92.
Predict the product for the following reaction.
1. NaOCH3
3. H3O+
O
O O
2.
Br
O O
O
O
HO
OH
O
O
III III
O
IV
O
O
V
A)
I
B)
II
C)
III
D)
IV
E)
V
93.
Provide the reagents necessary to synthesize the following compound starting from
cyclohexanone.
O O
CN
Ans:
C
94.
Predict the product for the following reaction.
1. NaOCH33. H3O+
O
O O
2. O
O O
I
O O
OO II III
OO
IV
O O
V
O O
OHO
A)
I
B)
II
C)
III
D)
IV
E)
V
95.
Which one of the following compounds can be prepared using the Michael reaction?
O
O
O
OO
O
O
O
O
III V
HO
O O
III
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
C
Ans:
A
96.
Predict the product for the following reaction sequence.
1. NaOCH3H3O+
O
O O
2.
Br
1. NaOCH3
2. CH3CH2Br
1. LiAlH4
2. H3O+
HO HO
OH
HO
O
OH
HO
OH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
97.
Which of the following amines will form an enamine with aldehydes and ketones?
NH2
H
N
N
H
N
I II
III IV
A)
I
B)
II
C)
III
D)
IV
E)
II & III
98.
Which of the following amines will form an enamine with aldehydes and ketones?
N
HN
III III IV
N
H
N
A)
I
B)
II
C)
III
D)
IV
E)
I & III
Ans:
E
99.
Provide the reagents necessary to carry out the following conversion using Stork
enamine synthesis.
O O
O
100.
Predict the product for the following reaction.
O
(CH3)2NH
H2SO4
O
1.
2. H3O+
N(CH3)2O N(CH3)2O
O O
OHO
O OH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
101.
Predict the product for the following reaction.
(CH3)2NH
H2SO4
Cl
O
1.
2. H3O+
O
III III
IV V
O O N(CH3)2OO
Cl
O
OH
OH
O
O
O
A)
I
B)
II
C)
III
D)
IV
E)
V
102.
Provide the reactants necessary to synthesize the following compound using Stork
enamine synthesis.
H
O
O
Ans:
A
103.
Predict the product for the following reaction sequence.
O
(CH3)2NH O
O
1. LiAlH4
H2SO42. H3O+
1.
2. H3O+
104.
Predict the product for the following reaction.
O
O
O
+
NaOH
O
O
O O O
O
O
O
O
O
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
E
105.
Predict the product for the following reaction.
O
O
NaOH
+
O
O
O
III III IV
OH
O
A)
I
B)
II
C)
III
D)
IV
E)
II & IV
Ans:
B
106.
Provide the reactants necessary to prepare the following compound using Robinson
annulation.
O
O
O
O
OO
O
O
I II
+
+
OO
O
O
O
III
IV
++
A)
I
B)
II
C)
III
D)
IV
E)
I & III
Ans:
A
107.
Provide the reactants necessary to prepare the following compound using Robinson
annulation.
O
OO
O
OO
O
H
O
III III
IV
OO
V
+
+
+
+
+
A)
I
B)
II
C)
III
D)
IV
E)
V
108.
Provide the structures of the intermediates and the final product in the following
reaction sequence.
O
(CH3CH2)2NH
H2SO4
O
NaOH
1.
2. H3O+
XYZ
Ans:
E
109.
Provide the reagents necessary to carry out the following conversion.
H
O
O
O
110.
Provide the reagents necessary to carry out the following conversion.
H
O
111.
Provide the reagents necessary to carry out the following conversion.
H
OO
O
112.
Provide the structure of the reactant (X) necessary to carry out the following conversion.
O
O
H
O
NaOH
X
113.
Provide a stepwise synthesis for the following conversion.
H
O
Cl
O
114.
Which one of the following reaction sequences will yield 2,2-dimethylcyclohexane-1,3-
dione.
IO
O
O
O
O
III
II
IV
O
O
O
O
O
O
1. CH3MgBr
2. H3O+
excess 1. NaOCH3
2. H3O+
1. NaOCH3
2. H3O+
1. NaOCH3
2. H3O+
A)
I
B)
II
C)
III
D)
IV
E)
II & IV
Ans:
B
115.
Provide the reagents necessary to carry out the following conversion.
O
O
O
O
O
116.
Provide the reagents necessary to carry out the following conversion.
O O
O
O
O
O
O
117.
Using 1-propanol as your only source of carbon and using any other reagents of choice
provide a stepwise synthesis for the following conversion.
CH3CH2CH2OH CH3CH2CH2CHCH2OH
CH3
118.
Using 1-propanol as your only source of carbon and using any other reagents of choice
provide a stepwise synthesis for the following conversion.
CH3CH2CH2OH CH3CH2CH2CHCOCH2CH2CH3
CH3
O