Chapter 10 - Amines

Multiple Choice

Section: 10.1
Difficulty Level: Easy
1. Which is the classification of the following amine?

a) 1°
b) 2°
c) 3°
d) 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
II

procaine 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

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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) primary aromatic
b) primary aliphatic
c) secondary aromatic
d) 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 O
hydrocone
a) tertiary aromatic
b) tertiary aliphatic
c) secondary aliphatic
d) primary aliphatic

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Section: 10.2
Difficulty Level: Easy
5. Which is the correct structure for diphenylamine?

NH2
H
N

I II

CH2
NH2

NH2
III IV
a) I
b) II
c) III
d) IV

Section: 10.2
Difficulty Level: Easy
6. Which is the IUPAC name for the following structure?

a) N-methyl-tert-butylamine
b) N-methyl-1,1-dimethylethylamine
c) N-methyl-2-methyl-2-propanamine
d) tert-butyl methyl amine

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Section: 10.2
Difficulty Level: Easy
7. Which is the structure for N,N-dimethyl-3-hexanamine?

N N

I II

N N

III IV

a) I
b) II
c) III
d) IV

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Section: 10.2
Difficulty Level: Medium
8. Which pairs of names and structures match correctly?

I. piperidine NH

II. pyrrole NH

III. cyclohexylamine NH2

IV. prrolidine
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?

a) aniline hydrochloride
b) phenyltrihydrogenammonium chloride
c) aniline chloride
d) benzylammonium chloride

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Section: 10.2
Difficulty Level: Medium
10. Which is the name for the following compound?

a) 4-carboxy aniline
b) 1-amino-4-carboxybenzene
c) benzylamine carboxylic acid
d) 4-aminobenzoic acid

Section: 10.3
Difficulty Level: Hard
11. Arrange the amines in order of increasing boiling point (lowest first).

a) II, III, I, IV
b) III, I, IV, II
c) IV, II, III, I
d) IV, III, I, II

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Section: 10.3
Difficulty Level: Hard
12. Arrange the amines in order of increasing boiling point (lowest first).

NH2 NH2 NH2 NH2

F
F

I II III IV

a) I, III, II, IV
b) II, IV, I, III
c) IV, II, III, I
d) II, III, IV, I

Section: 10.3
Difficulty Level: Medium
13. Arrange the amines in order of increasing boiling point (lowest first).

methylamine ethylamine propylamine cyclohexylamine

I II III IV

a) IV, III, II, I

b) I, II, III, IV
c) III, II, I, IV
d) II, I, IV, III

Section: 10.3
Difficulty Level: Medium
14. Arrange the amines in order of increasing solubility in water (least first).

a) II, III, I, IV
b) IV, II, III, I
c) IV, III, II, I
d) I, III, II, IV

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Section: 10.3
Difficulty Level: Medium
15. Arrange the amines in order of increasing solubility in water (least first).

H H
N N

Cl Cl Cl
I II

H H
N 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).

a) I, II, III, IV
b) II, I, IV, III
c) II, IV, I, III
d) I, IV, II, III

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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 IV

a) II, III, I, IV
b) IV, III, II, I
c) I, III, IV, II
d) III, IV, I, II

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Section: 10.3
Difficulty Level: Hard
18. Order the following bases according to increasing basicity (weakest base first):

H H
N N

I Cl II

H H
N F N

III IV
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 CH3

CH3 NH2 CH3 NH CH3 N CH3 CH3 N OH

I II III IV
a) I
b) II
c) III
d) IV

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Section: 10.4
Difficulty Level: Medium
20. Which compound is the strongest base?
NH2 NH2 NH2 NH2

Br NO2 CH3

I 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).

a) IV, II, III, I

b) II, I, III, IV
c) I, II, III, IV
d) 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) 3.21
b) 5.79
c) 8.21
d) 9.25

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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) 10-6.2:1
b) 10+6.2:1
c) 1:1
d) 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 CH3 CH2 N CH3 OH

CH3
I II

CH3 CH3
CH2 N CH3 Cl CH2 N CH3 Cl
H CH3

III IV
a) I
b) II
c) III
d) IV

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Section: 10.5
Difficulty Level: Medium
25. Which are the correct positions for the site of protonation of the bases, guanidine and imidazole?

a) I, III
b) II, IV
c) I, IV
d) 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?

a) I
b) II
c) III
d) None of the above

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Section: 10.5
Difficulty Level: Medium
27. Which reactions will proceed predominately to products as written?

a) I, II
b) III, IV
c) II, IV
d) I, III

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Section: 10.6
Difficulty Level: Easy
28. Which is the product of the following reaction?

NO2
Fe, HCl

ethanol/water
CH3 CH3

NO2 NH3+ Cl-

HOOC COOH CH3 CH3

I II

NO2
Cl Cl

CH3 CH3 CH3 CH3

III IV
a) I
b) II
c) III
d) IV

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Section: 10.7
Difficulty Level: Medium
29. Which is the product of the following reaction?

NH2

NaNO2

HCl/water 0oC

CH3 N
NH2 N Cl NH2
O2N NO2

O2N NO2
CH3 CH3 CH3 CH3

I II III IV

a) I
b) II
c) III
d) IV

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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 H2N NH2

NO2 NH2

I II

H2N NH2

NH2 IV
III

a) I
b) II
c) III
d) IV

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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 NaNO2 / H+
H2N N
OH H2O
N
HO

adenosine

NO2
N N OH N N
O OH
O
H2 N N HO
OH N
N OH
N
HO
I II HO

N N OH HN N
O OH
O
H N O
OH N
N OH
N
HO HO
III IV

a) I
b) II
c) III
d) IV

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Section: 10.7
Difficulty Level: Hard
32. Which of the starting materials forms a stable product with the molecular formula C 9H11N after a)
hydrogenation with H2/Ni and b) a subsequent SN2-reaction (loss is HBr)? (10.7, HARD)

Br
Br

NO2
NO2
I II

Br Br

NO2 NO2
III IV

a) I
b) II
c) III
d) IV

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Section: 10.7
Difficulty Level: Hard
33. Which is the product of the following reaction?

NH2

NaNO2 HPO2

HCl/water 0oC

CH3

NH3+Cl- NH2 CH3

O2P PO2
CH3 CH3 CH3 NO2

I II III IV

a) I
b) II
c) III
d) IV

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Section: 10.1
Difficulty Level: Medium
34. Which structures are secondary amines?

a) I, II
b) II, III
c) III, IV
d) II, IV

Fill in the Blank Questions

Section: 10.2
Difficulty Level: Easy
1. The name of the following compound is ______________________________.

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 Chapter 10 - Amines

Section: 10.2
Difficulty Level: Medium
2. The name of the following compound is _________________________________.

Section: 10.2
Difficulty Level: Medium
3. The name of the following compound is _______________________________.

Section: 10.4
Difficulty Level: Medium
4. The order of decreasing basicity of the following amines is (1 is the most basic),

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 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),

Section: 10.4
Difficulty Level: Medium
6. The order of increasing boiling point of the following compounds is (1 is lowest boiling),

Section: 10.6
Difficulty Level: Medium
7. The starting material needed to complete the following reaction is,

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 Chapter 10 - Amines

Section: 10.7
Difficulty Level: Medium
8. The starting material needed to complete the following reaction is,

Section: 10.7
Difficulty Level: Medium
9. The major product of the following reaction is,

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

O
O

N
NO2
N

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 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,

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.

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 Chapter 10 - Amines

Section: 10.2
Difficulty Level: Medium
4. The name of the following compound is 3,5-dimethylpiperidine.

Section: 10.4
Difficulty Level: Easy
5. The strongest base in the following group is aniline.

Section: 10.4
Difficulty Level: Medium
6. The strongest base in the following group is methylthiocyclohexane.

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.

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 Chapter 10 - Amines

Section: 10.7
Difficulty Level: Medium
11. The reaction of aniline with nitrous acid after warming yields phenol.

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 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

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7.

8.

9.

10.

H2 / Ni NaNO2 / HCl
O
O O

H2O H2O N
NO2 NH2
N
Cl

11.

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 Chapter 10 - Amines

N H3PO2 / HCl
N
Cl
Cl H2O Cl

12.

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

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