Chapter 10 - Amines
Multiple Choice
Section: 10.1
Difficulty Level: Easy
1. Which is the classification of the following amine?
CH3
H3CCH2CH2CH2
a)
b)
c)
d)
N CH3 Cl
1°
2°
3°
4°
Section: 10.1
Difficulty Level: Medium
2. Procaine is a local anesthetic drug. What is the classification of the amines I and II?
O
I
N
O
procaine
II
NH2
a) I: primary aliphatic; II: primary aromatic
b) I: tertiary aliphatic, II: primary aromatic
c) I: tertiary aliphatic, II: tertiary aromatic
d) I: tertiary aromatic, II: tertiary aliphatic
197
Chapter 10 - Amines
Section: 10.1
Difficulty Level: Medium
3. Dopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and
invertebrates. What is the classification of the amine?
HO
HO
NH2
dopamine
a)
b)
c)
d)
primary aromatic
primary aliphatic
secondary aromatic
tertiary aliphatic
Section: 10.1
Difficulty Level: Medium
4. Hydrocodone is a semi-synthetic opioid, which is an orally active narcotic analgesic (painkiller), often
found (together with acetaminophen (N-(4-hydroxyphenyl)acetamide)) in Vicodin and other brands. What
is the classification of the amine?
N
O
O
O
hydrocone
a) tertiary aromatic
b) tertiary aliphatic
c) secondary aliphatic
d) primary aliphatic
198
Chapter 10 - Amines
Section: 10.2
Difficulty Level: Easy
5. Which is the correct structure for diphenylamine?
NH2
H
N
I
II
CH2
NH2
NH2
III
a)
b)
c)
d)
IV
I
II
III
IV
Section: 10.2
Difficulty Level: Easy
6. Which is the IUPAC name for the following structure?
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
199
Chapter 10 - Amines
Section: 10.2
Difficulty Level: Easy
7. Which is the structure for N,N-dimethyl-3-hexanamine?
N
N
I
II
N
N
III
a)
b)
c)
d)
IV
I
II
III
IV
200
Chapter 10 - Amines
Section: 10.2
Difficulty Level: Medium
8. Which pairs of names and structures match correctly?
I. piperidine
NH
NH
II. pyrrole
III. cyclohexylamine
IV. prrolidine
NH2
NH
V. pyridine
N
a) I and II and III
b) II and IV and IV
c) II and IV and V
d) I and III and V
Section: 10.2
Difficulty Level: Medium
9. Which is the name for the following compound?
NH3 Cl
a) aniline hydrochloride
b) phenyltrihydrogenammonium chloride
c) aniline chloride
d) benzylammonium chloride
201
Chapter 10 - Amines
Section: 10.2
Difficulty Level: Medium
10. Which is the name for the following compound?
O
H2N
a)
b)
c)
d)
COH
4-carboxy aniline
1-amino-4-carboxybenzene
benzylamine carboxylic acid
4-aminobenzoic acid
Section: 10.3
Difficulty Level: Hard
11. Arrange the amines in order of increasing boiling point (lowest first).
CH2CH3
CH3CH2
N
CH2CH3
CH2CH3
I
a)
b)
c)
d)
CH3CH2NH2
CH3CH2NH
II
III
II, III, I, IV
III, I, IV, II
IV, II, III, I
IV, III, I, II
202
CH3CH2NH3 Cl
IV
Chapter 10 - Amines
Section: 10.3
Difficulty Level: Hard
12. Arrange the amines in order of increasing boiling point (lowest first).
NH2
NH2
NH2
NH2
F
F
F
I
a)
b)
c)
d)
II
III
IV
I, III, II, IV
II, IV, I, III
IV, II, III, I
II, III, IV, I
Section: 10.3
Difficulty Level: Medium
13. Arrange the amines in order of increasing boiling point (lowest first).
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
Section: 10.3
Difficulty Level: Medium
14. Arrange the amines in order of increasing solubility in water (least first).
CH2CH3
CH3CH2
N
CH2CH3
CH2CH3
I
a)
b)
c)
d)
CH3CH2NH2
II
CH3CH2NH
III
II, III, I, IV
IV, II, III, I
IV, III, II, I
I, III, II, IV
203
CH3CH2NH3 Cl
IV
Chapter 10 - Amines
Section: 10.3
Difficulty Level: Medium
15. Arrange the amines in order of increasing solubility in water (least first).
H
N
H
N
Cl
Cl
I
Cl
II
H
N
H
N
Cl
III
IV
a) III, I, IV, II
b) II, I, III, IV
c) I, III, IV, II
d) IV, II, III, I
Section: 10.3
Difficulty Level: Medium
16. Arrange the following in order of increasing strength of the hydrogen bonds (weakest first).
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
204
Chapter 10 - Amines
Section: 10.3
Difficulty Level: Hard
17. Arrange the basicities of the four amines in decreasing order (highest first).
NH2
NH2
N
NH
I
II
III
a) II, III, I, IV
b) IV, III, II, I
c) I, III, IV, II
d) III, IV, I, II
205
IV
Chapter 10 - Amines
Section: 10.3
Difficulty Level: Hard
18. Order the following bases according to increasing basicity (weakest base first):
H
N
H
N
I
Cl II
H
N
H
N
F
IV
III
F
a) I, III, II, IV
b) III, II, IV, I
c) IV, II, III, I
d) II, IV, I, III
Section: 10.4
Difficulty Level: Medium
19. Which compound is the strongest base?
CH3
CH3
NH2
I
CH3
NH
II
CH3
CH3
N
III
a) I
b) II
c) III
d) IV
206
CH3
CH3
CH3
N
IV
OH
Chapter 10 - Amines
Section: 10.4
Difficulty Level: Medium
20. Which compound is the strongest base?
NH2
I
NH2
NH2
NH2
Br
NO2
CH3
II
III
IV
a) I
b) II
c) III
d) IV
Section: 10.4
Difficulty Level: Medium
21. Arrange the amines in order of increasing basicity (weakest first).
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
Section: 10.4
Difficulty Level: Hard
22. At pH 5.0, the ratio of morpholine and morpholinium ion is 1:1622. Which is the pK b of morpholine?
a)
b)
c)
d)
3.21
5.79
8.21
9.25
207
Chapter 10 - Amines
Section: 10.4
Difficulty Level: Hard
23. Guanidine has a pKb value of 0.4. Which is the ratio of guanidine to its conjugate acid at blood pH of
7.4?
a)
b)
c)
d)
10-6.2:1
10+6.2:1
1:1
2.5:1
Section: 10.4
Difficulty Level: Hard
24. When the following compounds are dissolved in water at the same concentrations, which one will have
the lowest pH (i.e., most acidic)?
CH3
CH3
CH2 N
CH2 N
CH3
II
I
CH3
CH2 N
CH3 OH
CH3
CH3
CH3 Cl
CH2 N
H
CH3
III
IV
a) I
b) II
c) III
d) IV
208
CH3 Cl
Chapter 10 - Amines
Section: 10.5
Difficulty Level: Medium
25. Which are the correct positions for the site of protonation of the bases, guanidine and imidazole?
NH
I
H2N
C
N
III
NH2
N
H
II
a)
b)
c)
d)
IV
I, III
II, IV
I, IV
II, III
Section: 10.5
Difficulty Level: Medium
26. 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?
H3C
a)
b)
c)
d)
CH3
N
OH
I
II
H3C
CH
III
I
II
III
None of the above
209
CH3
Chapter 10 - Amines
Section: 10.5
Difficulty Level: Medium
27. Which reactions will proceed predominately to products as written?
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)
NH3
I, II
III, IV
II, IV
I, III
210
CH3NH3 +
NH2
Chapter 10 - Amines
Section: 10.6
Difficulty Level: Easy
28. Which is the product of the following reaction?
NO2
Fe, HCl
ethanol/water
CH3
CH3
NO2
HOOC
NH3+ Cl-
COOH
CH3
I
CH3
II
NO2
Cl
CH3
CH3
Cl
CH3
III
CH3
IV
a) I
b) II
c) III
d) IV
211
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Medium
29. Which is the product of the following reaction?
NH2
NaNO2
HCl/water 0oC
CH3
N
NH2
O2N
N Cl
NH2
NO2
O2N
CH3
I
CH3
II
NO2
CH3
CH3
III
IV
a) I
b) II
c) III
d) IV
212
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Medium
30. Trinitrotoluene (TNT) reacts with large quantities of hydrogen in the presence of a nickel catalyst.
Which reaction product is formed?
O2N
NO2
H2 / Ni
H2O
NO2
O2N
NO2
NO2
H2N
NH2
NH2
I
II
H2N
NH2
NH2
IV
III
a)
b)
c)
d)
I
II
III
IV
213
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Hard
31. Adenosine reacts with sodium nitrite (food additive, for instance in bacon) in acidic aqueous solution.
The loss of dinitrogen (N2) is observed. What is the main structure formed in this reaction?
N
N
OH
O
H2N
N
NaNO2 / H+
OH
N
H2O
HO
adenosine
N
NO2
N
H2 N
O
N
OH
N
I
N
N
H
N
N
HO
O
N
OH
OH
N
II HO
OH
OH
N
N
HO
HO
O
III
OH
HN
N
O
O
N
OH
OH
N
HO
IV
a) I
b) II
c) III
d) IV
214
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Hard
32. Which of the starting materials forms a stable product with the molecular formula C9H11N after a)
hydrogenation with H2/Ni and b) a subsequent SN2-reaction (loss is HBr)? (10.7, HARD)
Br
Br
NO2
I
II
NO2
Br
Br
NO2
III
a)
b)
c)
d)
NO2
IV
I
II
III
IV
215
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Hard
33. Which is the product of the following reaction?
NH2
HPO2
NaNO2
HCl/water 0oC
CH3
NH3+Cl-
NH2
O2P
CH3
I
CH3
PO2
CH3
CH3
NO2
III
IV
II
a) I
b) II
c) III
d) IV
216
Chapter 10 - Amines
Section: 10.1
Difficulty Level: Medium
34. Which structures are secondary amines?
CH3
NCH3
CH3CHCH2NH2
H
I
II
NH
NH2
III
a)
b)
c)
d)
IV
I, II
II, III
III, IV
II, IV
Fill in the Blank Questions
Section: 10.2
Difficulty Level: Easy
1. The name of the following compound is ______________________________.
Br
N
H
217
Chapter 10 - Amines
Section: 10.2
Difficulty Level: Medium
2. The name of the following compound is _________________________________.
N
+
N Cl-
CH3
Section: 10.2
Difficulty Level: Medium
3. The name of the following compound is _______________________________.
CH3
N
H
CH3
Section: 10.4
Difficulty Level: Medium
4. The order of decreasing basicity of the following amines is (1 is the most basic),
CH3
O2N
NH2
N
H3C
218
N
CH3
H3C NH2
Chapter 10 - Amines
Section: 10.4
Difficulty Level: Medium
5. The order of increasing basicity of the following compounds is (1 is the least basic),
CH3
OH
O
NH2
OH
Section: 10.4
Difficulty Level: Medium
6. The order of increasing boiling point of the following compounds is (1 is lowest boiling),
CH3
OH
O
NH2
OH
Section: 10.6
Difficulty Level: Medium
7. The starting material needed to complete the following reaction is,
NH2
Fe, HCl
Br
219
Br
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Medium
8. The starting material needed to complete the following reaction is,
H3PO2
CH3
H3C
CH3
Section: 10.7
Difficulty Level: Medium
9. The major product of the following reaction is,
NH2
1) NaNO2, HCl, H2O, 0° C
O
2) warm solution
OH
Section: 10.7
Difficulty Level: Medium
10. The reactants and solvents needed to complete the following reaction are?
O
O
N
NO2
N
220
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Medium
11. The reactants and solvents needed to complete the following reaction are?
N
N
Cl
Cl
Cl
Section: 10.7
Difficulty Level: Hard
12. The reactants needed to complete the following reaction are,
NH2
OH
True-False Questions
Section: 10.1
Difficulty Level: Easy
1. Cyclohexanamine is a 2º amine.
Section: 10.1
Difficulty Level: Easy
2. tert-butyl methyl amine is a 3º amine.
Section: 10.2
Difficulty Level: Easy
3. The name of the following compound is N-cyclopentylethanamine.
H
N
CH2CH3
221
Chapter 10 - Amines
Section: 10.2
Difficulty Level: Medium
4. The name of the following compound is 3,5-dimethylpiperidine.
H
N
H3C
CH3
Section: 10.4
Difficulty Level: Easy
5. The strongest base in the following group is aniline.
NH2
NH2
N
Section: 10.4
Difficulty Level: Medium
6. The strongest base in the following group is methylthiocyclohexane.
HN
CH3
O
CH3
S
CH3
Section: 10.4
Difficulty Level: Medium
7. The pKa for ethyl ammonium ion is 10.8 (ethyl amine pK b is 3.2).
Section: 10.4
Difficulty Level: Medium
8. Tertiary amines are generally stronger bases than secondary amines.
Section: 10.5
Difficulty Level: Medium
9. The equilibrium for the reaction of p-nitroaniline and acetic acid lies to the right.
Section: 10.7
Difficulty Level: Easy
10. The diazotization of amines with NaNO2 requires a basic aqueous medium.
222
Chapter 10 - Amines
Section: 10.7
Difficulty Level: Medium
11. The reaction of aniline with nitrous acid after warming yields phenol.
223
Chapter 10 - Amines
Answers
Multiple Choice
1. d
2. b
3. b
4. b
5. b
6. c
7. b
8. d
9. a
10. d
11. a The boiling points are I 89°C, II 17°C, III 56°C, and IV > 200oC (ionic solid).
12. d
13. b
14. d
15. b
16. b
17. a
18. c
19. b
20. d
21. c
22. b
23. a
24. c
25. a
26. a
27. c
28. b
29. c
30. b
31. b
32. a
33. c
34. d
Fill in the Blank Questions
1. 3-bromopiperidine
2. 3-methylbenzenediazonium chloride
3. N-methyl 2-methylcyclohexanamine
4. 4, 3, 2, 1
5. 1, 3, 4, 2
6. 1, 3, 2, 4
224
Chapter 10 - Amines
7.
NO2
Br
Br
8.
N
+
N Cl-
9.
OH
HO
O
10.
H2 / Ni
O
NO2
NaNO2 / HCl
O
O
H2O
NH2
N
H2O
N
Cl
11.
225
Chapter 10 - Amines
N
N
H3PO2 / HCl
Cl
Cl
H2O
Cl
12.
1) NaNO2, H2O, HCl, O°
2) warm
True-False Questions
1. F
2. F
3. F
4. T
5. F
6. F
7. T
8. F
9. F
10. F
11. T
226