Chapter Twenty Three
1.
What is the structure for 1-butanamine?
A)
CH3CH2CH2CH2NH2
B)
CH3CH2NHCH2CH(CH3)2
C)
(CH3CH2)2NCH2CH(CH3)2
D)
(CH3CH2)4N+ OH–
E)
(CH3CH2)3CNH2
Ans:
A
2.
What is the common name for the following compound?
N
A)
ethylethylisobutyl amine
B)
diethylisobutyl amine
C)
sec-butyldiethylamine
D)
2-diethylaminobutane
E)
None of these
Ans:
C
3.
What is the IUPAC name for the following compound?
H
N
A)
N-ethylhexanamine
B)
N-ethylcyclohexanamine
C)
N-cyclohexylethanamine
D)
N-ethylcyclopentanamine
E)
N-ethylaniline
4.
What is the IUPAC name for the following compound?
N
A)
N-cyclopentyl-N-methylcylohexanamine
B)
N-cyclohexyl-N-methylcylohexanamine
C)
N-cyclopentyl-N-methylcylopentanamine
D)
cyclohexylcyclopentylmethylamine
E)
N-pentyl-N-methylhexanamine
Ans:
A
5.
What is the IUPAC name for the following compound?
H
N
A)
1-methyl-N-propyl-1-butananmine
B)
4-methyl-5-octanamine
C)
1-ethyl-N-propyl-1-pentanamine
D)
N-butyl-2-pentanamine
E)
N-methylpropyl-1-butanamine
Ans:
D
6.
What is the IUPAC name for the following compound?
NH2
7.
What is the IUPAC name for the following compound?
NH2
Ans:
(1S,2S)-2-methyl-1-cyclopentanamine
8.
What is the structure for 3-chloro-N-ethylpentanamine?
9.
What is the structure for N-ethylbenzylamine?
10.
What is the structure for N,N-diethylaniline?
11.
What is the IUPAC name for the following compound?
OH NH2
Ans:
7-amino-5-isopropyl-3-octanol
12.
What is the IUPAC name for the following compound?
HO
O
NH2
Ans:
4-amino-2,2-diethylhexanoic acid
13.
What is the IUPAC name for the following compound?
O NH2
HO
14.
What is the IUPAC name for the following compound?
O
NH2
Ans:
3-amino-4-ethylcyclohexanone
15.
What is the IUPAC name for the following compound?
NH2
Ans:
(1R,6R)-6-methylcyclohex-2-enamine
16.
Arrange the following compounds in decreasing (highest to lowest) order of boiling
point and explain your choice.
CH3CH2CH2CH2NH2CH3CH2N(CH3)2CH3CH2CH2NHCH3
III III
A)
II>III>I
B)
I>III>II
C)
II>III>I
D)
III>II>I
E)
I>II>III
17.
Arrange the following compounds in decreasing (highest to lowest) order of boiling
point.
A)
III>I>IV>II
B)
I>III>IV>II
C)
I>IV>III>II
D)
I>III>II>IV
E)
III>I>II>IV
Ans:
B
18.
Which one of the following compounds is the strongest base?
NH2
O2N
NH2NH2
NH2
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
III & IV
Ans:
D
19.
Rank the following compounds in decreasing (strongest to weakest) order of basicity.
NH2
O2N
NH2NH2
NH2
III III IV
A)
I>III>II>IV
B)
II>III>I>IV
C)
IV>II>III>IV
D)
IV>III>II>I
E)
III>II>I>IV
20.
Arrange the following compounds in decreasing (strongest to weakest) order of basicity.
III III IV
CH3CH2NH2(CH3CH2)2NH
NH3
(CH3CH2)3N
A)
I>III>II>IV
B)
II>III>I>IV
C)
IV>II>I>III
D)
IV>III>II>I
E)
II>I>IV>III
Ans:
C
21.
Arrange the following compounds in decreasing (strongest to weakest) order of basicity.
III III IV
p-toluidine p-methoxyanilinep-nitroaniline
aniline
A)
I>III>II>IV
B)
II>III>I>IV
C)
IV>III>II>I
D)
IV>I>II>III
E)
II>I>IV>III
Ans:
D
Ans:
D
22.
Arrange the following compounds in decreasing (strongest to weakest) order of basicity.
NH2
CF3
NH2
OCH3
O NH2
NH2
III III IV
A)
I>III>II>IV
B)
II>III>I>IV
C)
IV>III>II>I
D)
IV>I>II>III
E)
II>IV>I>III
23.
Arrange the following compounds in decreasing (weakest to strongest) order of basicity.
N
NH2
III III IV
NH2
NO2
H
N
A)
IV<II<I<III
B)
III<II<IV<I
C)
II<I<III<IV
D)
II<III<I<IV
E)
None of
Ans:
C
Ans:
E
24.
Which one of the following is a stronger base? Explain why.
NH
N
H
III
25.
Pyridoxamine, aka vitamin B6 has the following structure. Which nitrogen is more
basic? Explain your choice.
NH3C
HO
CH2NH2
CH2OH
1
2
26.
Nicotine present in tobacco has the following structure. Which nitrogen is more basic
and explain your choice.
N
N
CH3
1
2
27.
Chloroquine is used as an antimalarial drug. Rank the three nitrogen atoms in decreasing
(strongest to weakest) order of basicity.
NCl
HN
N
I
II
III
A)
III>I>II
B)
I>III>II
C)
I>IV>III>II
D)
I>III>II>IV
E)
III>II>I
28.
Predict the product for the following reaction.
CN H2/Ni
III III
NH2
NH2CN
IV
NH2
O
V
NH
A)
I
B)
II
C)
III
D)
IV
E)
V
29.
Predict the product for the following reaction.
Br 1. NaCN
2. LiAlH4
3. H2O
NH2
NH2
CN
III III
NH2
O
IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
C
Ans:
B
30.
Provide the reagent(s) necessary to carry out the following conversion.
NO2NH2
A)
H2/Ni
B)
1. LiAlH4 2. H2O–
C)
Fe/HCl
D)
NaBH4/CH3OH
E)
all of these
31.
Predict the product for the following reaction.
1. LiAlH4
2. H2O
NH2
O
III III
NH2NH2
NH2
OH
H2N
OH
H2N
O
IV
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans
A
Ans:
C
32.
Predict the product for the following reaction.
NH
O
1. LiAlH4
2. H2O
NH NH
OH
NH2
O
III III
H2N
OH
H2N
O
IV
V
A)
I
B)
II
C)
III
D)
IV
E)
V
33.
Provide the reagents necessary to carry out the following conversion for the following
reaction.
N
O
N
Ans
1. LiAlH4
2. H2O
34.
Predict the product for the following reaction sequence.
O
OH SOCl2CH3NH2
pyridine
1. LiAlH4
2. H2O
35.
Provide the reagents necessary to convert (S)-3-methyl-3-phenylpentanoic acid to
(S)-3-methyl-3-phenylpentanamine.
36.
Provide the reagents necessary to carry out the following conversion.
CH2Br CH2CH2NH2
Ans:
37.
Provide the reagents necessary to carry out the following conversion.
CH2CN CH2CH2NH2
38.
Predict the product for the following reaction.
1. NaN3
2. LiAlH4
3. H2O
Br
NHNH2NH2
NNH2
III III
N
NH
IV
A)
I
B)
II
C)
III
D)
IV
E)
III & IV
Ans:
B
39.
Predict the product for the following reaction.
Br
1. NaN3
2. LiAlH4
40.
Predict the product for the following reaction and provide a stepwise curved arrow
mechanism for the formation of the product.
1. LiAlH4
2. H2O
N3
41.
Predict the product for the following reaction sequence.
NaN3 1. LiAlH4
2. H2O
mCPBA
OH
NH2
N3
OH
NH2
OH
OH
NH2
OH
N3
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
42.
Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?
A)
1-bromopentane
B)
1-bromo-3-methylbutane
C)
2-bromo-3-methylpentane
D)
1-bromo-2,3-dimethylbutane
E)
2-bromo-2,3-dimethylbutane
Ans:
E
43.
Predict the product(s) for the following reaction.
NH
O
O
1. KOH
2. CH3CH2CH2CH2Br
3. H3O+
COH
COH
O
O
NH2
CNH2
COH
O
O
NH2
NH2
CNH2
COH
O
O
N
O
O
III
III IV
++
+
A)
I
B)
II
C)
III
D)
IV
E)
None of these
Ans:
A
44.
Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.
45.
Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.
46.
Predict the product for the following reaction.
NH
O
O
KOH Br H3O+
47.
Predict the product(s) for the following reaction.
O
NH2
H2SO4, NaBH3CN
NCH2CH3NHCH2CH3HO NHCH2CH3
H3CH2CHN NHCH2CH3
N
H
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
48.
Predict the product(s) for the following reaction.
H2SO4, NaBH3CN
O
NH2
N
HO NH
N
O HN
III
III IV
A)
I
B)
II
C)
III
D)
IV
E)
None of these
49.
Provide the reagents necessary to carry out the following conversion.
H
N
2. CH3CH2NH2, H2SO4, NaBH3CN
Ans:
D