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?

I
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?

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

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?

II

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

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

CH2CH3

I
a)
b)
c)
d)

CH2CH3
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

CH2CH3

I
a)
b)
c)
d)

CH2CH3
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

I
H
N

II

Cl

Cl

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

NH

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

Cl II

H
N

H
N

IV

III

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

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 pKb 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

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

NH2

III

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

CH3

I
a)
b)
c)
d)

OH

H3C

II

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

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

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

H 2N

OH

O
N

NaNO2 / H+

OH

H2O

HO
adenosine

NO2

H2N

O
N

N
I
N

OH

OH
OH

HO
III

HO

O
N

HO

OH

HN

OH

II HO

OH

O
N

OH
OH

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
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

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 _______________________________.

N
H

CH3

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

H 3C

218

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

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

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?

NO2

220

Chapter 10 - Amines

Section: 10.7
Difficulty Level: Medium
11. The reactants and solvents needed to complete the following reaction are?

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 2 amine.
Section: 10.1
Difficulty Level: Easy
2. tert-butyl methyl amine is a 3 amine.
Section: 10.2
Difficulty Level: Easy
3. The name of the following compound is N-cyclopentylethanamine.

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

CH3

CH3

Section: 10.4
Difficulty Level: Medium
7. The pKa for ethyl ammonium ion is 10.8 (ethyl amine pKb 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 TheboilingpointsareI89C,II17C,III56C,andIV>200oC(ionicsolid).
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
H2O

NH2

H2O
Cl

11.

225

Chapter 10 - Amines

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