Chapter Twenty
1.
What is the IUPAC name for the following compound?
O
A)
2-methyl-5-heptanone
B)
7-methyl-4-octanone
C)
6-isopropyl-4-octanone
D)
isobutyl propyl ketone
E)
1,1-dimethyl-4-heptanone
Ans:
B
2.
What is the correct structure for 7-methyl-4-octanone?
O
O
O
O
III III
IV V
O
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
3.
What is the IUPAC name for the following compound?
O
Ans:
5,5-dimethyl-2-heptanone
4.
What is the IUPAC name for the following compound?
A)
2,5-dimethyl-6-hexanal
B)
2,5-dimethylhexanal
C)
1,4-dimethylpentanal
D)
1,4-dimethylhexanal
E)
none of these
Ans:
B
5.
Provide the structure for 4-methylbenzaldehyde.
6.
What is the IUPAC name for the following compound?
O
A)
5,5-dimethyl-2-heptanone
B)
5,5-dimethylcycloheptanone
C)
4,4-dimethylcycloheptanone
D)
3,3-dimethylcycloheptanone
E)
none of these
Ans:
C
7.
What is the IUPAC name for the following compound?
O
A)
2,4-dimethyl-2-pentenone
B)
2,5-dimethylcyclopenten-3-one
C)
2,4-dimethylcyclopent-2-enone
D)
3,5-dimethylcyclopent-2-enone
E)
2-methyl-5-methylcyclopent-2-enone
Ans:
C
8.
Provide the structure for 2,3-dimethyl-2-octen-4-one.
9.
What is the IUPAC name for the following compound?
H
O
A)
4-benzylbutanal
B)
3-phenylpropanal
C)
3-benzylpropanal
D)
4-phenylbutanal
E)
none of these
10.
What is the structure for 5-hydroxy-2-phenyl-3-hexanone?
OH
O
OH
O
OH O
III III
O
OH
IV
H
OH O
V
A)
I
B)
II
C)
III
D)
IV
E)
V
11.
What is the IUPAC name for the following compound?
O
H
Cl
Ans:
4-chloro-3-methylbenzaldehyde
Ans:
C
12.
Provide the structure for m-nitroacetophenone.
13.
What is the IUPAC name for the following compound?
O
Br
A)
(S)-2-methyl-2-bromobutanone
B)
(S)-2-bromo-2-methylcyclobutanone
C)
(R)-2-bromo-2-methylcyclobutanone
D)
(S)-1-bromo-1-methyl-2-cyclobutanone
E)
(R)-1-bromo-1-methyl-2-cyclobutanone
Ans:
B
14.
Provide the structure for (S)-3-chlorocyclohexanone.
15.
What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?
O
Cl
H
O
Cl
III
H
O
Cl
H
Cl O
H
O
Cl
III IV
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
16.
Provide the structure for 7-bromo-1-octyn-4-one.
Br
O
Br
O
Br
OBr
O
III
III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
A
17.
What is the IUPAC name for the following compound?
OH O
A)
4-oxo-5-phenyl-2-hexanol
B)
5-hydroxy-2-phenyl-3-hexanone
C)
2-hydroxy-5-phenyl-4-hexanone
D)
2-hydroxypropyl-1-phenylethyl ketone
E)
5-hydroxy-3-keto-2-phenylhexane
Ans:
B
18.
What is the IUPAC name for the following compound?
O
Ans:
(2S,3R)-2-isopropyl-3-methylcyclohexanone
19.
What is the IUPAC name for the following compound?
O
Br H
A)
(R)-5-bromo-2-heptanal
B)
(S)-5-bromo-2-heptanal
C)
(R)-5-bromo-2-heptanone
D)
(S)-5-bromo-2-heptanone
E)
(R)-2-bromo-6-heptanone
Ans:
C
20.
What is the IUPAC name for the following compound?
O
A)
5-cyclohexyl-2-hexanal
B)
5-cyclohexyl-2-hexanone
C)
5-cyclohexyl-5-methyl-2-pentanone
D)
5-(1-methylcyclohexyl)-2-pentanone
E)
4-(1-methylcyclohexyl)-2-butanone
21.
Provide the structure for benzophenone.
22.
What is the IUPAC name for the following compound?
H H
OO
Ans:
(2R,4R)-2,4-dimethylpentanedial
23.
Predict the product for the following reaction.
PCC
CH2Cl2
2-hexanol
A)
hexanal
B)
hexanoic acid
C)
2-hexanone
D)
2-chlorohexane
E)
1-hexanol
Ans:
C
24.
Predict the product for the following reaction.
OH
N
HCrO3 Cl
CH2Cl2
III III
IV
O
O
H
O
OH
Cl
V
HO
A)
I
B)
II
C)
III
D)
IV
E)
V
25.
Predict the product for the following reaction.
PCC
CH2Cl2
3-methyl-1-octanol
A)
3-methyloctanone
B)
3-methyloctanal
C)
2-methyloctanone
D)
2-methyloctanal
E)
2-methyloctanoic acid
Ans:
B
Ans:
D
26.
Predict the product for the following reaction.
OH
CH2OH PCC , excess
CH2Cl2
O
COH
O
O
CH
O
CH
CH
O
O
OH
COH
O
COH
O
COH
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
27.
Compound A on ozonolysis yields acetophenone and propanal. What is the structure of
compound A?
Compound A 1. O3
2. (CH3)2SAcetophenone + propanal
A)
2-phenyl-2-pentene
B)
1-phenyl-1-hexene
C)
1-phenyl-2-pentene
D)
2-phenyl-2-hexene
Ans:
A
Ans:
B
28.
Compound A on ozonolysis yields the following two products What is the structure of
compound A?
O
H
O
+
2. (CH3)2S
1. O3
Compound A
H
H
H
I II III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
29.
Compound A on ozonolysis yields 2,6-heptanedione. What is the structure of compound A?
Compound A 1. O3
2. (CH3)2S2,6-heptanedione
A)
1,2-dimethylcyclohexene
1.
B)
2,6-dimethylcyclohexene
C)
1,5-dimethylcyclopentene
D)
1,2-dimethylcyclopentene
E)
2-methyl-1-cyclopentene
Ans:
D
Ans:
A
30.
Predict the product for the following reaction.
1.O3
2. (CH3)2S
excess
H
H
O
O
H
H
O
O
H H
OO
OO
O
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
31.
Provide the reagents necessary to carry out the following conversion.
(CH3)2CHCH2C CCH2CH(CH3)23-methylbutanal
Ans:
E
32.
Provide the reagents necessary to carry out the following conversion.
H
O
33.
Predict the product for the following reaction.
H2O / H2SO4
HgSO4
O
OH
HO
C
O
H
OH
HO
III
IV
III
V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
D
34.
Provide the reagents necessary to carry out the following conversion.
O
35.
Provide the reagents necessary to carry out the following conversion.
O
H
A)
1. H2O/ H2SO4, 2. PCC/CH2Cl2
B)
PCC/ CH2Cl2
C)
1. BH3, 2. H2O2/NaOH/H2O
D)
1. O3, 2. Zn/acetic acid
E)
1. BH3, 2. H2O2/NaOH/H2O, 3. PCC
Ans:
C
36.
Provide the reagents necessary to carry out the following conversion.
O
37.
Predict the major product for the following reaction
O
CH3CH2CCl
O
AlCl3
O
O
O
O
O
O
O
Cl
O
I II IV
III
A)
I
B)
II
C)
III
D)
IV
E)
none of these
Ans:
C
38.
Predict the product for the following reaction
AlCl3
O
Cl
Cl
Cl
O
O
III III
O
O
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
C
39.
Predict the product for the following reaction
O
CH3CH2OH
H2SO4
excess
HO OH HO OCH2CH3CH3CH2O OCH2CH3
OCH2CH3
O
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
40.
Predict the product for the following reaction
H
O
CH3OH
H2SO4
excess
OH
OH
H
HO OCH3
H
H3CO OCH3
OCH3
O
OH
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
B
Ans:
C
41.
Provide the structure of the product, when cyclohexanecarbaldehyde reacts with excess
2-propanol in presence of sulfuric acid.
O
OH
O
O
O
OH
O
O
O
O
I
III
II
V
IV
A)
I
B)
II
C)
III
D)
IV
E)
V
Ans:
E
42.
Provide the reagents necessary to carry out the following conversion.
HO O
O
1 mol