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55.
Predict the product for the following reaction.
COCH3
O
1. LiAlH4
2. H2O
excess
56.
Predict the product for the following reaction.
HgSO4
H2O / H2SO4NaBH4/CH3OH
57.
Provide the reactant (A) for the following reaction
1. LiAlH4
2. H2O
5-methyl-3-heptanol
A
O
H
O
H
OO
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
58.
Provide the reagents necessary to carry out the following conversion.
cyclohexene cis-1,2-cyclohexanediol
A)
KMnO4, NaOH
B)
KMnO4, H3O+, 75oC
C)
H2SO4, heat
D)
1. mCPBA 2. H3O+
E)
none of these
59.
Predict the product(s) for the following reaction sequence.
3-hexyne H2/Ni2B1. OsO4
2. NaHSO3
HO
HOH
HHO
HO H
HH
HO OH
H
III III
A)
I
B)
II
C)
III
D)
Both I & II
E)
None of these
60.
Provide the reagents necessary to carry out the following conversion.
cyclohexene trans-1,2-cyclohexanediol
A)
KMnO4, NaOH
B)
KMnO4, H3O+, 75oC
C)
H2SO4, heat
D)
1. mCPBA 2. H3O+
E)
none of these
61.
Provide the structure(s) of the product(s) in the following reaction sequence.
A
CH3CH2ONa
B
Br2
h
mCPBA NaOH/H2O
CD
62.
Predict the product for the following reaction.
NaBH4/CH3OH
O
H
O
excess
OH
H
OO
OH
OH
OH
OH
OH
OH
III III
IV
OH
OH
V
A)
I
B)
II
C)
III
D)
IV
E)
V
63.
Predict the product(s) for the following reaction.
O
H3O+
OH OH
OH
OH
OH
O
H
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
64.
Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
65.
Provide the reagent(s) necessary to carry out the following conversion.
OH
OH
66.
Predict the product(s) for the following reaction.
O
O
2. H2O
1. excess LiAlH4
O
67.
Predict the product for the following reaction sequence.
O
2. H2O
1. CH3CH2MgBr
68.
Predict the product for the following reaction sequence.
Br
H
O
Mg/ether
2. H2O
1.
69.
Provide the reagent(s) necessary to carry out the following conversion.
COCH3
O
OH
70.
Predict the product for the following reaction.
1. CH3CH2CH2MgBr/ether
2. H2O
O
OH
HO
I II
OH
IV
III
OH
A)
I
B)
II
C)
III
D)
IV
E)
None of these
71.
Predict the product for the following reaction.
Br
Mg/ether H H
O
1.
2. H2O
72.
Provide the reagent(s) necessary to carry out the following conversion.
HO
73.
Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard
reaction.
74.
Predict the product for the following reaction.
OCH3
O
2. H2O
1. CH3CH2CH2MgBr
excess
75.
Provide the reagent(s) necessary to carry out the following conversion.
HO Br HO
OH
76.
Predict the product(s) for the following reaction sequence.
Br
OH
AB
O
CTBAF D
(CH3)3SiCl
(CH3CH2)3N
Mg/ ether
1.
2. H2O
77.
Predict the product(s) for the following reaction sequence.
Br
OH
H H
O
TBAF (CH3)3SiCl
(CH3CH2)3N
Mg/ ether
1.
2. H2O
A)
2,4-heptanediol
B)
1,4-heptanediol
C)
2,5-octanediol
D)
1,5-octanediol
E)
none of these
78.
Provide the reagents necessary to carry out the following conversion.
HO HO
79.
Which of the following could be used to synthesize 1-bromopentane?
A)
CH3CH2CH2CH=CH2 + HBr ⎯⎯⎯⎯→
B)
CH3CH2CH2CH2CH2OH + PBr3 ⎯⎯⎯⎯→
C)
CH3CH2CH2CH2CH2OH + NaBr ⎯⎯⎯⎯→
D)
CH3CH2CH2CH2CH2OH + Br2 ⎯⎯⎯⎯→
E)
CH3CH2CH2CH=CH2 + Br2 ⎯⎯⎯⎯→
80.
Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3-
methylbutane.
A)
conc. HBr
B)
Br2
C)
NaBr, H2SO4
D)
PBr3
E)
HBr, peroxide
81.
Predict the product for the following reaction.
OH
PBr3
82.
Predict the major product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
OH
HBr
83.
Predict the major product for the following reaction.
OH
HCl
84.
Predict the product for the following reaction.
SOCl2/pyridine
OH
85.
Predict the major product for the following reaction.
H
H
OH
CH3
1. TsCl /pyridine
2. NaI
H
H
I
CH3
H
H
OTsI
CH3
I
H
H
CH3
H
H
Ts
CH3
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
both I and III
