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Chapter Twenty Two
1.
Which one of the following compounds is most acidic?
A)
ethyl acetoacetate
B)
2-butanone
C)
ethyl pentanoate
D)
1-butanol
E)
3-pentanone
2.
Which are the most acidic - hydrogens in the following compounds?
III
I II IV V
CH3CH2CCH2CCH2CH3
O O
CH3CH2CCH2COCH2CH3
O O
CH3CH2COCH2CH3
O
CH3CH2CH
O
CH3CH2CCH2CH3
O
A)
I
B)
II
C)
III
D)
IV
E)
V
3.
Which is the most acidic hydrogen in the following compound?
II
I
O
CN
H
H
H
H
H
H H
III
V
IV
A)
I
B)
II
C)
III
D)
IV
E)
V
4.
Which is the most acidic hydrogen in the following compound?
I
O
O O
O
HO
H
H
H
H
H H
II
III
IV
A)
I
B)
II
C)
III
D)
IV
E)
all of these
5.
Which one of the following is the most acidic compound?
O
O
O O
O
O
O
O
O
I II III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
6.
Which of the following is(are) a keto-enol tautomeric pair(s)?
CH3CH CH
O
CH3CH CH
O
I
CH3CCH2
OH
II
CH3CCH3
O
CH3CCH2
O
CH3CCH2
O
III
A)
I
B)
II
C)
III
D)
I & II
E)
I & III
7.
Which of the following is (are) a keto-enol tautomeric pair(s)?
O
I
OH
O
IV
O
OH
II
OH
O
V
O
III
OH
O
A)
I
B)
II
C)
III
D)
IV
E)
V
8.
Which one of the following compounds would favor the enol tautomer over the ketone
tautomer?
O O O
O
O
H
O
O
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
9.
Explain why the following equilibrium favors the enol tautomer.
OOOOH
10.
Explain why the following equilibrium favors the enol tautomer.
OOH
11.
Provide the structure of the enol when 3,3,6-trimethyl-4-heptanone is treated with acid.
12.
Provide the structure of the enolate when acetophenone is treated with strong base.
13.
Which of the following base will completely convert 1,4-cyclohexanedione into an
enolate?
A)
sodium hydroxide
B)
sodium ethoxide
C)
LDA
D)
sodium hydride
E)
both C & D
14.
Which one of the following compounds would undergo racemization at the
-stereocenter in presence of a base?
OO
H
O O
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
15.
Which of the following compound(s) would undergo racemization in presence of a
base?
H
O
H
O
H
O
CH3
O
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
II & III
16.
Predict the major product for the following reaction.
O
H3O+
Cl2
O
Cl
O
Cl
O
Cl
O
Cl
Cl
III III IV
O
Cl
Cl
V
A)
I
B)
II
C)
III
D)
IV
E)
V
17.
Predict the major product for the following reaction.
OH PCC H3O+
Br2
CH2Cl2
H
O
H
BrHO
H
O
Br
H
O
Br
III III
IV
Br
O
V
A)
I
B)
II
C)
III
D)
IV
E)
V
18.
Provide The reagents necessary to carry out the following conversion.
OH H
O
19.
Provide The reagents necessary to carry out the following conversion.
OH O
CN
20.
Predict the major product for the following reaction.
O
H3O+
Br2
pyridine
OO
Br
OH
O
III
III IV
O
+
O
+
A)
I
B)
II
C)
III
D)
IV
E)
none of these
21.
Predict the major product for the following reaction and provide a curved arrow
mechanism for the formation of the product.
O
H3O+
Br2
22.
Predict the major product for the following reaction.
OH
O
1. Br2/PBr3
2. H2O
Br
O
OH
O
Br
Br
O
Br
OH
HO Br
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
23.
Predict the major product for the following reaction.
OH K2Cr2O7/H2SO4/H2O1. Br2/PBr3
2. H2O
H
O
Br
Br
Br
OH
O
Br
Br
O
Br
III III IV
Br
O
V
A)
I
B)
II
C)
III
D)
IV
E)
V
24.
Provide the reagents necessary to carry out the following conversion.
CN
OH
O
Br
25.
Which of the following ketones will give a positive iodoform test?
A)
3-heptanone
B)
3-hexanone
C)
cyclohexanone
D)
2-pentanone
E)
2-methyl-3-hexanone
26
Predict the major product for the following reaction.
O
1. NaOH/Br2
2. H3O+
O
Br
O
Br
Br Br
HO
OH
OH
O
BrO
OH
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
27.
Provide the reagents necessary to convert acetophenone to benzoic acid.
A)
K2Cr2O7/H2SO4/H2O
B)
1. NaOH/Br2 2. H3O+
C)
1. KMnO4/NaOH/H2O
D)
1. Br2/PBr3 2. H2O
E)
both A & C
28.
Predict the major product for the following reaction.
1. NaOH/I2
2. H3O+
O
III III
IV V
O
I
HO
OO
I
II
I
O
HO
OH
A)
I
B)
II
C)
III
D)
IV
E)
V
29.
Predict the major product for the following reaction sequence.
OH
2. H3O+H2SO4
CH3OHKMnO4/NaOH/H2O 1. NaOH/I2
30.
Provide the reagents necessary to carry out the following conversion.
O
N
H
O
Br
31.
Provide the reactant that would yield m-chlorobenzoic acid using the haloform reaction.
CCH3
Cl
O
CCH2CH3
Cl
O
COH
O
CH
Cl
O
CH2Cl
Cl
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
32.
Which one of the following compound does not undergo an aldol addition reaction in
presence of aqueous sodium hydroxide?
A)
butanal
B)
2-methylbutanal
C)
3-methylpentanal
D)
2,2-dimethylbutanal
E)
none of these
33.
Predict the major product for the following reaction.
H
O
NaOH/H2O
H
OOH
H
OO
OH
OH
H
OO
OH
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
34.
Predict the major product for the following reaction.
butanal + 2,2-dimethylpentanal NaOH, H2O
OH
H
O
H
OOH
OH
O
OH
H
OOH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
35.
Predict the major product for the following reaction.
H
O
H
O
+
NaOH/H2O
H
OO
H
OHOH
H
OO
H
OOH
OH
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
36.
Predict the product when cyclohexanone reacts with aqueous sodium hydroxide at
1000C.
O
O
O
O
III III
O
IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
37.
Predict the product for the following reaction.
H
O
NaOH/H2O
H
O
H
O
III
H
OO O
III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
38.
Predict the product for the following reaction.
H
O
O
O
O
NaOH/H2O
+
O
O
O
O
O
O
O
O
OO
O
O
O
III
III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
