Chapter 10 Amines
Multiple Choice
1. Which is the correct structure for diphenylamine? (Sec. 10.3)
NH2
H
a)
N
b)
CH2
c)
NH2
d)
NH2
2. Which is the IUPAC name for the following structure? (Sec. 10.3)
CH3 H
H3C C
N CH3
CH3
a)
b)
c)
d)
N-methyl-tert-butylamine
N-methyl-1,1-dimethylethylamine
N-methyl-2-methyl-2-propanamine
tert-butyl methyl amine
3. Which is the structure for N,N-dimethyl-3-hexanamine? (Sec. 10.3)
CH3
NHCH3
a) CH3NCH2CH2CH2CH3
b) CH3CH2CH2CCH2CH3
NHCH3
CH3
CH3
c) CH3CH2CCH2CH2CH2NH2
N CH3
d) CH3CH2CHCH2CH2CH3
CH3
116
Chapter 10 Amines
4. Which pairs of names and structures match correctly? (Sec. 10.3)
I. piperidine
A.
II. pyrrolidine
B.
III. pyrrole
C.
IV. pyridine
D.
V. cyclohexylamine
NH
NH
NH2
NH
E.
N
a)
b)
c)
d)
I and D, II and B
III and A, IV and E
V and C, III and B
III and D, IV and E
5. Which structures are secondary amines? (Sec. 10.2)
CH3
NCH3
CH3CHCH2NH2
H
I
II
NH
NH2
III
a)
b)
c)
d)
IV
I, II
II, III
III, IV
II, IV
117
Chapter 10 Amines
6. Which is the classification of the following amine? (Sec. 10.2)
CH3
H3CCH2CH2CH2
a)
b)
c)
d)
N CH3 Cl
1°
2°
3°
4°
7. Which is the name for the following compound? (Sec. 10.3)
NH3 Cl
a)
b)
c)
d)
phenylammonium chloride
phenyltrihydrogenammonium chloride
aniline chloride
benzylammonium chloride
8. Which is the name for the following compound? (Sec. 10.3)
O
H2N
a)
b)
c)
d)
COH
4-carboxy aniline
1-amino-4-carboxybenzene
benzylamine carboxylic acid
4-aminobenzoic acid
9. Which compound is the strongest base? (Sec. 10.5)
CH3
a) CH3NH2
b) CH3NH
CH3
c) CH3NCH3
118
d) CH3NH3 OH
Chapter 10 Amines
10. Which compound is the strongest base? (Sec. 10.5)
NH2
a)
NH2
NH2
b)
c)
Br
NH2
d)
NO2
CH3
11. Which reactions will proceed predominately to products as written? (Sec. 10.6)
I. CH3NH2
+
H2O
CH3NH3 + OH
O
O
II. CH3NH2 +
CH3NH3 + CH3CO
CH3COH
CH3
III. CH3NH2 +
CH3
CH3NCH3
CH3NH + CH3NCH3
H
IV. CH3NH2 +
a)
b)
c)
d)
CH3NH3 +
NH3
NH2
I, II
III, IV
II, IV
I, III
12. When the following compounds are dissolved in water at the same concentrations, which one will have
the lowest pH (i.e., most acidic)? (Sec. 10.5)
CH3
CH3
a)
CH2NCH3
CH2NCH3 OH
b)
CH3
CH3
CH3
c)
CH2NCH3 Cl d)
CH2NCH3 Cl
CH3
H
119
Chapter 10 Amines
13. Arrange the amines in order of increasing basicity (weakest first). (Sec. 10.5)
NH2
NH2
NH2
H
N
CH3
I
a)
b)
c)
d)
II
IV
III
IV, II, III, I
II, I, III, IV
I, II, III, IV
II, I, IV, III
14. At pH 5.0, the ratio of morpholine and morpholinium ion is 1:1622. Which is the pKb of morpholine?
(Sec. 10.5)
a)
b)
c)
d)
3.21
5.79
8.21
9.25
15. Guanidine has a pKb value of 0.4. Which is the ratio of guanidine to its conjugate acid at blood pH of
7.4? (Sec. 10.5)
a)
b)
c)
d)
10-6.2:1
10+6.2:1
1:1
2.5:1
16. Which are the correct positions for the site of protonation of the bases, guanidine and imidazole?
(Sec. 10.6)
NH
I
H2N
C
N
III
NH2
N
II
a)
b)
c)
d)
IV
H
I, III
II, IV
I, IV
II, III
120
Chapter 10 Amines
17. Arrange the amines in order of increasing boiling point (lowest first). (Sec. 10.4)
CH2CH3
CH2CH3
N
CH3CH2
CH2CH3
CH3CH2NH2
I
a)
b)
c)
d)
CH3CH2NH
II
CH3CH2NH3 Cl
III
IV
II, III, I, IV
III, I, IV, II
IV, II, III, I
IV, III, I, II
18. Arrange the amines in order of increasing boiling point (lowest first). (Sec. 10.4)
methylamine
I
a)
b)
c)
d)
ethylamine
II
propylamine
III
cyclohexylamine
IV
IV, III, II, I
I, II, III, IV
III, II, I, IV
II, I, IV, III
19. Arrange the amines in order of increasing solubility in water (least first). (Sec. 10.4)
CH2CH3
CH3CH2
N
CH2CH3
CH2CH3
I
a)
b)
c)
d)
CH3CH2NH2
II
CH3CH2NH
CH3CH2NH3 Cl
III
II, III, I, IV
IV, II, III, I
IV, III, II, I
I, III, II, IV
20. Arrange the amines in order of increasing solubility in water (least first). (Sec. 10.4)
ethylamine
I
a)
b)
c)
d)
methylamine
II
propylamine
III
II, I, III, IV
IV, II, III, I
IV, III, I, II
I, III, II, IV
121
cyclohexylamine
IV
IV
Chapter 10 Amines
21. Arrange the following in order of increasing strength of the hydrogen bonds (weakest first).
(Sec. 10.4)
I. H2NH
III. H2O
a)
b)
c)
d)
OH2
II. H3N
HNH2
HOH
IV. H3N
HOH
I, II, III, IV
II, I, IV, III
II, IV, I, III
I, IV, II, III
22. Which is the product of the following reaction? (Sec. 10.7)
NO2
Fe, HCl
H3C
CH3
ethanol/water
NO2
NH3Cl
a)
b)
HOOC
COOH
H3C
CH3
NO2
Cl
c)
Cl
d)
H3C
CH3
H3C
122
CH3
Chapter 10 Amines
23. Which is the product of the following reaction? (Sec. 10.8)
NH2
NaNO2
HCl, 0° C
CH3
N
+
N Cl-
NH2
NO2
O 2N
a)
NH2
b)
c)
d)
O2N
CH3
CH3
CH3
CH3
24. Which is the product of the following reaction? (Sec. 10.8)
NH2
H3PO2
NaNO2
HCl, 0° C
CH3
NH3Cl
a)
NH2
NH2
c)
b)
O2P
CH3
d)
PO2
CH3
CH3
123
NO2
Chapter 10 Amines
25. The following mixture was extracted with 1 M HCl, followed by 1 M NaOH, followed by ether.
Which compound is recovered from the acid solution? (Sec. 10.6)
H3C
a)
b)
c)
d)
CH3
N
OH
I
II
H3C
CH
CH3
III
I
II
III
None of the above
Fill in the Blank
1. The name of the following compound is _______________________________. (Sec. 10.3)
CH3
N
H
CH3
2. The name of the following compound is ______________________________. (Sec. 10.3)
Br
N
H
3. The name of the following compound is _________________________________. (Sec. 10.3)
N
+
N Cl-
CH3
124
Chapter 10 Amines
4. The starting material needed to complete the following reaction is,
NH2
Fe, HCl
Br
Br
(Sec. 10.7
5. The starting material needed to complete the following reaction is,
H3PO2
CH3
H3C
CH3
6. The reactants needed to complete the following reaction are,
NH2
OH
(Sec. 10.8)
7. The major product of the following reaction is,
NH2
1) NaNO2, HCl, H2O, 0° C
O
2) warm solution
OH
(Sec. 10.8)
125
(Sec. 10.8)
Chapter 10 Amines
8. The order of decreasing basicity of the following amines is (1 is the most basic),
CH3
O2N
NH2
N
H3C
N
CH3
H3C NH2
(Sec. 10.5)
9. The order of increasing basicity of the following compounds is (1 is the least basic),
CH3
OH
O
NH2
OH
(Sec. 10.5)
10. The order of increasing boiling point of the following compounds is (1 is lowest boiling),
CH3
OH
O
NH2
OH
(Sec. 10.5)
126
Chapter 10 Amines
True-False
1. The name of the following compound is N-cyclopentylethanamine. (Sec. 10.3)
H
N
CH2CH3
2. The name of the following compound is 3,5-dimethylpiperidine. (Sec. 10.3)
H
N
H3C
CH3
3. The strongest base in the following group is aniline. (Sec. 10.5)
NH2
NH2
N
4. The strongest base in the following group is methylthiocyclohexane. (Sec. 10.5)
HN
CH3
O
CH3
S
CH3
5. Cyclohexanamine is a 2º amine. (Sec. 10.2)
6. tert-butyl methyl amine is a 3º amine. (Sec. 10.2)
7. The pKa for ethyl ammonium ion is 10.8 (ethyl amine pK b is 3.2). (Sec. 10.5)
8. Tertiary amines are generally stronger bases than secondary amines. (Sec. 10.5)
9. The equilibrium for the reaction of p-nitroaniline and acetic acid lies to the right. (Sec. 10.6)
10. The reaction of aniline with nitrous acid after warming yields phenol. (Sec. 10.8)
127
Chapter 10 Amines
Answers
Multiple Choice
1. b
2. c
3. d
4. d
5. d
6. d
7. a
8. d
9. b
10. d
11. c
12. c
13. c
14. b
15. a
16. c
17. a
18. b
19. d
20. c
21. b
22. b
23. c
24. c
25. a
Fill in the Blank
1. N-methyl 2-methylcyclohexanamine
2. 3-bromopiperidine
3. 3-methylbenzene diazonium chloride
4.
NO2
Br
Br
128
Chapter 10 Amines
5.
N
+
N Cl-
6.
1) NaNO2, H2O, HCl, O°
2) warm
7.
OH
HO
O
8. 4, 3, 2, 1
9. 1, 3, 4, 2
10. 1, 3, 2, 4
True-False
1. F
2. T
3. F
4. F
5. F
6. F
7. T
8. F
9. F
10. T
129