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49.
Predict the product for the following reaction.
OH
O
SOCl2
pyridine
Cl
O
SO2Cl
O
OCl
O
OH
O
Cl
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
50.
Predict the product for the following reaction.
Cl
O
CH3CH2OH
pyridine
A)
ethyl-3-methylbutanoate
B)
ethyl-2-methylpropanoate
C)
isobutylethanoate
D)
5-methyl-3-hexanone
E)
none of these
51.
Predict the product for the following reaction.
SOCl2(CH3)2CHCH2OH A
1. KMnO4/NaOH/H2O
2. H3O+pyridine pyridine
O
O
O
O
Cl
O
Cl
III
IV
O
III
A)
I
B)
II
C)
III
D)
IV
E)
none of these
52.
Predict the product for the following reaction.
Cl
O
pyridine
OH
53.
Predict the product for the following reaction.
OH
O
1. SOCl2/pyridine
2. LiAl[OC(CH3)3]H
H
O
Cl
O
OCH3
OH
O
SOCl
OH
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
54.
Provide the reagents necessary to carry out the following conversion.
4-ethylheptanoyl chloride 5-ethyl-2-octanone
A)
CH3Li
B)
CH3MgBr
C)
(CH3)2CuLi
D)
1. Mg/ether 2. CH3Br
E)
none of these
55.
Provide the reagents necessary to carry out the following conversion.
5-phenyl-1-pentanol
A
5-phenylpentanoic acid
B5-phenylpentanoyl chloride
C
8-phenyl-4-octanone
56.
Provide the reagents necessary to carry out the following conversion.
CH2CH3
OH
CH2CH3
57.
Provide a stepwise synthesis for the following compound using benzyl alcohol as your
only source of carbon and using any other reagents necessary.
OH
C
H2
CH2
58.
Predict the product for the following reaction.
OH
O
1. PCl3
2. CH3CH2NH2
2 mol
59.
Provide the reagents necessary to convert 4,5-dimethyl-1-hexanol into N-cyclopentyl-
4,5-dimethylhexaneamide
60.
Predict the product for the following reaction.
COH COH
OO
61.
Predict the product for the following reaction.
Cl
O
ONa
O
O
O O O O
Cl
O
O
O
O
III
IV
III
A)
I
B)
II
C)
III
D)
IV
E)
none of these
62.
Predict the product for the following reaction.
ONa
O
Cl
O
+
63.
Which of the following reactions would not yield isopropyl acetate as major product?
A)
(CH3C)2O
O
+ (CH3)2CHOH
B)
(CH3C)2O
O
+ CH3CH2CH2OH
C)
CH3CCl
O
+ (CH3)2CHOH pyridine
D)
CH3COH
O
H2SO4
+ (CH3)2CHOH
E)
A & C
64.
Predict the product for the following reaction.
OH O
O
O
+
65.
Predict the product for the following reaction.
O
O
O
1. CH3CH2OH
2. H3O+
HO OH
O O
HO O
O O
O O
O O
O
O
O
OH
O
O
OH
HO O
III
III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
66.
Predict the product for the following reaction sequence.
OO
O
H3O+SOCl2CH3CH2OH
AlCl3
pyridine
67.
Predict the product for the following reaction.
O
O
O
CH3CH2NH2
NHCH2CH3
O
OH
O
NCH2CH3
O
O
III
V
OH
O
OH
O
IV
O
O
NCH2CH3
I
O
O
HO
NHCH2CH3
II
A)
I
B)
II
C)
III
D)
IV
E)
V
68.
Predict the product for the following reaction.
H2O
excess
O
O
O
69.
Provide the reagents necessary to carry out the following conversion.
O
O O
HO
OO
+
70.
Provide the reagents necessary to carry out the following reaction sequence.
OH OH
O
O
O
O
AB
COH
71.
Predict the product for the following reaction.
OH
O
OH
H2SO4
+
O
O
O
O
O
O
OH
O
O
III
III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
72.
Predict the product for the following reaction.
H3O+
OH
OH
O
73.
Predict the product for the following reaction and provide a stepwise curved arrow
mechanism for the formation of the product.
O
O
CH3OH
H2SO4
74.
Which of the following reactions would not yield propyl butanoate as major product?
A)
OH
O
OH H2SO4
+
B)
Cl
O
OH
+
pyridine
C)
O
O O
OH
+
D)
NH2
O
OH H2SO4
+
E)
all of these
75.
Predict the product(s) for the following reaction.
O
O
O
O
NH3
excess
76.
Predict the product(s) for the following reaction.
OO
O
OCH2CH3KOH
excess
77.
Provide the reagents necessary to carry out the following conversion.
O
O
OH
A)
NaBH4/CH3OH
B)
Na/NH3
C)
1. LiAlH4 2. H2O
D)
H3O+/heat
E)
A & C
