75.
Provide the product of the following reaction.
NaBH4/CH3OH
O
OCH3
O
OH
OCH3
OO
OH
OH
OH
OH
OCH3
OH
I
II
III IV
A)
I
B)
II
C)
III
D)
IV
76.
Provide the reagents necessary to carry out the following conversion.
O
H
OOH
H
O
A)
NaBH4/CH3OH
B)
1. HOCH2CH2OH/H2SO4, 2. NaBH4/CH3OH, 3. H3O+,
C)
1. HOCH2CH2OH/H2SO4, 2.LiAlH4/ether, 3. H2O
D)
H3O+
Ans:
B
Ans:
A
77.
Predict the product for the following reaction sequence.
OH
PBr3H
O
PCC
Mg/ether
2. H3O+
1.
A)
6,7-dimethyl-3-nonanol
B)
6,7-dimethyl-3-nonanone
C)
6,7-dimethyl-3-nonanal
D)
3,4-dimethyl-7-nonanol
E)
3,4-dimethyl-7-nonanone
78.
The product, of the following reaction sequence,
OH
PBr3H
O
CrO3/ H2SO4/H2OMg/ether
2. H3O+
1.
A)
6,7-dimethyl-3-nonanol
B)
6,7-dimethyl-3-nonanone
C)
6,7-dimethyl-3-nonanal
D)
3,4-dimethyl-7-nonanol
E)
3,4-dimethyl-7-nonanone
Ans:
B
79.
Provide the reagents necessary to carry out the following conversion.
Br
O
Ans:
B
80.
Provide the reagents necessary to carry out the following conversion.
O
HO
A)
1. CH3CH2ONa, 2. H2O
B)
1. CH3CH2Br/Mg/ether, 2. H2O
C)
1. CH3CH2 CH2ONa, 2. H2O
D)
1. CH3CH2 CH2Br/Mg/ether, 2. H2O
Ans:
B
81.
Provide the product for the following reaction
Br
O
HOCH2CH2OH
O
H2SO4
Mg/ether
1.
2. H2O
H3O+
O
OH
O
O
O
OH
O
O
OH
O
O
O
O
HO OH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
82.
Provide the reagents necessary for the following conversion.
O
Br
CH2CH3O
CH2CH3
CH2CH3
A)
1. NaBH4/CH3OH, 2. CH3CH2MgBr
B)
CH3CH2MgBr/ether
C)
1. H3O+, 2. CH3CH2MgBr/ ether,
D)
1. CH3CH2MgBr/ ether, 2. H3O+,
83.
Which one of the following compounds will yield 1-hexanol when treated with
butylmagnesium bromide followed by acid workup?
A)
1-hexanol
B)
formaldehyde
C)
acetaldehyde
D)
oxirane
E)
hexanal
Ans:
D
Ans:
B
84.
Predict the product for the following reaction sequence:
H
O
MgBr
H2O
MgBr
H2O
ether
K2Cr2O7/H2SO4/H2O
ether
OH OHO
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
85.
Provide the reagents necessary to carry out the following conversion.
OH HO CN
Ans:
C
86.
Predict the product of the following reaction sequence,
O
NaCN
HCl
1. LiAlH4
2. H2O
H2N
O
HO NH2HO
H2N
H2N
HO CN
H2N
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
87.
Provide the reagents necessary to carry out the following conversion
O
OH
OH
O
88.
Provide the reactants necessary to prepare the following alkene using the Wittig
reaction.
A)
ethanal and 2-bromopentane
B)
propanal and 2-bromopentane
C)
2-pentanone and 1-bromopropane
D)
2-pentanone and 2-bromopropane
E)
butanal and 2-bromopentane
Ans:
C
89.
Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3-pentanone
using a Wittig reaction.
A)
Ph3P=CH(CH2CH3)2
B)
Ph3P=CHCH2CH3
C)
Ph3P=CHCH2CH2CH3
D)
Ph3P=CH2
E)
Ph3P=CHCH2(CH3) 2
Ans:
C
90.
Provide the structure of the reactant in the following reaction.
Ph3P=CHCH3
A)
cyclohexanone
B)
cyclohexanecarbaldehyde
C)
cyclohexylpropanone
D)
3-cyclohexylpropanal
Ans:
B
91.
Predict the product for the following reaction sequence.
Br
CH3CH2CH2CH2Li CH3CCH2CH3
O
Ph3P
ether
OH O
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
92.
Provide the structure for X, Y and Z, for the following reaction sequence.
Br
X
CH3CH2CH2CH2Li
YCH3CCH2CH3
O
+ Ph3P
ether
Z
93.
Provide the structure of the reactants necessary to prepare the following compound
using Wittig reaction.
94.
Predict the product of the following reaction sequence.
O
CH3COOH
O
IV
O
O
O
O
O
OOH
OH
III
II
I
A)
I
B)
II
C)
III
D)
IV
95.
Predict the product of the following reaction sequence.
O
CH3COOH
O
O
O
O
O
O
O
O
O
O
O
I II III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
Ans:
C
96.
Predict the product of the following reaction sequence.
CH3COOH
O
H
O
97.
What is the correct order of migration rate for the following groups in the Baeyer–
Villiger oxidation reaction?
A)
phenyl > methyl > t-butyl > H
B)
phenyl > t-butyl > methyl > H
C)
H > phenyl > methyl > t-butyl
D)
H > phenyl > t-butyl > methyl
E)
methyl > t-butyl > phenyl > H
Ans:
D
98.
Suggest a stepwise synthesis of 1-pentanol from 1-butanal
99.
Suggest a stepwise synthesis of 1-pentanal from 1-butanal.
100.
Suggest a stepwise synthesis of 1-phenylpropanal from benzyl alcohol.
.
101.
Suggest a stepwise synthesis for the following
HO
O
H
OH
102.
Suggest a stepwise synthesis for 4-methyl-1-pentanamine from 3-methyl-1-butanol
103.
Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.
104.
Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane.
105.
Suggest a stepwise synthesis for the following.
O
OH
106.
Suggest a stepwise synthesis for the following.
O
Br
107.
Provide structures of the intermediates and the final product.
OH
PBr3H
O
PCC
Mg/ether
2. H3O+
1.
XYZA
108.
Provide structures of the intermediates and the final product.
Br
O
HOCH2CH2OH H H
O
H2SO4
Mg /ether
1.
2. H2O
H3O+
XY Z A
109.
Provide structures of the intermediates and the final product.
HO
O
OX
TsOH
YH3O+
1. (CH3)2CHLi
2. H2O
Z
110.
Suggest a stepwise synthesis for the following
OH N
111.
Using 1-propanol as your only source of Carbon and using any other reagents as
appropriate write a complete stepwise synthesis for 3-hexanone.
112.
A compound with formula C5H10O shows two singlets, in the 1H NMR spectrum.
Which one of the following is a possible structure for this compound?
A)
CH3CH2CCH2CH3
O
B)
(CH3)2CHCCH3
O
C)
(CH3)3CCH
O
D)
CH3CH2CHCH
CH3
O
E)
(CH3)2CHCH2CH
O
Ans:
C
113.
The 1H NMR spectrum of a compound with formula C7H14O shows two signals. Which
one of the following is a possible structure for this compound?
A)
2-heptanone
B)
3-heptanone
C)
2,4-dimethyl-3-pentanone
D)
2,2-dimethyl-3-pentanone
E)
Two of the above
114.
The 13C NMR spectrum of a compound with formula C7H14O shows five signals. Which
one of the following is a possible structure for this compound?
A)
2-heptanone
B)
3-heptanone
C)
2,2-dimethyl-3-pentanone
D)
2,4-dimethyl-3-pentanone
E)
none of these
Ans:
C
115.
The 1H NMR spectrum of a compound with formula C7H14O shows a doublet at 9.2
ppm. Which one of the following is a possible structure for this compound?
A)
2-methyl-3-hexanone
B)
2-methylhexanal
C)
2,2 -dimethylpentanal
D)
2,2-dimethyl-3-pentanone
E)
None of these
Ans:
B
Ans:
C
116.
Provide a structure for the compound with molecular formula C5H10O and with the
following spectroscopic data.
IR: 1720 cm−1
1H NMR: 1.9 (triplet, I=3H), 1.7 (sextet, I=2H), 2.1 (singlet, I=3H), 2.4 (triplet,
I=2H)
117.
Provide a structure for the compound with molecular formula C9H10O and with the
following spectroscopic data.
IR: 1680 cm−1
1H NMR: 1.25 (triplet, I=3H), 3.0 (quartet, I=2H), 7-8 (multiplet, I=5H)