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78.
Predict the product for the following reaction.
O
O
1. DIBAH
2. H2O
OH
OH
H
O
OH
O
OH
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
79.
Provide the reagents necessary to carry out the following conversion.
OCH3
O
HO
A)
1. (CH3)2CuLi 2. H2O
B)
1. excess DIBAH 2. H2O
C)
1. excess CH3MgBr 2. H2O
D)
Both A & C
E)
none of these
80.
Predict the product(s) for the following reaction.
CH2OC(CH2)14CH3
CHOC(CH2)16CH3
CH2OC(CH2)14CH3
O
O
O
NaOH excess
81.
Provide the reagents necessary to carry out the following conversion.
O
OHO COCH(CH3)2
O
82.
Barbitol, used as sedative, is synthesized from diethyl-2,2-diethyl malonate (A) and
urea(B). Provide the structure for Barbitol.
C
C
O
O
OCH2CH3
OCH2CH3
C
H2N
H2N
O
+
AB
83.
Predict the product for the following reaction sequence.
Br SOCl2
Mg/ether 1. CO2
2. H3O+Pyridine
exess
CH3NH2
O
NHCH3
NHCH3
O
O
O
NHCH3
III III
NHCH3
IV
O
NH2
V
A)
I
B)
II
C)
III
D)
IV
E)
V
84.
Predict the product for the following reaction
OH
C
O
NHCH3CH3COCCH3
OO
Excess
85.
Provide the reagents necessary to carry out the following conversion.
NH2
O
O
O O
86.
Provide the reagents necessary to carry out the following conversion.
H2N
O
O
O
87.
Predict the product for the following reaction
N
O
O
1. LiAlH4 (excess)
2. H3O+
N
OH
H
O
N
OH
H
HO
H
N
OH
H
N
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
I & II
88.
Aspartame is an artificial sweetener used in Equal and diet soft drinks. Predict the
product(s) for the following reaction.
H
N
O OCH3
O
NH2
COH
O
excess H3O+
Aspartame
89.
Provide the reagents necessary to carry out the following conversion.
O
O
N
OH
90.
Provide the reagents necessary to carry out the following conversion.
CN
A)
1. CH3Cl/AlCl3
2. Br2/h
3. NaCN
B)
1. CH3Cl/AlCl3
2. HCN
C)
1. Br2/FeBr3
2. Mg/ether
3. CO2
4. H3O+
5. excess NH3
6. SOCl2
D)
A & C
E)
A & B
91.
Predict the product(s) for the following reaction.
O
NH2
SOCl2
92.
Predict the product for the following reaction sequence.
OH
PCl3SOCl2
Na2Cr2O7/H2SO4/H2Oexcess
NH31. CH3CH2MgBr
2. H3O+
N
H
O
H
N
HO NH2
O
NH2
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
93.
Provide the reagents necessary to carry out the following conversion.
CN
O
94.
Provide the reagents necessary to carry out the following conversion.
CN
NH2
95.
Predict the product for the following reaction.
CN
H3O+
heat
96.
Predict the product for the following reaction and provide a stepwise curved arrow
mechanism for the formation of product.
CH3(CH2)3C
2. H3O+
1. CH3CH2Li
N
97.
Propose a stepwise synthesis for the following conversion.
Br
O
98.
Using ethyl-3-methylybutanoate as your only source of carbon and using any other
reagents necessary, propose a stepwise synthesis for the following conversion.
O
OHO
99.
Using ethyl-3-methylybutanoate as your only source of carbon and using any other
reagents necessary, propose a stepwise synthesis for the following conversion.
O
OO
100.
Propose a stepwise synthesis for N-propylbutaneamide, using 1-proanol and/or carbon
dioxide as your only source of carbon and using any other reagents necessary.
101.
Propose a stepwise synthesis for 2-phenylethanoyl chloride, using toluene and/or carbon
dioxide as your only source of carbon and using any other reagents necessary.
102.
A compound with molecular formula C6H12O2 exhibits two singlet in its 1HNMR
spectrum, at 1.4 (I=9) and 2.0 (I=3). Its IR spectrum shows a strong absorption band
near 1740 cm-1. What is the structure for this compound?
O
O
O
O
O
O
O
O
O H
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
103.
A compound with molecular formula C8H14O4 exhibits a triplet at 1.3 (I=6), a singlet
at 2.6 (I=4) and a quartet at 4.2 (I=4) in its 1HNMR spectrum. Its IR spectrum shows
a strong absorption band near 1740 cm-1. What is the structure for this compound?
O
O
O
O
O O
O O
O
O
O
OO
O
O
O
II
I
III
IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
104.
A compound with molecular formula C9H10O2 exhibits a triplet at 1.2 (I=3), a quartet
at 2.6 (I=2), a doublet at 7.3 (I=2), a doublet at 8.0 (I=2) and a singlet at 11 (I=1)
in its 1HNMR spectrum. What is the structure for this compound?
105.
A compound with molecular formula C8H14O3 exhibits a triplet at 1.0 (I=6), a sextet at
1.6 (I=4) and a triplet at 2.2 (I=4) in its 1HNMR spectrum. Its IR spectrum shows
two strong absorption bands near 1850 & 1750 cm-1. What is the structure for this
compound?
