43.
Predict the product for the following conversion.
O
O
O
H3O+
1 mol
44.
Predict the product for the following reaction.
HO
O
H
H2SO4
O
OH
O
OH
O
OH
O
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
45.
Predict the product for the following reaction.
O
CH3CH2OH
H2SO4
excess
HO OH O OH O O
O OH O O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
46.
Predict the product(s) for the following reaction.
H3O+
O
O
Ans:
C
47.
Predict the product for the following reaction.
O
H
H2SO4
OH
O
OH
O
OH
O
O
O
OH
III III V
IV
OH
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
48.
Predict the product for the following reaction.
H3O+ excess
H3CO OCH3
III III IV
HO OCH3HO OH O
OH
HO
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
C
49.
Predict the product for the following reaction and provide a curved arrow mechanism
for the formation of the product.
HOCH2CH2OH
H2SO4
O
50.
Predict the product for the following reaction
H3O+
O
O
O
O
OH
HO
OH
HO
O
H
OH
HO
H
O
OH
HO
O
OH
HO
III III
IV V
+ ++
++
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
51.
Which one of the following pairs of compounds will yield the following product in
presence of sulfuric acid?
O
O
O
O
OH
HO
OH
HO
O
H
OH
HO
H
O
OH
HO
O
OH
HO
III III
IV V
+ ++
++
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
C
52.
Predict the product, when pentanal reacts with methanamine in presence of acid catalyst.
H
NCH3
HO
NHCH3
H
NHCH3
H3CHN
O
HO
CH2NH2
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
53.
Predict the product, when 4-methyl-2-hexanone reacts with hydrazine in presence of
acid.
NNH2
HO NHNH2
NHCH3
H2N
O
HO NH2
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
Ans:
B
54.
Predict the product for the following reaction.
O
NH2OH
H2SO4
NH2HO OH
ONH2NOH
III III IV
NHOH
V
HO
A)
I
B)
II
C)
III
D)
IV
E)
V
55.
Predict the product, when cyclopentanecarbaldehyde reacts with phenylhydrazine in
presence of acid catalyst.
HNNHPh HNNH2HNHNHPh HN
NPh
H2NO
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
Ans:
D
56.
Predict the product for the following reaction and provide a curved arrow mechanism
for the formation of the product.
NH2OH
H2SO4
H
O
57.
Predict the product for the following reaction.
O
NH2NHCNH2
O
H2SO4
II III
IV
NNHCNH2
O
NCNHNH2
O
HO NNHCNH2
O
CNHNH2
H2N
I
V
HO NHCNHNH2
O
A)
I
B)
II
C)
III
D)
IV
E)
V
58.
Provide the reagents necessary to carry out the following conversion.
NH2N
A)
propanone / H2SO4
B)
propanal/ H2SO4
C)
1-propanol/H2SO4
D)
2-propanol/ H2SO4
E)
Ethanal/ H2SO4
Ans:
B
Ans:
D
59.
Predict the product for the following reaction sequence.
CH2CH2OH
PCC (CH3)2NH
NN
OH
N
N
III
IV V
N
III
A)
I
B)
II
C)
III
D)
IV
E)
V
60.
Predict the product of the following reaction.
O
H
N
H2SO4
+
Ans:
B
61.
Predict the product of the following reaction.
NH2
NH2
O
O
+
H2SO4
62.
Provide the reactant(s) necessary to prepare the following compound.
N
63.
Provide the product for the following reaction
O
NH2NH2/ KOH
A)
3-methylhexane
B)
3-methyl-4-hexanol
C)
4-methyl-2-hexene
D)
3-methyl-4-hexene
E)
3-methyl-3-hexene
64.
Provide the product for the following reaction
1. NH2NH2, KOH
OH
O
O
2. H3O+
OH
NNH2
O
OH
O
NNH2
III
OH
O
III
NH2
O
O
OH
O
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
C
Ans:
A
65.
Which reagent(s) could NOT be used to carry out the following transformation?
O
A)
Zn(Hg), HCl
B)
LiAlH4, ether
C)
HSCH2CH2SH, BF3; then Raney Ni (H2)
D)
NH2NH2/KOH/heat
Ans:
B
66.
Predict the product for the following reaction.
CH
CH
O
O
NH2NH2, KOH
excess
CH
CH
NNH2
NNH2
CH3
CH3
CH
CH
NHNH2
HO
HO NHNH2
OH
OH
CNH2
CNH2
O
O
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
67.
Provide the reagents necessary to carry out the following conversion.
CH
CH
O
O
CH3
CH3
A)
NaBH4/CH3OH
B)
NH2NH2/KOH,
C)
H2/Ni
D)
1. LiAlH4 , 2. H2O
68.
Provide the major product for the following reaction sequence.
CH2CH3
CH3CH2CH2CCl
O
AlCl3
NH2NH2/ KOH
CH2CH3
CCH2CH2CH3
O
CH2CH3
CH2CH2CH2CH3
CH2CH3
CCH2CH2CH3
O
III III
CH2CH3
CH2CH2CH2CH3
V
CH2CH3
CCH2CH2CH3
H2NN
IV
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
Ans:
B
69.
Provide the product of the following reaction.
SH SH
H2SO4
+
propanal
S
HO
SH
S S S S
SSH
OH
III
III IV
A)
I
B)
II
C)
III
D)
IV
70.
Provide the product for the following reaction sequence.
CH2CH3
CH3CH2CH2CCl
O
AlCl3H2SO4
Raney Ni
HSCH2CH2SH
CH2CH3
CCH2CH2CH3
O
CH2CH3
CH2CH2CH2CH3
CH2CH3
CCH2CH2CH3
O
III III
CH2CH3
CH2CH2CH2CH3
V
CH2CH3
CCH2CH2CH3
HO
SCH2CH2SH
IV
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
Ans:
A
71.
Predict the product for the following reaction.
Oexcess
CH3CH2SH
H2SO4
72.
Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
O
H
O
H
OO
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
A
73.
What would be the product of the following reaction?
H
O
NaBH4/CH3OH
OH OH
OH
O
OH
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
74.
Predict the product for the following reaction sequence.
Cl
O
AlCl3
NaBH4/CH3OH
OOH
OCH3
OH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
Ans:
A