Chapter Twenty Three

Topic: Classification of amines

Section: 23.1
Difficulty Level: Easy

1. Which of the following is a primary amine?

A) CH3CH2CH2CH2NH2
B) CH3CH2NHCH2CH(CH3)2
C) (CH3CH2)2NCH2CH(CH3)2
D) (CH3CH2)4N+ OH-
E) (CH3CH2)3N
Ans: A

Topic: Classification of amines

Section: 23.2
Difficulty Level: Easy

2. Which of the following is a secondary amine?

A) CH3CH2CH2CH2NH2
B) CH3CH2NHCH2CH(CH3)2
C) (CH3CH2)2NCH2CH(CH3)2
D) (CH3CH2)4N+ OH-
E) (CH3CH2)3CNH2
Ans: B

Topic: Classification of amines

Section: 23.1
Difficulty Level: Easy

3. Which of the following is a tertiary amine?

A) CH3CH2CH2CH2NH2
B) CH3CH2NHCH2CH(CH3)2
C) (CH3CH2)2NCH2CH(CH3)2
D) (CH3CH2)4N+ OH-
E) (CH3CH2)3CNH2
Ans: C

Topic: Classification of amines

Section: 23.1
Difficulty Level: Easy
 4. Which of the following is a quaternary ammonium salt?
A) CH3CH2CH2CH2NH3+ Cl-
B) (CH3CH2)2NH2+ Cl-
C) (CH3CH2)3NH+ Cl-
D) (CH3CH2)4N+ Cl-
E) none of these
Ans: D

Topic: Classification of amines

Section: 23.1
Difficulty Level: Medium

5. Classify the following compounds as a primary, secondary or tertiary amine.

H
NH2
N
N O

I II III
Ans: I-secondary amine
II-tertiary amine
III-primary amine

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Easy

6. 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

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium
 7. What is the common name for the following compound?

A) ethylethylisobutylamine
B) diethylisobutylamine
C) sec-butyldiethylamine
D) 2-diethylaminobutane
E) none of these
Ans: C

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

8. What is the common name for the following compound?

A) ethylisobutylisopropylamine
B) ethylisopropylbutylamine
C) sec-butylethylpropylamine
D) sec-butylethylisopropylamine
E) none of these
Ans: A

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

9. What is the common name for the following compound?

H
N

A) dibenzylamine
B) diphenylamine
C) dibenzeneamine
D) phenylbenzeneamine
E) none of these
Ans: B

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium
10. 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
Ans: B

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

11. What is the IUPAC name for the following compound?

A) N-cyclopentyl-N-methylcyclohexanamine
B) N-cyclohexyl-N-methylcyclohexanamine
C) N-cyclopentyl-N-methylcyclopentanamine
D) cyclohexylcyclopentylmethylamine
E) N-pentyl-N-methylhexanamine
Ans: A

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium
 12. 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

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

13. What is the IUPAC name for the following compound?

NH2

Ans: 5-cyclopropyl-1-heptanamine

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

14. What is the IUPAC name for the following compound?

NH2

Ans: (1S,2S)-2-methyl-1-cyclopentanamine

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

15. What is the structure for 3-chloro-N-ethylpentanamine?

Ans: H
N

Cl

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

16. What is the structure for N-ethylbenzylamine?

Ans:
N
H

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Medium

17. What is the structure for N,N-diethylaniline?

Ans:

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Hard

18. What is the IUPAC name for the following compound?

OH NH2

Ans: 7-amino-5-isopropyl-3-octanol

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Hard

19. What is the IUPAC name for the following compound?

NH2

HO

O
Ans: 4-amino-2,2-diethylhexanoic acid
Topic: Nomenclature of amines
Section: 23.2
Difficulty Level: Hard

20. What is the IUPAC name for the following compound?

HO

O NH2

Ans: 7-amino-5-ethyl-1-hydroxy-3-octanone

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Hard

21. What is the IUPAC name for the following compound?

O

NH2

Ans: 3-amino-4-ethylcyclohexanone

Topic: Nomenclature of amines

Section: 23.2
Difficulty Level: Hard

22. What is the IUPAC name for the following compound?

NH2

Ans: (1R,6R)-6-methylcyclohex-2-enamine

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium
 23. Arrange the following compounds in decreasing (highest to lowest) order of boiling
point.
CH3CH2CH2CH2NH2 CH3CH2N(CH3)2 CH3CH2CH2NHCH3
I II III
A) II>III>I
B) I>III>II
C) II>III>I
D) III>II>I
E) I>II>III
Ans: B

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium

24. Arrange the following compounds in decreasing (highest to lowest) order of boiling
point.
1-pentanol hexane 1-pentanamine butyl methyl ether
I II III IV
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

Topic: Properties of amines

Section: 23.3
Difficulty Level: Easy

25. Which of the following compounds is most soluble in water?

NH2
N N
H
II III
I
A) I
B) II
C) III
D) both I & II
E) all of these
Ans: B

Topic: Properties of amines

Section: 23.3
Difficulty Level: Easy
 26. Which of the following compounds is least soluble in water?
NH2
N N
H
II III
I
A) I
B) II
C) III
D) both I & III
E) none of these
Ans: C

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium

27. Arrange the following amines in decreasing (most to least) order of solubility in water.
NH2
N N
H
II III
I
A) III>I>II
B) I>III>II
C) I>II>III
D) II>I>III
E) III>II>I
Ans: D

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium

28. Which of the following compounds is the strongest base?

NH2 NH2 NH2 NH2
NH2

Cl
O2N IV V
I II III
A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium
 29. Rank the following compounds in decreasing (strongest to weakest) order of basicity.
NH2 NH2 NH2
NH2

O2N
II III IV
I
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
Ans: D

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium

30. Arrange the following compounds in decreasing (strongest to weakest) order of basicity.
CH3CH2NH2 (CH3CH2)3N NH3 (CH3CH2)2NH
I II III IV
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

Topic: Properties of amines

Section: 23.3
Difficulty Level: Hard

31. Arrange the following compounds in decreasing (strongest to weakest) order of basicity.
p-toluidine aniline p-nitroaniline p-methoxyaniline
I II III IV
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

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium
 32. Arrange the following compounds in decreasing (strongest to weakest) order of basicity.
O NH2
NH2 NH2 NH2

CF3 OCH3
IV
II III
I
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
Ans: E

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium

33. Arrange the following compounds in increasing (weakest to strongest) order of basicity.
NH2

H
N
NH2

NO2
I II III IV

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

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium
 34. Which one of the following is a stronger base? Explain why.

NH
N
I II H
Ans: I is a stronger base.
The nitrogen is connected to sp3C and the non bonding electrons on nitrogen are
not involved in resonance with the aromatic ring, whereas the nitrogen in II is
connected to sp2C and the non bonding electrons on nitrogen are delocalized over
the aromatic ring.

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium

35. Pyridoxamine, aka vitamin B6 has the following structure. Which nitrogen is more
basic? Explain your choice.
1

CH2NH2

HO CH2OH

H3C N

2
Ans: N1 is more basic as it is sp3 hybridized and is less electronegative because of less
s character, than the sp2 hybridized N2. The non bonding electrons are more easily
available in N1 than N2.

Topic: Properties of amines

Section: 23.3
Difficulty Level: Medium
 36. Nicotine present in tobacco has the following structure. Which nitrogen is more basic
and explain your choice.

N
2
CH3
N

1
Ans: N2 is more basic as it is sp3 hybridized and less electronegative because of less s
character.

Topic: Properties of amines

Section: 23.3
Difficulty Level: Hard

37. Chloroquine is used as an antimalarial drug. Rank the three nitrogen atoms in decreasing
(strongest to weakest) order of basicity.
III
I
N
HN

Cl N
II
A) III>I>II
B) I>III>II
C) I>IV>III>II
D) I>III>II>IV
E) III>II>I
Ans: E

Topic: Preparation of amines

Section: 23.4
Difficulty: Easy
 38. Predict the product for the following reaction.
CN H2/Ni

NH2
NH2 CN

I II III
O

NH2 NH

IV V
A) I
B) II
C) III
D) IV
E) V
Ans: B

Topic: Preparation of amines

Section: 23.4
Difficulty: Medium

39. Predict the product for the following reaction.

Br
1. NaCN
2. LiAlH4
3. H2O
CN NH2 NH2
NH2

III O
I II
IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: C

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Easy
 40. Provide the reagent(s) necessary to carry out the following conversion.
NO2 NH2

A) H2/Ni
B) 1. LiAlH4 2. H2O
C) Fe/HCl
D) NaBH4/CH3OH
E) all of these
Ans: C

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Medium

41. Predict the product for the following reaction.

O

NH2 1. LiAlH4

2. H2O

OH

NH2
NH2 NH2

I II III

H2N
H2N

O
OH
V
IV
A) I
B) II
C) III
D) IV
E) V
Ans A

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Medium
 42. Predict the product for the following reaction.
O

NH 1. LiAlH4

2. H2O

OH

O
NH NH

H2 N H2N
NH2
O
OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans A

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Medium

43. Provide the reagents necessary to carry out the following conversion for the following
reaction.
O

N N

Ans 1. LiAlH4
2. H2O

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Hard
 44. Predict the product for the following reaction sequence.

OH SOCl2 CH3NH2 1. LiAlH4

pyridine 2. H2O
O
Ans: H
N

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Hard

45. Provide the reagents necessary to convert (S)-3-methyl-3-phenylpentanoic acid to

(S)-3-methyl-3-phenylpentanamine.
Ans: 1. SOCl2/pyridine
2. NH3
3. LiAlH4
4. H2O

Topic: Preparation of amines

Section: 23.4
Difficulty Level: Medium

46. Provide the reagents necessary to carry out the following conversion.
CH2Br CH2CH2NH2

Ans: 1. NaCN
2. LiAlH4
3. H2O

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Easy
 47. Provide the reagents necessary to carry out the following conversion.
CH2CN CH2CH2NH2

Ans: 1. LiAlH4
2. H2O

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium

48. Predict the product for the following reaction.

Br 1. NaN3

2. LiAlH4
3. H2O

NHNH2 NH2 NNH2

N
NH

I II III IV
A) I
B) II
C) III
D) IV
E) III & IV
Ans: B

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium

49. Predict the product for the following reaction.

Br

1. NaN3

2. LiAlH4
3. H2O
Ans: NH2
Topic: Preparation of amines
Section: 23.5
Difficulty Level: Medium

50. Predict the product for the following reaction and provide a stepwise curved arrow
mechanism for the formation of the product.
1. LiAlH4
N3
2. H2O
Ans:
NH2

Mechanism
H
H
N AlH3
N
N N
N
N O
N
H H
H
+ N N
H Al H

H
NH2 + OH

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium

51. Predict the product for the following reaction sequence.

mCPBA NaN3 1. LiAlH4

2. H2O

OH N3 NH2 OH OH

NH2 OH OH NH2 N3
+ enantiomer + enantiomer + enantiomer + enantiomer + enantiomer
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Easy

52. 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

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium

53. Predict the product(s) for the following reaction.

O

1. KOH
NH
2. CH3CH2CH2CH2Br
+
3. H3O
O
O O

COH CNH2
NH2
+ NH2 +

COH COH

I II
O O

O O

CNH2

+ NH2 N

COH
III IV
O
O

A) I
B) II
C) III
D) IV
E) None of these
Ans: A

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium

54. Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.

O
Ans: O O

KOH Br N
NH NK

O O O
O

COH
H3O+
+

NH2
COH

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium

55. Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.

Ans: O O Br O

KOH N
NH NK

O O O
O

NH2 COH
H3O+
+

COH

Topic: Preparation of amines

Section: 23.5
Difficulty Level: Medium
 56. Predict the product for the following reaction.
O

+
KOH Br H3O
NH

O
Ans:

NH2

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Medium

57. Predict the product(s) for the following reaction.

O

NH2

H2SO4, NaBH3CN
NCH2CH3 NHCH2CH3
HO
NHCH2CH3

II III
I
O
H3CH2CHN
NHCH2CH3

N
IV V H
A) I
B) II
C) III
D) IV
E) V
Ans: B

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Medium
 58. Predict the product(s) for the following reaction.
NH2
O

H2SO4, NaBH3CN

N O HN
HO NH

III IV
I II
A) I
B) II
C) III
D) IV
E) None of these
Ans: D

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Hard

59. Provide the reagents necessary to carry out the following conversion.
H
N

Ans: O

1. CH3CCl / AlCl3
2. CH3CH2NH2, H2SO4, NaBH3CN

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Hard
 60. Provide the structures of the products in the following reaction sequence.

1. BH3 PCC (CH3)2NH

A B C
2. H2O2, NaOH/H2O H2SO4, NaBH3CN

Ans: B C
A

N(CH3)2
OH O N(CH3)2
+ enantiomer + enantiomer

N(CH3)2 N(CH3)2

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Hard

61. Provide the structures of the products in the following reaction sequence.
H
N

H3O+ PCC
A B C
H2SO4, NaBH3CN

Ans:

OH O N

A B C

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Hard
 62. Provide the reagents necessary to carry out the following conversion.

CN

O N
Ans: 1. HOCH2CH2OH/TsOH
2. H2/Pt
3. H3O+

Topic: Preparation of amines

Section: 23.6
Difficulty Level: Medium

63. Predict the product for the following reaction sequence.

Cl
(CH3)2NH

AlCl3 H2SO4, NaBH3CN

N
N O
N
O
OH
II
I III
IV

A) I
B) II
C) III
D) IV
E) none of these
Ans: D

Topic: Reactions of amines

Section: 23.8
Difficulty Level: Medium
 64. Provide the reagents necessary to carry out the following conversion.
Cl

Cl

NHCCH 2CH3

O
Ans: 1. Cl2/FeCl3
2. HNO3/H2SO4
3. Cl2/FeCl3
4. Fe/HCl
O

5. CH3CH2CCl

Topic: Reactions of amines

Section: 23.8
Difficulty Level: Medium

65. Provide the reagents necessary to carry out the following conversion.
NO2 NH2

Br
Ans: 1. Fe/HCl
O

2. CH3CCl
3. Br2/FeBr3
4. H3O+
5. dil. Na2CO3

Topic: Reactions of amines

Section: 23.9
Difficulty Level: Medium
 66. Predict the major product for the following reaction.
NH2
1. excess CH3I

2. Ag2O, H2O
heat
N(CH3)2 OH

I II III IV
A) I
B) II
C) III
D) IV
E) I & III
Ans: B

Topic: Reactions of amines

Section: 23.9
Difficulty Level: Medium

67. Predict the major product for the following reaction.

1. excess CH3I
NH2
2. Ag2O, H2O
heat

I II III
IV
A) I
B) II
C) III
D) IV
E) I & III
Ans: A

Topic: Reactions of amines

Section: 23.9
Difficulty Level: Hard
 68. Predict the major product for the following reaction.
1. excess CH3I

2. Ag2O, H2O
N heat

N N
N N
IV V
II III
I
A) I
B) II
C) III
D) IV
E) V
Ans: E

Topic: Reactions of amines

Section: 23.9
Difficulty Level: Hard

69. Predict the major product for the following reaction.

1. excess CH3I

2. Ag2O, H2O
N heat

Ans:

Topic: Reactions of amines

Section: 23.9
Difficulty Level: Medium
 70. Predict the major product for the following reaction.

1. excess CH3I
NH2
2. Ag2O, H2O
heat
Ans:

Topic: Reactions of amines

Section: 23.9
Difficulty Level: Medium

71. Provide the reagents necessary to carry out the following conversion.
O
NH2
O

A B C

HO

NH2

Ans: A. 1. NH3, 2. H2/Pt

B. 1. excess CH3I, 2. Ag2O, H2O
C. mCPBA
D. NH3

Topic: Reactions of amines

Section: 20.10 & 20.11
Difficulty Level: Easy
 72. Provide the reagents necessary to carry out the following conversion.
NO2 NO2

NH2 Cl
Ans: 1. NaNO2/HCl; < 50C
2. CuCl

Topic: Reactions of amines

Section: 20.10 & 20.11
Difficulty Level: Easy

73. Provide the reagent A, necessary to carry out the following conversion.
Br Br

NH2 OCH3
NaNO2/HCl A
0
<5 C

Br Br
A) H3PO2
B) HCN
C) H2O
D) CH3OH, heat
E) NaOCH3
Ans: D

Topic: Reactions of amines

Section: 20.10 & 20.11
Difficulty Level: Easy
 74. Provide the reagent A, necessary to carry out the following conversion.
Br Br

NH2
NaNO2/HCl A
0
<5 C

Cl Br Cl Br
A) Br2/FeBr3
B) CuBr
C) NaOH
D) H3PO2
E) H3PO4
Ans: D

Topic: Reactions of amines

Section: 20.10 & 20.11
Difficulty Level: Medium

75. Which one of the following is the best synthesis for 3,5-dibromotoluene?
A) toluene, Br2/FeBr3 excess
B) 1. p-toluidine, Br2/ FeBr3;
2. NaNO2/HCl, <5°C
3. H3PO2
C) 1. Toluene, HNO3/H2SO4
2. NH3
3. NaNO2/HCl, <5°C
4. CuBr
D) m-dibromobenzene, CH3Cl/AlCl3
E) m-bromotoluene, HNO3, H2SO4
2. Fe/HCl
3. NaNO2/HCl, <5°C
4. CuBr
Ans: B

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 76. Provide the reagents necessary to carry out the following conversion.
O

COH

Cl

F
Ans: 1. CH3CH2Cl/AlCl3
2. HNO3/H2SO4
3. Cl2/FeCl3
4. Fe/HCl
5. NaNO2/HCl/<50C
6. HBF4
7. Na2Cr2O7/H2SO4/H2O

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium

77. Provide the reagents necessary to carry out the following conversion.
OCH3

CCH2CH3

O
Ans: O

1. CH3CH2CCl / AlCl3
2. HNO3/H2SO4
3. Fe/HCl
4. NaNO2/HCl/<50C
5. CH3OH/heat

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 78. Provide the reagents necessary to carry out the following conversion.
OCH2CH3

Br
Ans: 1. HNO3/H2SO4
2. Br2/FeBr3
3. Fe/HCl
4. NaNO2/HCl/<50C
5. CH3CH2OH/heat

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium

79. Provide the reagents necessary to carry out the following conversion.
OH

NO 2
Ans: 1. HNO3/H2SO4
2. Fe/HCl
O

3. CH3CCl
4. HNO3/H2SO4
5. H3O+
6. NaNO2/HCl/<50C
7. H2O/heat

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 80. Provide the reagents necessary to carry out the following conversion.
OH

Ans:
N N Cl
NO2 NH2

HNO3/H2SO4 Sn/HCl NaNO2/HCl

<50C
OH OH

exess
H2O fuming H2SO4 (CH3)2CHCl/AlCl3


OH
SO3H OH

H3O+

SO3H

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 81. Provide the reagents necessary to carry out the following conversion.
O

COH

CN
Ans: CH2CH3 CH2CH3

CH3CH2Cl/AlCl3 HNO3/H2SO4 Na2Cr2O7/H2SO4/H2O

O O O O
NO2
COH COH COH COH

Fe/HCl NaNO2/HCl CuCN

0
<5 C

NO2 NH2 N N Cl CN

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 82. Provide the reagents necessary to carry out the following conversion.
O

NH2 COH

Br Br

CH3

Br
Ans:
N N Cl
NH2 NH2

Br Br Br Br

Br2/ FeBr3 NaNO2/HCl H3PO2

excess < 50 C
CH3 CH3
CH3

Br Br

Br Br
Br Br
1. KMnO4/NaOH/H2O

2. H3O+ O

CH3

Br OH
Br

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 83. Provide a stepwise synthesis to carry out the following conversion.
CH2NH2

O
Ans: NO2 NH2

CH3CH2CCl HNO3/H2SO4 Fe/HCl

AlCl3

O O
O

N N Cl CN CN

Zn(Hg)/HCl 1. LiAlH4
NaNO2/HCl CuCN
2. H3O+
0
<5 C

O O

CH2NH2

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 84. Provide a stepwise synthesis to carry out the following conversion.
I

Br Br

Ans: O

NO2 NH2 NHCCH3

O

HNO3/H2SO4 Sn/HCl CH3CCl fuming H2SO4

O
O

NHCCH3 NH2
NHCCH3

Br Br
excess Br Br
Br2/FeBr3 H3O+ NaNO2/HCl
heat <50C

N Cl SO3H
SO3H

N I

Br Br Br Br

CuI

Topic: Reactions of amines

Section: 23.10 & 23.11
Difficulty Level: Medium
 85. Provide the reagents necessary to carry out the following conversion.
NH2
Br

Br Br
Br Br

NO2
Ans: 1. NaNO2/HCl/<50C
2. CuBr
3. Fe/HCl
4. NaNO2/HCl/<50C
5. H3PO2

Topic: Reactions of amines

Section: 23.10 &23.11
Difficulty Level: Medium

86. Predict the major product for the following reaction.

OCH2CH3
CH3

NH2
NaNO2/HCl

2
< 50 C
Ans:
N

N OCH2CH3

CH3

Topic: Reactions of amines

Section: 23.10 &23.11
Difficulty Level: Hard

87. Predict the major product when p-toluidine reacts with sodium nitrite and hydrochloric
acid at <5C followed by o-ethylphenol?
2

Ans:
N

N OH
Topic: Reactions of amines
Section: 23.10 &23.11
Difficulty Level: Medium

88. Predict the major product for the following reaction.

N(CH3)2

NaNO2/HCl
NH2
< 50C
N(CH3)2 N(CH3)2

N
N
N N(CH3)2
N
I II
III

O2N N(CH3)2

2
IV
A) I
B) II
C) III
D) IV
E) None of these
Ans: B

Topic: Reactions of amines

Section: 23.10 &23.11
Difficulty Level: Medium

89. Predict the major product for the following reaction.

NaNO2/HCl 4-ethylphenol
4-chloroaniline
<50C
Ans:

N
N

OH
Cl

Topic: Reactions of amines

Section: 23.10 &23.11
Difficulty Level: Medium

90. Predict the major product for the following reaction.

CH3

N(CH3)2

N
N
Cl
CH3
Ans:

N
N

N(CH3)2

Topic: Reactions of amines

Section: 23.10 &23.11
Difficulty Level: Medium
 91. Provide the reagents necessary to carry out the following conversion.
Cl

N
N

OCH3
Cl
Ans: Cl Cl

Cl2/FeCl3 HNO3/H2SO4 Fe/HCl

Cl OCH3
Cl
NO2 NH2

NaNO2/HCl

< 50 C

N N Cl
N
N

OCH3

Topic: Nitrogen Heterocycles

Section: 23.12
Difficulty Level: Medium
 92. Predict the major product for the following reaction.
Br2

0 0C
N
H
Br

Br Br
N N N N N
H H H
V
III IV
I Br II Br
A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Nitrogen Heterocycles

Section: 23.12
Difficulty Level: Medium

93. Predict the major product for the following reaction.

Br2

0 0C
N
H
Br

Br
Br N
N N N N
H H H
III IV Br
I Br II V
A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Nitrogen Heterocycles

Section: 23.12
Difficulty Level: Medium
 94. Predict the major product when pyridine is treated with a mixture of nitric acid and
sulfuric acid.
A) 3-nitropyridine
B) 2-nitropyridine
C) 4-nitropyridine
D) 2,3-dinitropyridine
E) 4-aminopyridine
Ans: A

Topic: Spectroscopy
Section: 23.13
Difficulty Level: Medium

95. A compound with molecular formula C8H10BrN exhibits a singlet at 1.2 (I=2), a triplet
at 2.8 (I=2), a triplet at 3.0 (I=2), a doublet at 7.1 (I=2) and a doublet at 7.4 (I=2)
in its 1HNMR spectrum. Its IR spectrum shows two medium absorption bands near 3400
cm-1. What is the structure for this compound?
NH2 NH2
NH2 Br Br

NH2
Br

I Br
II III IV V
NH2
Br
A) I
B) II
C) III
D) IV
E) V
Ans: A

Topic: Spectroscopy
Section: 23.13
Difficulty Level: Medium

96. A compound with molecular formula C8H19N exhibits a triplet at 0.9 (I=6), a singlet at
1.1 (I=1), a sextet at 1.3 (I=4), a quintett at 1.4 (I=4) and a triplet at 2.6 (I=4) in
its 1HNMR spectrum. Its IR spectrum shows a medium absorption band near 3400 cm-1.
Its 13CNMR spectrum showed peaks at 13.7, 20.5, 30.4 and 49.2. What is the structure
for this compound?
Ans: H
N
Topic: Spectroscopy
Section: 23.13
Difficulty Level: Medium

97. A compound with molecular formula C4H11N exhibits a triplet at 0.9 (I=3), a doublet
at 1.1 (I=3), a quintet at 1.4 (I=2), a singlet at 1.7 (I=2) and a sextet at 2.8 (I=2)
in its 1HNMR spectrum. Its IR spectrum shows two medium absorption bands near
3400 cm-1. What is the structure for this compound?
Ans:

NH2

Topic: Spectroscopy
Section: 23.13
Difficulty Level: Hard

98. A compound with molecular formula C7H17N exhibits a triplet at 1.0 (I=3), a doublet
at 1.1 (I=6), a multiplet at 2.0 (I=1), a singlet at 2.3 (I=3), a doublet at 2.3 (I=2),
and a quartet at 2.4 (I=2) in its 1HNMR spectrum. Its 13CNMR spectrum showed
peaks at 13.4, 20, 27.9, 39.3, 49.5 and 65.2. What is the structure for this compound?
Ans:
N

Topic: Spectroscopy
Section: 23.13
Difficulty Level: Medium
 99. A compound with molecular formula C6H15N displays the following IR, 1H NMR and
13
C NMR spectra. Propose a structure for this compound.

SDBS
Ans: H
N

Topic: Spectroscopy
Section: 23.13
Difficulty Level: Hard
100. A compound with molecular formula C8H11N displays the following IR, 1H NMR and
13
C NMR spectra. Propose a structure for this compound.

140 120 100 80 60 40 20 0

PPM

SDBS
Ans: NH2