70.
Predict the product(s) for the following reaction.
O
1. LDA
2. CH3CH2Br
OOO O
III III IV
A)
B)

C)

D)
V
E)
none of these
Ans:
A
71.
Explain if the following reaction will yield the product shown.
1. NaH
O
2.
O
2-iodo-2-methylbutane
72.
Predict the product(s) for the following reaction.
O
O O
O O
O O
HO OH
O O
O
O
III
IV V
OH
O
III
A)
B)

C)

D)
V
E)
none of these
Ans:
D
73.
Predict the product(s) for the following reaction sequence.
1. NaOCH2CH3
2. CH3CH2I
O O
O O
H3O+
1. NaOCH2CH3
2. CH3CH2I
O O
O O
HO OH
O O
O
O
II
V
OH
O
III
IV
OH
O
I
A)
B)

C)

D)
V
E)
V
Ans:
D
74.
Predict the product(s) for the following reaction sequence.
1. NaOCH2CH3
2. CH3CH2I
O O
O O
H3O+
1. NaOCH2CH3
2. CH3I
CH3OH
H2SO4
O O
O O
HO OH
O O
II
V
I
OH
O
O O
O O
III
IV
O
O
A)
B)

C)

D)
V
E)
V
Ans:
D
75.
Predict the final product for the following reaction sequence.
malonic ester 1. sodium ethoxide
2. 1-bromopentane
1. sodium ethoxide
2. bromomethane
H3O+
A)
2-methylheptanoic acid
B)
3-methylhexanoic acid
C)
3-methylpentanoic acid
D)
2-methylpentanoic acid
E)
ethyl 2-methylheptanoate
Ans:
A
76.
Predict the product(s) for the following reaction sequence.
O O
O O
1. NaOCH2CH3
2.
H3O+
1. NaOCH2CH3
2.
Br
Br
OH
O
HO OH
O O
O
O
I
II
III
O
IV
O O
O O
V
A)
B)

C)

D)
V
E)
V
Ans:
A
77.
Provide the reagents necessary to carry out the following conversion using malonic ester
synthesis.
OH
O
O O
O O
78.
Predict the final product for the following reaction sequence.
O O
O O
1. NaOCH2CH3
2.
H3O+
NaOCH2CH3
Br
Br
O
HO
OH
O
HO
O
O
O
O
O
HO OH
O O
OH
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
C
79.
Predict the final product for the following reaction sequence.
O O
O O
1. NaOCH2CH3
2. Br(CH2)5Br
H3O+
NaOCH2CH3
OH
O
O
O
III III
IV V
OH
O
O
O
OH
O
HO O
OH
O
HO
O
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
C
80.
Provide the structures of the intermediates and the final product in the following
reaction sequence.
O O
O O
1. SOCl2
1. NaOCH2CH3
2.
H3O+
X
Br Y
2. AlCl3
Z
81.
Which of the following ketones cannot be prepared using acetoacetic ester synthesis?
O O O O
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
A & C
Ans:
D
82.
Predict the product for the following reaction sequence.
H3O+
O
O O
1. NaOCH2CH3
2. CH3CH2CH2I
O
O O
HO
O O
O
O
O
OH
III
V
IV
HO
O
III
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
83.
Predict the product for the following reaction sequence.
H3O+
O
O O
1. NaOCH2CH3
2. Br
O
O O
HO
O O
III
HO
O
III
O
O
O
OH
V
IV
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
84.
Predict the product for the following reaction sequence.
H3O+
O
O O
1. NaOCH2CH31. NaOCH2CH3
2. CH3CH2I
2. CH3CH2I
HOCH2CH2OH
H2SO4
III III V
IV
H
OO OO
OO
O
O
OO
HO
O
OO
A)
I
B)
II
C)
III
D)
IV
E)
V
85.
Provide the reagents necessary to carry out the following conversion.
O O
O
O O
A)
Cl
O
1. NaH
2.
3. H3O+
B)
1. NaOCH2CH33. H3O+
O
Br
2.
C)
1. NaOCH2CH33. H3O+
Br
2.
D)
1. NaOCH2CH33. H3O+
Br
2.
E)
all of these
Ans:
A
Ans:
C
86.
Provide the reagents necessary to prepare the following compound starting with
acetoacetic ester.
O
O
87.
Which one of the following nucleophiles will undergo conjugate addition in Michael
reaction?
O
CN
O
O
NH2
O
III III IV
(CH3CH2)2CuLi
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
E
88.
Which one of the following is the most reactive Michael acceptor?
O
NO2
O
O
NH2
O
III III IV V
CN
A)
I
B)
II
C)
III
D)
IV
E)
V
89.
Predict the product for the following reaction.
O
1. (CH3CH2CH2)2CuLi
2. H3O+
HO
O
O
OH
I II III
IV
A)
I
B)
II
C)
III
D)
IV
E)
I & IV
Ans:
A
Ans:
C
90.
Predict the product for the following reaction.
O
1. CH3CH2CH2MgBr
2. H3O+
HO
O
O
OH
I II III
IV
A)
I
B)
II
C)
III
D)
IV
E)
I & IV
Ans:
D
91.
Predict the product for the following reaction.
1. KOH
3. H3O+
O O
O
2.
O
OO
O
O
O
O
O
O
O
O
O
III
IV
III
HO
O
O
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B