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86.
Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine,
followed by sodium bromide.
A)
trans-1-bromo-3-methylcyclopentane
B)
cis-1-bromo-3-methylcyclopentane
C)
1-methylcyclopentene
D)
2-Methylcyclopentene
E)
3-Methylcyclopentene
87.
The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene
goes via_____.
A)
SN1 mechanism
B)
SN2 mechanism
C)
E1 mechanism
D)
E2 mechanism
E)
None of these.
88.
Explain why the following reaction will not produce alcohol as product.
Cl
NaOH
OH
89.
Predict the major product for the following reaction.
OH 1. TsCl/pyridine
2. CH3CH2ONa
90.
Predict the major product for the following reaction.
OH
H2SO4
91.
Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane.
92.
Provide a stepwise curved arrow mechanism for the following reaction.
HO
CH2CH3
CH2CH3H2SO4
CH2CH3
CH2CH3
93.
Predict the product and provide a stepwise curved arrow mechanism for the following
reaction.
H2SO4
heat
OH
OH
94.
Predict the product for the following reaction.
PCC
2-hexanol
CH2Cl2
A)
CH3COH
O
B)
CH3CH2CH2CH2COH
O
C)
CH3(CH2)3CCH3
O
D)
CH3CH2CH2CH2CH2COH
O
E)
CH3CH2CH2CH2CH2CH
O
95.
Provide the reagents necessary to carry out the following conversion.
OH O
A)
KMnO4/NaOH/H2O
B)
CrO3/H2SO4/H2O
C)
H2, Pt
D)
Br2, CCl4
E)
None of these
96.
Predict the product for the following reaction.
OH
Na2Cr2O7/H2SO4/H2O
97.
Predict the product for the following reaction.
OH
CH2Cl2
PCC
98.
Provide the reagents necessary to carry out the following conversion.
OH H
O
A)
KMnO4/NaOH/H2O
B)
CrO3/H2SO4/H2O
C)
PCC/CH2Cl2
D)
Br2, CCl4
E)
None of these
99.
Provide the reagents necessary to carry out the following conversion.
OH OH
O
A)
KMnO4/NaOH/H2O
B)
CrO3/H2SO4/H2O
C)
PCC/CH2Cl2
D)
Br2, CCl4
E)
None of these
100.
Predict the product for the following reaction.
OH
CH2OH
PCC/CH2Cl2
excess
101.
Predict the product for the following reaction.
OH PCC
CH2Cl2
102.
Predict the product for the following reaction.
PCC
CH2Cl2
cis-4-methylcyclohexanol
103.
Provide the structure for the final product (D), in the following reaction sequence.
CH3CH2CHOH
CH3
PBr3A
Mg
B
H3C H
O
C
H2OD
ether
104.
Provide the structure for the final product (E), in the following reaction sequence.
OH PBr3A
Mg
BC
H2O
D
PCC
CH2Cl2
O
O
IV V
ether E
H H
O
OH
OH
III
H
O
III
A)
I
B)
II
C)
III
D)
IV
E)
V
105.
Provide the structure for product (A), in the following reaction sequence.
PBr3
OH
Mg D2OA
ether
A)
CH3CH2CH2CH3
B)
CH3CH2CHDCH3
C)
CH3CH2CHODCH3
D)
CH3CH2CH2CH2OD
E)
CH3CH2CH2CH2D
106.
Provide the reagents necessary to carry out the following conversion.
OH
O
107.
Provide a stepwise synthesis for the following.
108.
Provide the product for the following reaction sequence:
MgBr
H2O
MgBr
H2O
ether
K2Cr2O7/H2SO4/H2O
ether
OH PCC
CH2Cl2
OH OHO
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
109.
Predict the product, for the following reaction sequence,
OH
SOCl2H
O
CrO3/ H2SO4/H2OMg/ether
2. H3O+
1.
pyridine
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
110.
Provide a stepwise synthesis for the following.
O
111.
Provide the reagents necessary to carry out the following conversion.
O
O
112.
Provide the reagents necessary to carry out the following conversion.
HO
O
HO
HO
113.
Provide the reagents necessary to carry out the following conversion.
Br OH
O
114.
Provide a stepwise synthesis to carry out the following conversion.
