Chapter fifteen (Aromatic Compounds)
1. Toluene is the common name for:
A)
B)
C)
D)
E)
Hydroxybenzene
Aminobenzene
Methylbenzene
Ethylbenzene
Methoxybenzene
Ans:
2. Anisole is the common name for:
A)
B)
C)
D)
E)
Hydroxybenzene
Aminobenzene
Methylbenzene
Ethylbenzene
Methoxybenzene
Ans:
3. Phenol is the common name for:
A)
B)
C)
D)
E)
Hydroxybenzene
Aminobenzene
Methylbenzene
Ethylbenzene
Methoxybenzene
Ans:
4. o-xylene is the common name for:
A)
B)
C)
D)
E)
Hydroxybenzene
Aminobenzene
1,2-dimethylbenzene
Ethylbenzene
1,3-dimethylbenzene
Ans:
5. What is the IUPAC name for the following compound?
OH
Br
A)
B)
C)
D)
E)
5-bromophenol
3-bromophenol
5-bromoaniline
3-bromoaniline
1-bromophenol
Ans:
6. Which of the following is another name for 4-chlorobenzaldehyde?
A)
B)
C)
D)
E)
o-chlorobenzaldehyde
m- chlorobenzaldehyde
p-chlorobenzaldehyde
styrene
1-chlorobenzaldehyde
Ans:
7. What is the IUPAC name for the following compound?
NH2
Br
NO2
A)
B)
C)
D)
E)
5-bromo-4-nitroaniline
5-bromo-p-nitroaniline
1-bromo-2-nitroaniline
3-bromo-4-nitroaniline
p-nitro-m-bromoaniline
Ans:
8. What is the correct structure for 4-amino-2-chlorophenol?
NO2
NO2
Cl
I
NH2
Cl
II
OH
OH
OCH3
Cl
Cl
III NH2
Cl
OH
IV
A)
B)
C)
D)
E)
NH2
CH
V
O
I
II
III
IV
V
Ans:
9. What is the correct order of the names for the following compound?
I
A)
B)
C)
D)
E)
II
III
I-naphthalene; II-triphenyl; III-biphenyl
I-naphthalene; II-phenanthrene; III-biphenyl
I-biphenyl; II-anthracene; III-naphthalene
I-naphthalene; II-anthracene; III-biphenyl
I-biphenyl; II- phenanthrene; III-naphthalene
Ans:
10. What is the IUPAC name for the following compound?
NH2
Cl
Cl
A)
B)
C)
D)
E)
3,4-dichloroaniline
2,4-dichloroaniline
2,5-dichloroaniline
3,6-dichloroaniline
2,6-dichloroaniline
Ans:
11. What is the IUPAC name for the following compound?
OH
A)
B)
C)
D)
E)
4-butylphenol
1-sec-butylphenol
4-propylphenol
4-sec-butylphenol
1-isobutylphenol
Ans:
12. What is the IUPAC name for the following compound?
NO2
COH
O
A)
B)
C)
D)
E)
6-ethyl-3-nitrobenzoic acid
1-ethyl-4-nitrobenzoic acid
2-ethyl-5-nitrobenzoic acid
2-ethyl-5-nitrobenzaldehyde
4-nitro-3-carboxyethylbenzene
Ans:
13. Draw is the structure for 1,3-diphenylbutane?
14. What is the structure for p-aminobenzoic acid (PABA)?
.
15. What is the IUPAC name for the following compound?
F
H
O
( 2-ethyl-4-fluoro-5-methylbenzaldehyde )
Ans:
16. What is the IUPAC name for the following compound?
NO2
H3CO
Cl
Ans:
(4-chloromethyl-2-nitroanisole)
.
17. What is the IUPAC name for the following compound?
Ans: .
18. What is the structure of styrene?
Ans:
19. What is the structure for 3-isobutyl-5-isopropylaniline?
NH2
Ans:
20. What is the structure for 4-amino-2-bromophenol?
OH
OH
Br
NH2
I
A)
B)
C)
D)
E)
Br
Br
Br
Br
H2N
II NH2
OCH3
OCH3
OH
III
IV
V
NH2
NH2
I
II
III
IV
V
Ans:
21. Which one of the following statement is not true for a compound to be
considered as aromatic?
A)
B)
C)
D)
E)
The compound must be cyclic and planar
The compound must be monocyclic.
The compound must have a conjugated system with p orbital at every vertex
The compound must satisfy Hückel’s rule –must have (4n + 2) electrons.
none of these
Ans:
22. Which one of the following compound is aromatic?
S
O
I
A)
B)
C)
D)
E)
I
II
III
IV
None of these
Ans:
II
III
IV
23. Which one of the following compound is aromatic?
II
I
A)
B)
C)
D)
III
IV
I
II
III
IV
Ans: C
24-Which one of the following compounds is most acidic?
H
N
H
N
II
I
I
II
III
I & III
II & III
A)
B)
C)
D)
E)
N
N
III
25. Which one of the following compounds is most acidic? Explain your
choice.
I
II
Ans: I.
The conjugate base of cyclopentadiene is aromatic and is more stable
26. Both pyridine and pyrrole are nitrogen containing aromatic
heterocyclic compounds. When treated with HCl, only pyridine forms
the hydrochloride salt, where as pyrrole is unreactive. Provide an
explanation for this observed reactivity.
N
H
N
Pyridine
Pyrrole
Ans: In pyridine, the non bonding electron pair on nitrogen is not part of the aromatic
sextet. So it is available for reaction with HCl, without disturbing the aromatic
stability.
In pyrrole, the non bonding electron pair on nitrogen is part of the aromatic sextet.
Being part of the aromatic sextet it is not available for reaction with HCl. If it
does react with HCl then it will form a cation that is non aromatic, thus disturbing
the aromatic stability.
.
27. Provide the product for the following reaction?
Na2Cr2O7/H2SO4/H2O
excess
O
COH
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
II
O
O
O
COH
CH
CCH3
COH
CH
CCH3
O
III
O
IV
O
O
V
O
28. Provide the product for the following reaction? Explain your answer.
excess
1. KMnO4/NaOH/H2O
2. H3O+
Ans:
COH
O
There is no hydrogen at the benzylic position with t-butyl group, so it does not
undergo oxidation.
29. Provide the structure of the major product(s) for the following
reaction.
Cl2
h
Cl
Cl
Cl
I
A)
B)
C)
D)
E)
I
II
III
IV
Both I and II
Ans: D
II Cl
III Cl
IV
30. Provide the structure of the major product(s) for the following reaction.
CH2CH2CH3
Br2
h
CH2CH2CH2Br
CH2CHBrCH3
CH2CH2CH3
CHBrCH2CH3
CH2CH2CH3
Br
I
A)
B)
C)
D)
E)
III
II Br
V
IV
I
II
III
IV
V
Ans: E
31. Provide the structure of the major product(s) for the following reaction.
Cl2
h
Cl
Cl
II
I
Cl
III
Cl
Cl
IV
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: E
V
32. Provide the structure of the major product(s) for the following reaction.
NBS

Ans:
Br
33. Provide the structure of the major product(s) for the following reaction.
NBS

Ans:
Br
34. Provide the reagents necessary to carry out the following conversion.
NC
Ans:
1. NBS/
2. NaCN
35. Provide the reagents necessary to carry out the following conversion.
O
O
Ans:
1. NBS/
O
2.
CH3CONa
36. Provide the reagents necessary to carry out the following conversion.
OCH3
Ans:
 NBS/
 CH3OH, 250C
37. Provide the reagents necessary to convert ethylbenzene to styrene.
Ans:
ethylbenzene
NBS

CH3CH2ONa
styrene
38. Provide the reagents necessary to carry out the following conversion.
Ans:
 NBS/
 CH3CH2ONa
39. Provide the reagents necessary to carry out the following conversion.
O
Ans:





NBS/
CH3CH2ONa
BH3
H2O2/NaOH/H2O
PCC
40. Provide the structure(s) of the intermediate product(s) in the following reaction
sequence.
NBS
A
(CH3)3COK

Ans:
1. BH3
PCC
C
B
O
Br
OH
A
D
2. H2O2/NaOH/H2O
B
C
H
D
41. Provide the structure(s) of the intermediate product(s) in the following reaction
sequence.
NBS
A
(CH3)3COK

Ans:
Br
H2O/H2SO4
C
B
HO
A
O
C
B
D
42. Predict the product for the following reaction.
Na, CH3OH
NH3
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
II
III
IV
Na2Cr2O7/H2SO4/H2O
V
D
43. Predict the product for the following reaction.
O
Na, CH3OH
NH3
A)
B)
C)
D)
E)
IV
III
II
I
O
O
O
O
O
V
I
II
III
IV
V
Ans: A
44. Predict the product for the following reaction.
OCH3
Na, CH3OH
NH3
OCH3
I
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
OCH3
OCH3
II
III
OCH3
OCH3
IV
V
45. Predict the product for the following reaction.
Na, CH3OH
NH3
Ans:
46. Predict the product for the following reaction.
O
NH2
Na, CH3OH
NH3
Ans:
O
NH2
48. Predict the product for the following reaction.
H3CO
OCH3
Na, CH3OH
NH3
Ans:
H3CO
OCH3
49. Predict the product for the following reaction.
O
Na, CH3OH
NH3
O
Ans:
50. Provide stepwise synthesis for the following
O
O
Ans:
Br
CH3CH2ONa
NBS

mCPBA
1. CH3MgBr, ether
2. H2O
HO
O
PCC
51. Provide stepwise synthesis for the following
H3CO
Ans:
Br
CH3CH2ONa
NBS
H3CO
H3CO

CH3OH
Na, CH3OH
H2SO4
NH3
52. Provide stepwise synthesis for the following
O
H
Ans:
Br
OH
NBS

O
H
.
CH3CH2ONa
1. BH3
2. H2O2/NaOH/H2O
PCC
CH2Cl2