48.
Which one of the following compounds is most acidic?
IIII
II IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
49.
Which one of the following compounds is most acidic?
H
N
NN
H
N
III III
A)
I
B)
II
C)
III
D)
I & III
E)
II & III
Ans:
C
Ans:
A
50.
Which one of the following compounds is most acidic? Explain your choice.
III
51.
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.
52.
Which one of the following compounds will undergo the fastest SN1 reaction?
Explain your choice.
Br
Br
IIII
II
Br
IV
Br
53.
Which one of the following compounds will undergo the fastest SN1 reaction?
Explain your choice.
III
Cl Cl
III
Cl
Ans:
I
The carbocation formed is aromatic and is more stable
54.
Provide the reagent(s) necessary to convert toluene to benzoic acid.
A)
Na2Cr2O7/H2SO4/H2O
B)
1. NBS,   a
C)
1. KMnO4/NaOH/H2O, 2. H3O+
D)
HNO3/H2SO4
E)
1. CO2, 2. H3O+
Ans:
A & C
Ans:
The carbocation formed is aromatic and is more stable
55.
Provide the product for the following reaction?
Na2Cr2O7/H2SO4/H2O
excess
COH
O
COH
COH
O
O
COH
O
CCH3
O
CH
CH
O
O
I II III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
B
56.
Provide the product for the following reaction?
Na2Cr2O7/H2SO4/H2O
excess
CCH3
O
CCH3
O
COH
O
COH
O
COH
O
CH
O
CH
O
I II III IV
O
VO
A)
I
B)
II
C)
III
D)
IV
E)
V
57.
Provide the product for the following reaction? Explain your answer.
1. KMnO4/NaOH/H2O
2. H3O+
excess
B
58.
Provide the structure of the major product(s) for the following reaction.
Cl2
h
Cl
Cl
Cl
Cl
Cl
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
Both I and II
Ans:
D
59.
Provide the structure of the major product(s) for the following reaction.
CH2CH2CH3
Br2
h
CH2CH2CH2Br
I
CH2CH2CH3
Br
II
CH2CHBrCH3
III
CH2CH2CH3
Br
IV
CHBrCH2CH3
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
E
60.
Provide the structure of the major product(s) for the following reaction.
I
IV
II
V
III
Cl2
Cl Cl
Cl
Cl
Cl
h
A)
I
B)
II
C)
III
D)
IV
E)
V
61.
Provide the structure of the major product(s) for the following reaction.
NBS
Ans:
E
62.
Provide the structure of the major product(s) for the following reaction.
NBS
63.
Provide the reagents necessary to carry out the following conversion.
NC
64.
Provide the reagents necessary to carry out the following conversion.
O
O
65.
Provide the reagents necessary to carry out the following conversion.
OCH3
66.
Provide the reagents necessary to convert ethylbenzene to styrene.
67.
Provide the reagents necessary to carry out the following conversion.
68.
Provide the reagents necessary to carry out the following conversion.
O
69.
Provide the structure(s) of the intermediate product(s) in the following reaction
sequence.
NBS
A(CH3)3COK B
1. BH3
2. H2O2/NaOH/H2O
CPCC D
70.
Provide the structure(s) of the intermediate product(s) in the following reaction
sequence.
NBS A(CH3)3COK B
CD
H2O/H2SO4Na2Cr2O7/H2SO4/H2O
71.
Predict the product for the following reaction.
NH3
Na, CH3OH
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
72.
Predict the product for the following reaction.
NH3
Na, CH3OH
O
III III IV V
OOOOO
A)
I
B)
II
C)
III
D)
IV
E)
V
73.
Predict the product for the following reaction.
OCH3
NH3
Na, CH3OH
OCH3OCH3
III
OCH3
III
OCH3
IV
OCH3
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
74.
Predict the product for the following reaction.
NH3
Na, CH3OH
75.
Predict the product for the following reaction.
NH3
Na, CH3OH
ONH2
76.
Predict the product for the following reaction.
NH3
Na, CH3OH
OCH3
H3CO
77.
Predict the product for the following reaction.
NH3
Na, CH3OH
O
78.
Provide stepwise synthesis for the following
O
79.
Provide stepwise synthesis for the following
H3CO
80.
Provide stepwise synthesis for the following
H
O
81.
The three isomers of dimethylbenzene are commonly named o—xylene, m—xylene,
p—xylene. These three isomers are difficult to distinguish using 1H NMR, but they can
be easily identified using 13C NMR.
Describe how 13C NMR distinguishes these three isomers.
82.
Which one of the following compounds would exhibit seven signals in its 13C NMR
spectrum?
OOOOO
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
83.
Which of the following isomer(s) of tribromoaniline will show two doublets with 7.5 Hz
coupling in 1HNMR spectrum?
NH2
Br
Br
Br
NH2
Br
Br
Br
NH2
Br
Br
Br
NH2
Br
BrBr
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
II & IV
Ans:
A
Ans:
C
84.
Provide a structure for the compound with molecular formula C9H9ClO and with the
following spectroscopic data.
IR: 1680 cm−1
1H NMR: 3.5 (triplet, I=2H), 4.0 (triplet, I=2H), 7.4 (triplet, I=2H), 7.6 (doublet,
I=1H), 7.9 (triplet, I=2H)
85.
Provide a structure for the compound with molecular formula C9H12 and with the
following spectroscopic data.
1H NMR: 1.2 (doublet, I=6H), 3.0 (septet, I=1H), 7.1 (singlet, I=5H)
86.
Provide a structure for the compound with molecular formula C10H12O2 and with the
following spectroscopic data.
IR: 1680 cm−1, 2750 cm−1, 2850 cm−1
1H NMR: 1.1 (triplet, I=3H), 3.5 (quartet, I=2H), 4.5 (singlet, I=2H), 7.3 (doublet,
I=2H), 7.7 (doublet, I=2H), 9.9 (singlet, I=1H)