Chapter Fourteen
1.
What is the common name for CH3CH2CH2OCH2CH2CH3?
A)
dibutylether
B)
1-propoxypropane
C)
1-propoxyhexane
D)
dipropyl ether
E)
none of these
Ans:
D
2.
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
3.
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
4.
What is the common name for the following compound?
O
A)
1-butoxybutane
B)
sec-butyl isopropyl ether
C)
sec-butyl t-butyl ether
D)
n-butyl isopropyl ether
E)
none of these
5.
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
6.
What is the correct structure for benzyl phenyl ether?
O CH2OCH2
H3C O CH3CH2O
III
III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
D
Ans:
C
7.
What is the correct structure for dibenzyl ether?
O CH2OCH2
H3C O CH3CHOCH
CH3CH3
III
III IV
CH3CH2OCOCH2CH3
CH3
OCH2CH3
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
B
8.
What is the IUPAC name for the following compound?
O
O
O
OO
A)
15-crown-5
B)
15-crown-4
C)
5-crown-15
D)
15-crown-15
E)
none of these
Ans:
A
9.
What is the correct IUPAC name for the following compound?
O O
OO
A)
12-crown-5
B)
12-crown-4
C)
4-crown-12
D)
12-crown-12
E)
none of these
10.
What is the IUPAC name for the following compound?
O
Ans:
3-isopropoxy-2-methyloctane
11.
What is the IUPAC name for the following compound?
OO
Ans:
1-ethoxy-1-methoxy-3-propylcyclohexane
Ans:
B
12.
What is the IUPAC name for the following compound?
O
13.
What is the IUPAC name for the following compound?
CH3CH2OCOCH2CH3
CH3
OCH2CH3
Ans:
1,1,1-triethoxyethane
14.
Provide the structure for (2S,5R)-5-ethoxy-2-octanol.
15.
Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane.
Ans:
E-4-isopropoxy-4,5-dimethylhex-2-ene
16.
Which one of the following compounds will have the highest boiling point?
A)
CH3CH2CH2CH2CH3
B)
CH3CH2CH2CH2OH
C)
CH3CH2CH2OCH3
D)
CH3CH2CH2Cl
E)
CH3CH2OCH2CH3
17.
Which one of the following compounds will have the highest boiling point?
A)
CH3CH2CH2CH2CH3
B)
CH3CH2CH2CH2OH
C)
CH3CH2CH2OCH3
D)
CH3CH2CH2Cl
E)
CH3CH2OCH2CHOH
Ans:
E
18.
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
Ans:
B
19.
Rank the following compounds in decreasing order of boiling points (highest to lowest)
CH3CH2CH2CH2OH CH3CH2OCH2CH3CH3OCH3HOCH2CH2CH2OH
III III IV
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
20.
Rank the following compounds in decreasing order of water solubility (highest to
lowest)
CH3CH2CH2CH2OH CH3CH2OCH2CH2CH3CH3CH2OH
CH3CH2OCH2CH2OH
III IV
III
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
21.
Which one of the following compounds will have highest boiling point?
HO
OO O
HO
OH
III III
HO IV
Ans:
Ans:
C
22.
Predict the product for the following reaction.
2 CH3CH2CH2OH
H2SO4
1400C
A)
propene
B)
Diethyl ether
C)
1-hexanol
D)
1-propoxypropane
23.
Predict the product for the following reaction.
2-cyclopentylethanol H2SO4
1400C
24.
Provide a curved arrow mechanism for the formation of the product.
HO
O
OH
H2SO4
O
O
Ans:
D
25.
Can you prepare diisopropyl ether as major product by heating 2-propanol in the
presence of sulfuric acid? Explain your answer.
major product.
26.
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
27.
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 140C
C)
CH3Cl + (CH3)3CBr in presence of NaOH
D)
(CH3)3CONa + CH3Br
Ans:
D
28.
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
29.
Predict the product for the following reaction.
OH
1. NaH
2. CH3CH2CH2I
30.
Provide the reagents necessary to carry out the following conversion.
OH O
Ans:
A
31.
Predict the product for the following reaction.
Br
OH NaOH
heat
32.
Provide the reagents necessary to prepare the following compound using a Williamson
ether synthesis.
O
33.
Provide the reagents necessary to prepare the following compound using Williamson
synthesis.
(CH3)2CHCH2OCH(CH3)2
34.
Predict the product for the following reaction and provide a curved arrow mechanism
for the formation of the product.
Br OH
NaOH
35.
Predict the product for the following reaction.
1. Hg(OAc)2, CH3CH2OH
2. NaBH4
3-methyl-2-pentene
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
36.
Predict the product for the following reaction.
1. Hg(OAc)2, CH3CH2OH
2. NaBH4
1-ethyl-1-cyclohexene
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
37.
Predict the product for the following reaction.
1. Hg(OAc)2, CH3OH
2. NaBH4
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
38.
Predict the product for the following reaction.
1. Hg(OAc)2,
2. NaBH4
OH
Ans:
C
39.
.
Predict the product for the following reaction.
1. Hg(OAc)2, CH3CH2OH
2. NaBH4
40.
.
Provide the reagents necessary to prepare the following compound using
alkoxymercuration-demercuration.
O
41.
.
Provide the reagents necessary to carry out the following conversion.
OC(CH3)3
42.
Predict the product(s) for the following reaction.
O
HBr
excess
A)
ethanol + 1-bromopropane
B)
1-propanol + 1-bromoethane
C)
1-propanol + ethanol
D)
1-bromopropane + 1-bromoethane
E)
none of these
43.
Predict the product(s) for the following reaction.
HI
excess
O
A)
ethanol + phenol
B)
phenol + 1-iodoethane
C)
iodobenzene + ethanol
D)
iodobenzene + 1-iodoethane
E)
none of these
Ans:
B
Ans:
D
44.
Predict the product(s) for the following reaction.
HBr
excess
O
Br CH2OH
I
OH CH2OH
II
OH CH2Br
III
+++
OCH2Br OH
IV
Br CH2Br
V
++
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
C
45.
Predict the product(s) for the following reaction.
HI
excess
O
OI I I OH
I II III
OH I
IV
O I
V
+
A)
I
B)
II
C)
III
D)
IV
E)
V
46.
Predict the product(s) for the following reaction and provide a curved arrow mechanism
for the formation of the product.
HBr
excess
O
Ans:
B
47.
Predict the product(s) for the following reaction.
HI
excess
O
O
48.
Predict the product(s) for the following reaction and provide a curved arrow mechanism
for the formation of the product.
O
HBr
excess
49.
Predict the product(s) for the following reaction.
HI
1 mol
O
50.
Predict the product(s) for the following reaction.
O
HBr
excess
51.
Explain why long-term storage of ethers can be dangerous.
mechanism to form hydroperoxides. These hydroperoxides are unstable and can
explode on heating.
52.
What is the IUPAC name for the following compound?
O
A)
2-ethyl-1-methyloxirane
B)
1-ethyl-2-methyloxirane
C)
2-ethyl-1-methyloxypentane
D)
1-ethyl-2-methyloxypentane
E)
none of these
53.
What is the IUPAC name for the following compound?
O
A)
2-ethyl-1-isopropyl-2-methyloxirane
B)
1-ethyl-2-isopropyl-1-methyloxirane
C)
2,4-dimethyloxyhexane
D)
1-ethyl-2,4-dimethyloxyhexane
E)
none of these
Ans:
B
54.
Provide the structure for tetrahydrofuran.
Ans:
B