling point since intermolecular hydrogen bonding can occur. Molecules of diethyl ether are incapable of hydrogen bonding with each other. Diff: 1 Section: 14.2 4) Which of the following is not a property of ethers which makes them good solvents in organic reactions? A) They dissolve a wide range of polar substances. B) They have relatively high boiling points for their molecular weights. C) They are nonhydroxylic. D) They dissolve a wide range of nonpolar substances. 1 Copyright © 2013 Pearson Education, Inc.
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Organic Chemistry, 8e (Wade)Chapter 14 Ethers, Epoxides, and Thioethers
1) What is the hybridization of the oxygen atom in dialkyl ethers?A) sp3
B) sp2C) spD) sE) pAnswer: ADiff: 1Section: 14.2
2) Which of the following corresponds to the COC bond angle in dimethyl ether?A) 60°B) 94°C) 110°D) 122°E) 180°Answer: CDiff: 1Section: 14.2
3) Which has the higher boiling point, diethyl ether or butan-1-ol? Briefly explain.Answer: Butan-1-ol has the higher boiling point since intermolecular hydrogen bonding can occur. Molecules of diethyl ether are incapable of hydrogen bonding with each other.Diff: 1Section: 14.2
4) Which of the following is not a property of ethers which makes them good solvents in organic reactions?A) They dissolve a wide range of polar substances.B) They have relatively high boiling points for their molecular weights.C) They are nonhydroxylic.D) They dissolve a wide range of nonpolar substances.E) They are normally unreactive toward strong bases.Answer: BDiff: 2Section: 14.2
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5) Draw structures which show the hydrogen bonding interaction that exists between water and dimethyl ether.Answer:
Diff: 2Section: 14.2
6) Give two properties of ethers which allow them to be commonly used as solvents in organic reactions.Answer: (any two of the following)1. Dissolve a wide variety of both polar and nonpolar compounds.2. Tend to be unreactive under a large number of reaction conditions.3. Have low boiling points; easily removed from product mixture.Diff: 2Section: 14.2
7) What complex results when BF3 is dissolved in dimethyl ether?Answer: (CH3)2O∙BF3Diff: 2Section: 14.2
8) Anisole is known by two other names. Give either of them.Answer: methoxybenzene or methyl phenyl etherDiff: 1Section: 14.3
9) Provide the structure of 3-methoxyfuran.Answer:
Diff: 1Section: 14.3
10) Provide a structural representation of 2-ethoxypentane.Answer:
Diff: 1Section: 14.3
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11) Provide a structural representation of isopropyl tert-butyl ether.Answer: (CH3)2CHOC(CH3)3Diff: 1Section: 14.3
12) Provide a structural representation of 1,2-epoxybutane (also called 2-ethyloxirane).Answer:
Diff: 1Section: 14.3
13) What is the correct IUPAC name for the following compound?
A) 3-methyl-3,4-epoxypentan-1-olB)
B) 5-hydroxy-3-methyl-2,3-epoxypentaneC) 1-(2-hydroxyethyl)-1,2-dimethyloxiraneD) 3,4-epoxy-3-methylpentan-1-olAnswer: ADiff: 2Section: 14.3
14) Which of the following is not a true statement?A) Dioxanes are six-membered ring ethers.B) Furans are five-membered ring ethers.C) Oxiranes are three-membered ring ethers.D) Oxetanes are five-membered ring ethers.E) Pyrans are six-membered-ring ethers.Answer: DDiff: 2Section: 14.3
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15) What is the complete systematic IUPAC name for the following compound?
A) 4-(1-methylethoxy)-4-isopropyl-4-methylpent-2-eneB) 4-isopropyl-2,4-dimethylhept-5-en-3-olC) isopropyl-(4-isopropyl-4-methylbut-2-enyl) etherD) (E)-4-isopropoxy-4,5-dimethylhex-2-eneE) 4-isopropyl-4-methylbut-2-en-isopropyl etherAnswer: DDiff: 2Section: 14.3
16) Provide the structure of 4,4-dimethylpyran.Answer:
Diff: 2Section: 14.3
17) Provide the IUPAC name of the compound shown below.
Answer: 1,1-diethoxycyclohexaneDiff: 2Section: 14.3
18) Provide a structural representation of oxetane.Answer:
Diff: 2Section: 14.3
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19) Provide a structural representation of 3-ethylfuran.Answer:
Diff: 2Section: 14.3
20) Provide a structural representation of cis-3-ethyl-1,2-epoxycyclopentane.Answer:
Diff: 2Section: 14.3
21) Provide an acceptable name for the compound shown below.
CH3OCH2CH(CH3)2Answer: isobutyl methyl ether or 1-methoxy-2-methylpropaneDiff: 2Section: 14.4
22) Provide an acceptable name for the compound shown below.
Answer: trans-2-ethoxycyclohexan-1-olDiff: 2Section: 14.4
23) Provide an acceptable name for the compound shown below.
Answer: propylene oxide or methyloxiraneDiff: 2Section: 14.4
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24) Provide the structure of the fragment in the mass spectrum of dipropyl ether that results from a cleavage.
Answer:
Diff: 2Section: 14.4
25) In mass spectrometry, what is the most common fragmentation of ethers?Answer: Cleavage next to one of the carbon atoms bonded to oxygen.Diff: 2Section: 14.4
26) Propose a structure for the ether of formula C4H10O with the following 1H NMR signals: δ 1.20 (triplet, 6H), δ 3.45 (quartet, 4H) (ppm).Answer: CH3CH2OCH2CH3Diff: 2Section: 14.4
27) Propose a structure for the ether of formula C4H10O with the following 1H NMR signals: δ 0.95 (triplet, 3H), 1.52 (multiplet, 2H), 3.30 (singlet, 3H), 3.40 (triplet, 2H) (ppm).Answer: CH3CH2CH2OCH3Diff: 2Section: 14.4
28) Propose a structure for the ether of formula C4H10O with the following 1H NMR signals: δ 1.13 (doublet, 6H), 3.30 (singlet, 3H), 3.65 (septet, 1H) (ppm).Answer: (CH3)2CHOCH3Diff: 2Section: 14.4
29) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.4
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30) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.4
31) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.4
32) Provide an acceptable name for the compound shown below.
Answer: 1,4-dioxaneDiff: 3Section: 14.4
33) What is the chemical shift of the carbon bound to oxygen in ethers in 13C NMR?Answer: δ 65 to δ 90Diff: 3Section: 14.4
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34) Provide the major organic product of the following.
Answer:
Diff: 3Section: 14.4
35) The Williamson ether synthesis occurs by the ________ mechanistic pathway.Answer: SN2Diff: 1Section: 14.5
36) Show the best method for preparing methoxycyclopentane via the Williamson ether synthesis.Answer:
Diff: 1Section: 14.5
37) Provide the major organic product in the reaction below.
CH3CH2CH2OH
Answer: CH3CH2CH2OCH2PhDiff: 1Section: 14.5
38) Provide the major organic product in the reaction below.
Answer:
Diff: 1Section: 14.5
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39) Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane?A) sodium (S)-2-butoxide + iodoethaneB) sodium (R)-2-butoxide + iodoethaneC) sodium ethoxide + (S)-2-iodobutaneD) sodium ethoxide + (R)-2-iodobutaneE) Both B and C would work equally well.Answer: BDiff: 2Section: 14.5
40) Which of the following is an acceptable way to synthesize t-butyl ethyl ether?A) treatment of t-butyl bromide with sodium ethoxideB) treatment of ethyl bromide with sodium t-butoxideC) heating a mixture of ethanol and t-butanol in sulfuric acidD) treating t-butyl bromide with Hg(OAc)2E) treating t-butanolwith Hg(OAc)2Answer: CDiff: 2Section: 14.5
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41) Which of the following reactions is classified as a Williamson ether synthesis?A)
B)
C)
D)
E)
Answer: BDiff: 2Section: 14.5
42) Show the best method for preparing 4-propoxytoluene via the Williamson ether synthesis.Answer:
Diff: 2Section: 14.5
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43) Provide the sequence of reactions by which propoxycyclohexane can be prepared through a Williamson ether synthesis.Answer:
Diff: 2Section: 14.5
44) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.5
45) Provide the major organic product of the reaction shown below.
Answer:
Diff: 2Section: 14.5
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46) Provide the major organic product of the reaction shown below.
Answer:
Diff: 2Section: 14.5
47) Show the best Williamson ether synthesis for the following target molecule.
Answer:
Diff: 2Section: 14.5
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48) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.5
49) Provide the necessary reagents to complete the following reaction.
Answer:
Diff: 3Section: 14.5
50) Show the reagents necessary to prepare 1-ethoxy-1-methylcyclopentane from 1-methylcyclopentene.Answer: 1. Hg(OAc)2, CH3CH2OH2. NaBH4Diff: 1Section: 14.6
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51) When cyclohexene is subjected to mercuration in methanol and the resulting mixture is reduced with sodium borohydride, the major organic product is:A) a meso ether.B) a 1:1 mixture of enantiomeric ethers.C) a meso diol.D) a 1:1 mixture of enantiomeric diols.E) methoxycyclohexane.Answer: EDiff: 2Section: 14.6
52) When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results?A) 3-ethoxypentaneB) 1-methoxypentaneC) 1-ethoxypentaneD) 2-ethoxypentaneE) 2-methoxypentaneAnswer: EDiff: 2Section: 14.6
53) Which of the following reactions or series of reactions will lead to the formation of methoxycyclohexane?A)
B)
C)
D)
E)
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Answer: DDiff: 2Section: 14.6
54) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.6
55) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.6
56) Show how propyl cyclopentyl ether can be prepared starting with cyclopentene and using an alkoxymercuration-demercuration route.Answer:
Diff: 2Section: 14.6
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57) Provide the major organic product in the reaction below.
CH3CH2CHCH2 →
Answer: CH3CH2CHCH3 ∣OCH2CH3
Diff: 2Section: 14.6
58) Show the reagents necessary for the conversion of 1-bromo-1-methylcyclopentane to1-ethoxy-1-methylcyclopentane.Answer: CH3CH2OH, heatDiff: 2Section: 14.6
59) Complete the following reaction by drawing a structure for the expected product.
Answer:
Diff: 2Section: 14.6
60) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.6
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61) Provide two reasons why it would be difficult to prepare ethoxycyclopentane via an intermolecular dehydration route from ethanol and cyclopentanol.Answer: 1. Secondary alcohols tend to yield alkenes under these conditions.2. Symmetrical ethers would be produced as well.Diff: 2Section: 14.7
62) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.7
63) Can one prepare di-sec-butyl ether in good yield by heating butan-2-ol in the presence of sulfuric acid? Explain.Answer: This would not be an appropriate method of preparing di-sec-butyl ether in good yield. When butan-2-ol, a 2° alcohol, is heated in the presence of strong acid, the major product is 2-butene, the elimination product.Diff: 2Section: 14.7
64) When hexan-1-ol is treated with conc. H2SO4 at moderate temperatures, ________ is formed via a(n) ________ mechanism.A) di-n-hexyl ether, SN2B) di-n-hexyl ether, SN1C) di-n-hexyl ether, E2D) di-n-propyl ether, E1E) hex-1-ene, SN1Answer: ADiff: 2Section: 14.7
65) Some ethers can be prepared by heating the appropriate alcohol in the presence of sulfuric acid. Can di-sec-butyl ether be prepared from sec-butanol by this route? Explain your answer.Answer: No. sec-Butanol is a secondary alcohol. Secondary and tertiary alcohols predominantly undergo elimination when heated in acid.Diff: 2Section: 14.7
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66) Suggest a reasonable mechanism for the reaction shown below.
Answer:
or
Diff: 2Section: 14.7
67) What are the expected products of the reaction of PhOCH3 with concentrated HI?A) phenol and methanolB) phenol and iodomethaneC) iodobenzene and methanolD) iodobenzene and iodomethaneAnswer: BDiff: 1Section: 14.8
68) Provide the major organic product(s) in the reaction below.
Answer:
Diff: 1Section: 14.8
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69) Di-n-pentyl ether can be converted to 1-bromopentane by treatment with HBr through essentially a(n) ________ mechanism.A) SN2B) SN1C) E2D) E1E) ring openingAnswer: ADiff: 1Section: 14.8
70) Treatment of tetrahydrofuran with excess HBr results in the formation of what major organic product?A) 1-bromobutaneB) 1,2-dibromobutaneC) 1,4-dibromobutaneD) 1-bromopentaneE) 1,5-dibromopentaneAnswer: CDiff: 2Section: 14.8
71) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.8
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72) Provide the major organic product of the reaction shown below.
Answer:
Diff: 2Section: 14.8
73) Provide the major organic product of the reaction shown below.
Answer: Br(CH2)6BrDiff: 2Section: 14.8
74) Predict the products of the following reaction and give a reasonable mechanism for their formation.
Answer:
Diff: 2Section: 14.8
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75) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.8
76) What is the major organic product which results when tetrahydrofuran is reacted with excess HBr?A) 1,2-dibromobutaneB) 1,3-dibromobutaneC) 1,4-dibromobutaneD) 4-bromobutan-1-olE) 3-bromobutan-1-olAnswer: CDiff: 3Section: 14.8
77) Provide the major organic product in the reaction below.
Answer:
Diff: 3Section: 14.8
78) The presence of what product of the autooxidation of ethers makes the distillation of ethers dangerous?Answer: dialkyl peroxidesDiff: 2Section: 14.9
79) When ethers are stored in the presence of oxygen, what explosive materials can result from autoxidation of the ether?Answer: hydroperoxides or dialkylperoxidesDiff: 2Section: 14.9
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80) Which of the following compounds would undergo autoxidation most readily?A) dibenzyl etherB) MTBEC) diethyl etherD) isobutyl phenyl etherAnswer: ADiff: 2Section: 14.9
81) What term is given to the sulfur analogues of ethers?Answer: sulfides or thioethersDiff: 1Section: 14.10
82) Provide a common name for the following compound.
Answer: allyl ethyl sulfideDiff: 1Section: 14.10
83) What is the correct IUPAC name of the structure below?
A) 2-ethylthio-5-methoxymethylcyclopent-1,3-dieneB) 1-ethylthio-3-methoxymethylcyclopent-1,4-dieneC) 1-mercaptoethyl-4-methoxymethylcyclopent-1,2-dieneD) 5-methoxymethyl-3-thioethylcyclopenta-1,3-dieneAnswer: ADiff: 2Section: 14.10
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84) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.10
85) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.10
86) Which of the following is produced by the reaction of (CH3CH2)2S with CH3CH2I?A) CH3CH2CH2CH2I
B) (CH3CH2)3S+ I-
C) (CH3CH2)3SD) CH3SCH2CH2CH3E) CH3CH2SCH2CH2IAnswer: BDiff: 2Section: 14.10
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87) In biological systems, sulfonium salts such as SAM serve what function?A) esterifying agentsB) epoxidizing agentsC) alkylating agentsD) nucleophilic agentsE) crown ether agentsAnswer: CDiff: 2Section: 14.10
88) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.10
89) Provide the major organic product of the reaction shown below.
Answer:
Diff: 2Section: 14.10
90) Provide the structure of the sulfonium salt that results when (CH3CH2)2S reacts with CH3CH2Cl. Through what mechanistic path is this reaction occurring?Answer: (CH3CH2)3S+ Cl-; SN2Diff: 2Section: 14.10
91) Why are sulfonium salts good alkylating agents?Answer: Sulfonium salts are good alkylating agents because the leaving group is an uncharged sulfide.Diff: 2Section: 14.10
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92) Provide the major organic product in the reaction below.
Answer:
Diff: 1Section: 14.11
93) Provide the major organic product in the reaction below.
Answer:
Diff: 1Section: 14.11
94) Show the reagents necessary to prepare trans-1,2-cyclopentanediol from cyclopentene.Answer: 1. PhCO3H
2. H3O+
Diff: 1Section: 14.11
95) When trans-hex-3-ene is treated with PhCO3H, the major organic product is:A) a meso epoxide.B) a 1:1 mixture of enantiomeric epoxides.C) a meso diol.D) a 1:1 mixture of enantiomeric diols.E) hexan-3-ol.Answer: BDiff: 2Section: 14.11
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96) Magnesium monoperoxyphthalate is often used as a reagent in what process?A) reductive aminationB) dehydrationC) halohydrin formationD) epoxidationE) Williamson ether synthesisAnswer: DDiff: 2Section: 14.11
97) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.11
98) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.11
99) Show the reagents necessary to prepare 1,2-epoxy-1-methylcyclopentane from cyclopentanone.Answer: 1. CH3MgBr2. conc. H2SO43. PhCO3HDiff: 2Section: 14.11
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100) Identify all of the following reagents that could be used to accomplish the following transformation.(More than one answer is possible.)
A) mCPBAB) DMDC) cold KMnO4D) 1) Br2 / H2O, 2) NaHAnswer: A, B, DDiff: 2Section: 14.11
101) Provide the major organic product of the following.
Answer:
Diff: 2Section: 14.11
102) Through what mechanism can a 1,2-halohydrin be converted into an epoxide?A) SN1B) SN2C) E2D) electrophilic additionE) polymerizationAnswer: BDiff: 2Section: 14.11
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103) Suggest a reasonable mechanism for the reaction shown below.
Answer:
Diff: 2Section: 14.11
104) Provide the major organic product in the reaction below.
HOCH2(CH2)2CH2Br Answer:
Diff: 3Section: 14.11
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105) Which of the following reactions or series of reactions will lead to formation of trans-2-methoxycyclohexanol?A)
B)
C)
D)
E)
Answer: DDiff: 2Section: 14.12
106) What is the stereochemistry of the product of the acid hydrolysis of trans-2,3-epoxybutane?Answer: mesoDiff: 2Section: 14.12
107) What results when but-1-ene is subjected to the following reaction sequence: (1) Cl2, H2O, (2) NaOH, (3) H3O+?A) a meso epoxideB) a 1:1 mixture of enantiomeric epoxidesC) a meso diolD) a 1:1 mixture of enantiomeric diolsE) butan-2-olAnswer: DDiff: 3Section: 14.12
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108) Use arrows to show correct electron flow in the mechanism for the reaction below. Include all intermediate structures correctly drawn with formal charges.
Answer:
Diff: 3Section: 14.12
109) What results when cyclopentene oxide is treated with aqueous base?A) a racemic mixture of trans-1,2-diolsB) a meso trans-1,2-diolC) a racemic mixture of cis-1,2-diolsD) a meso cis-1,2-diolE) cyclopenteneAnswer: ADiff: 2Section: 14.13
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110) Draw the correct structure of the expected product of the following reaction.
Answer:
Diff: 2Section: 14.13
111) What reagents are necessary for the following transformation?
Answer:
Diff: 3Section: 14.13
112) Provide a structure for the expected product of the following reaction.
Answer:
Diff: 3Section: 14.13
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113) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.14
114) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.14
115) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.14
116) Show the reagents necessary to prepare trans-2-deuteriocyclohexan-1-ol from cyclohexene.Answer: 1. PhCO3H2. LiAlD4Diff: 3Section: 14.14
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117) Show the reagents necessary to prepare the compound below from cyclohexanone.
Answer: 1. CH3MgBr2. conc. H2SO43. PhCO3H
4. CH3CH2O-
Diff: 3Section: 14.14
118) Provide the major organic product in the reaction below.
Answer:
Diff: 3Section: 14.14
119) Provide the major organic product in the reaction below.
Answer:
Diff: 3Section: 14.14
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120) What is the major difference in the structure of the product formed in a Grignard reaction when an alkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde or ketone followed by work-up with H3O+?A) The alkyl group from the Grignard reagent will be bonded to the α-carbon of the alcohol product.B) The alkyl group from the Grignard reagent will be bonded to the β-carbon of the alcohol product.C) The alkyl group from the Grignard reagent will form an ether product rather than an alcohol product.D) Two equivalents of the Grignard will result in the bonding of two alkyl groups to the α-carbon of the alcohol product.E) The epoxide will protonate the Grignard reagent resulting an alkane product.Answer: BDiff: 1Section: 14.15
121) Show the reagents necessary to prepare 2-phenylethanol from bromobenzene.Answer: 1. Mg, ether2. oxirane3. H3O+
Diff: 2Section: 14.15
122) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.15
123) What compound is formed when ethylene oxide is reacted with n-pentyllithium followed by treatment with aqueous acid?A) 1-heptanolB) 2-heptanolC) heptanalD) 2-heptanoneE) pentanalAnswer: ADiff: 2Section: 14.15
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124) What compound is formed when methyloxirane is reacted with ethylmagnesium bromide followed by treatment with aqueous acid?A) 1-pentanolB) 2-pentanolC) 2-methyl-1-butanolD) 2-methyl-2-butanolE) 3-methyl-1-butanolAnswer: BDiff: 2Section: 14.15
125) What compound is formed when 2,2-dimethyloxirane is treated with ethanol containing a trace of HCl?A) 2-ethoxy-2-methyl-1-propanolB) 1-ethoxy-2-methyl-2-propanolC) 2-ethoxy-2-methyl-2-propanolD) 2-ethoxy-1-butanolE) 1-ethoxy-2-butanolAnswer: ADiff: 2Section: 14.15
126) Provide the major organic product of the following reactions.
Answer:
Diff: 2Section: 14.15
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127) Provide the major organic product in the reaction below.
Answer:
Diff: 2Section: 14.15
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