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Chapter Thirteen
1.
What is the IUPAC name for the following compound?
CH3CHCHCHCHCH3
OH
CH3
CH3
CH3
A)
4-isopropyl-3,4-dimethyl-2-butanol
B)
2,3,4-trimethyl-4-pentanol
C)
1,1,2,3-tetramethyl-4-pentanol
D)
3,4,5-trimethyl-2-hexanol
E)
3,4,5,5-tetramethyl-2-pentanol
2.
What is the IUPAC name for isobutyl alcohol?
A)
2-methyl-1-propanol
B)
2-methyl-1-butanol
C)
1-methyl-1-propanol
D)
1,1-dimethyl-1-ethanol
E)
3-methyl-1-propanol
3.
What is the IUPAC name for the following compound?
CH3CH2CCH2CH3
CH2CH3
OH
A)
1,1,1-triethylmethanol
B)
1,1-diethyl-1-propanol
C)
2-ethyl-3-pentanol
D)
3-ethyl-3-pentanol
E)
t-heptanol
4.
What is the IUPAC name for t-butyl alcohol?
A)
1-butanol
B)
2-methyl-1-propanol
C)
2-methyl-2-propanol
D)
2-butanol
E)
1,1-dimethyl-1-ethanol
5.
What is the IUPAC name for the following compound?
OH
A)
1-isopropyl-4-cyclopentanol
B)
3-isopropyl-1-cyclopentanol
C)
1-isopropyl-3-cyclopentanol
D)
1-isopropyl-4-hydroxycyclopentane
E)
None of these
6.
What is the correct structure for 1-chloro-3-ethyl-2-pentanol?
CH3CH2CCH2CH2Cl
CH2CH3
OH
CH3CHCHCH2CH2Cl
CH2CH3
OH
CH3CH2CHCHCH2Cl
CH2CH3
OH
CH3CH2CHCH2CHCl
CH2CH3
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
None of these
7.
What is the IUPAC name for the following compound?
Br
HO
A)
2-methyl-5-bromocyclohexanol
B)
3-bromo-2-methylcyclohexanol
C)
1-bromo-4-methylcyclohexanol
D)
4-bromo-6-methylcyclohexanol
E)
4-bromo-2-methylcyclohexanol
8.
What is the IUPAC name for the following compound?
CH3CH2C=CCH2CH3
CH3
CH2CH2OH
A)
3-methyl-4-ethyl-3-hexen-6-ol
B)
4-ethyl-3-methyl-3,6-hexenol
C)
3-ethyl-4-methyl-3-hexen-1-ol
D)
3-methyl-4-(2-hydroxyethyl)-3-hexene
E)
3-(2-hydroxyethyl)- 3-methyl-3-hexene
9.
What is the IUPAC name for the following compound?
OH
A)
4-penten-2-methyl-2-ol
B)
4-methyl-1-penten-2-ol
C)
2-methyl-4-penten-2-ol
D)
4-methyl-1-penten-4-ol
E)
4-hydroxy-4-methyl-1-pentene
10.
What is the IUPAC name for the following compound?
CH3
C
HO
HC
CCH2CH3
A)
(R)-3-hexyn-2-ol
B)
(S)-3-hexyn-2-ol
C)
(R)-2-hexyn-4-ol
D)
(S)-2-hexyn-4-ol
E)
(S)-2-hydroxy-3-hexyne
11.
What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?
OH
Br
Br
OH
Br Br
Br
Br
OH
CH3CH2CH2CH2CCH(CH3)OH
Br
Br
II
IV V
I
CH3CCH2CH2CH2CHOH
Br
Br
CH3
III
A)
I
B)
II
C)
III
D)
IV
E)
V
12.
What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?
V
IV
I
II
HO
HO
OH
OH
III
OH
A)
I
B)
II
C)
III
D)
IV
E)
V
13.
What is the IUPAC name for the following compound?
OH
14.
What is the IUPAC name for the following compound?
HO
15.
What is the IUPAC name for the following compound?
H Br
CH3
OH
16.
What is the IUPAC name for the following compound?
OH
17.
Provide the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?
18.
Provide the structure for 5-chloro-2-propyl-1-heptanol.
19.
Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.
20.
What is the IUPAC name for the following compound?
21.
What is the IUPAC name for the following compound?
22.
What is the IUPAC name for the following compound?
HO
23.
What is the IUPAC name for the following compound?
HO
24.
What is the IUPAC name for the following compound?
HOCH2CH2CH2OH
A)
1,2-butanediol
B)
isopropanol
C)
1-propanol
D)
1,3-propanediol
E)
1,2-ethanediol
25.
What is the IUPAC name for the following compound?
OH
OH
A)
cis-1,2-cyclopentanediol
B)
meso-1,2-cyclopentanediol
C)
(1R,2R)-1,2-cyclopentanediol
D)
(1R,2S)-1,2-cyclopentanediol
E)
(1S,2S)-1,2-cyclopentanediol
26.
What is the IUPAC name for the following compound?
OH OH
27.
Provide the structure for (2R, 3S) 2-bromo-1,3-pentanediol.
28.
Explain why cyclohexanol has a pKa of 18 and phenol has a pKa of 10. Use structural
drawings to explain your reasoning.
29.
Rank the following alcohols in decreasing order of acidity.
OH
Br
OH
F
OH
I
III III
30.
Which one of the following alcohols is most acidic?
O
OH
O
OH
OH
III III
31.
Rank the following alcohols in decreasing order of acidity. Explain your answer.
F
OH F
OH
OH
I
III
II
FF
32.
Rank the following alcohols in decreasing order of acidity.
O2N OH NC OH
OH
III III
33.
Predict the product(s) for the following reaction.
OH Na
34.
Predict the product for the following reaction.
OH 1. NaH
2. CH3CH2Br
35.
Provide the reagents necessary to carry out the following conversion.
CH3CH2CH2CHCH3
Br
CH3CH2CH2CH2CH2OH
36.
Predict the product(s) for the following reaction.
1. BH3
2. H2O2/NaOH/H2O
OH OH
OH
CH2OH
III III IV
+ enantiomer + enantiomer
A)
I
B)
II
C)
III
D)
IV
E)
None of these
37.
Predict the product for the following reaction.
1. Hg(OAc)2, H2O
2. NaBH4
OH
OH
OH CH2OH
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
None of these
38.
Provide the reagents necessary to carry out the following conversion.
(E)-3-methyl-3-hexene 3-methyl-3-hexanol
39.
Predict the major product for the following reaction.
H3O+
40.
Predict the product for the following reaction.
1. Hg(OAc)2, H2O
2. NaBD4
OH
OH D
OH D
OH
D OH
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
41.
Provide the reagents necessary to carry out the following conversion.
Br OH
42.
Provide the reagents necessary to carry out the following conversion.
OH
Cl
A)
NaOH/H2O
B)
1. NaOCH3, 2. H3O+
C)
1. (CH3)3COK, 2. BH3, 3. H2O2/NaOH/H2O
D)
1. (CH3)3COK, 2. H3O+
E)
B & D
43.
What is the oxidation state of the carbon atoms I and II in the following reaction?
I
O
O
H
II
A)
I. +1, II. +2
B)
I. +2, II. +2
C)
I. +1, II. +3
D)
I. +3, II. +2
E)
I. +2, II. +1
44.
What is the oxidation state of the carbon atoms I and II in the following reaction?
CH3CH
O
CH3COH
O
III
A)
I. +1, II. +2
B)
I. +2, II. +2
C)
I. +1, II. +3
D)
I. +3, II. +2
E)
I. +2, II. +1
45.
For the following conversion, identify if the starting material has been oxidized, reduced
or neither. Explain your answer.
OH O
46.
For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
Cl
Cl
47.
For the following conversion, identify if the starting material has been oxidized, reduced
or neither. Explain your answer.
OH O
48.
For the following conversion, identify if the starting material has been oxidized, reduced
or neither.
O
O
H
A)
reduced
B)
oxidized
C)
neither
D)
A & B
49.
Predict the product for the following reaction.
CH3CCH2CH2CH3
O
NaBH4/CH3OH
50.
Predict the product for the following reaction.
H
O
NaBH4/CH3OH
OH OH
OH
O
OH
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
51.
Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
O
H
O
H
OO
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
52.
Provide the reagents necessary to carry out the following conversion.
HC CCH2CH2CH3CH3CHCH2CH2CH3
OH
53.
Predict the product for the following reaction.
H
O
H2.Pd
OH OH
OH
O
OH
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
54.
Predict the product for the following reaction.
COCH3
O
O
NaBH4 / H2O
