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.
Ans:
C
88.
Explain why the following reaction will not produce alcohol as product.
Cl
NaOH
OH
nucleophile. Instead, the hydroxide ion is a strong base and will react with the
alkyl chloride to form alkene via an E2 mechanism.
Ans:
A
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
Ans:
B
Ans:
C
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
Ans:
C
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
Ans:
B
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
Ans:
B
Ans:
C
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
Ans:
B
Ans:
C
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.