Topic: Nomenclature Section: 16.2 Difficulty Level: Hard 21 What is the correct IUPAC name for the following compound?. Answer: B Topic: Physical Properties, Relationships, Stereochemist
Trang 1Package Title: Solomons Test Bank
Course Title: Solomons 11e
Chapter Number: 16
Question type: Multiple Choice
1) What is the correct IUPAC name for the following compound?
Difficulty Level: Easy
2) What is the correct structure for 7-methyl-4-octanone?
Trang 2Section: 16.2
Difficulty Level: Easy
3) What is the correct IUPAC name for the following compound?
Difficulty Level: Easy
4) What is the correct structure for 5,5-dimethyl-2-heptanone?
Trang 35) A correct name for the following compound would be which of those below?
Difficulty Level: Easy
6) What is the correct structure for 2,5-dimethylhexanal?
O
O
H O
H O
Trang 4Difficulty Level: Medium
8) What is the correct IUPAC name for the following compound?
Difficulty Level: Medium
9) What is the correct IUPAC name for the following compound?
Trang 5Difficulty Level: Medium
10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one?
Difficulty Level: Medium
11) A correct name for C6H5CH2CH2CH
O
is?
Trang 6Difficulty Level: Medium
12) What is the correct structure for 3-phenylpropanal?
O H
H O
Difficulty Level: Medium
13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?
Trang 7OH O
OH
Ph
Ph OH
O
Ph
Ph OH
O
Ph
H
O OH
Difficulty Level: Medium
14) Which is the proper name for the structure shown?
Difficulty Level: Medium
15) What is the correct structure for 4-chloro-3-methylbenzaldehyde?
Trang 8H O
H O
H O
H O
Difficulty Level: Medium
16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?
Trang 9H O
H
O
H O
Difficulty Level: Medium
17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?
Trang 10Difficulty Level: Medium
18) What is the correct structure for 7-bromo-1-octyn-4-one?
Trang 11Difficulty Level: Medium
19) What is the correct IUPAC name for the following compound?
O Br
Difficulty Level: Hard
20) What is the correct IUPAC name for the following compound?
Trang 12Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
21) What is the correct IUPAC name for the following compound?
Difficulty Level: Hard
22) What is the correct IUPAC name for the following compound?
Trang 1323) What is the correct IUPAC name for the following compound?
Difficulty Level: Hard
24) What is the correct IUPAC name for the following compound?
Difficulty Level: Hard
25) What is the correct IUPAC name for the following compound?
Trang 14Difficulty Level: Hard
26) What is the IUPAC name for
CH 3 CH OH
CH 2 C CH O
C 6 H 5
CH 3
? a) 4-Oxo-5-phenyl-2-hexanol
Difficulty Level: Hard
27) Which is the proper name for the structure shown?
Trang 15Section: 16.2
Difficulty Level: Hard
28) Which is the proper name for the structure shown?
O Cl
Difficulty Level: Hard
29) Which is the proper name for the structure shown below?
Difficulty Level: Hard
30) What is the correct structure for (R)-7-bromo-1-octyn-4-one?
Trang 16O
O Br
Br
O
O Br
Difficulty Level: Hard
31) What is the correct structure for (S)-7-bromo-1-octyn-4-one?
Br
O
O Br
Br
O
O Br
Trang 17Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
32) Which is the IUPAC name for the structure shown below?
Difficulty Level: Hard
33) Which is the IUPAC name for the structure shown below?
Difficulty Level: Hard
34) What is the correct structure for (R)-5-bromo-2-heptanone?
Trang 18Br H
Difficulty Level: Hard
35) What is the correct structure for (S)-5-bromo-2-heptanone?
Br
Br H
V
Trang 19Difficulty Level: Hard
36) Which is the IUPAC name for the structure shown below?
Oa) 5-Cyclohexyl-2-hexanal
Difficulty Level: Hard
37) What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?
Trang 20e) V
Answer: D
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
38) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?
Difficulty Level: Hard
39) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?
Trang 21Difficulty Level: Hard
40) Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight.)
Difficulty Level: Easy
41) Stereoisomers can exist in the case of which of the following?
a) The hydrazone of butanone
b) The oxime of acetone
c) The phenylhydrazone of cyclohexanone
d) The cyclic acetal formed from propanal and ethane-1,2-diol
e) The imine of cyclopentanone
Answer: A
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.8
Difficulty Level: Medium
42) Stereoisomers can exist in the case of which of the following?
a) The hydrazoneof benzophenone
b) The oxime of 2-methylcyclopentanone
Trang 22c) The phenylhydrazone of 4-methylcyclohexanone
d) The imine of cyclopentanone
e) Two of these choices
Answer: B
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.8
Difficulty Level: Medium
43) In which of the following reactions is the final product expected to be formed as a racemic mixture?
Difficulty Level: Medium
44)Acetals are unstable in the presence of an aqueous solution of which of these?
a) HCl
b) NaOH
c) KHCO3
Trang 23Answer: A
Topic: Reagents
Section: 16.7
Difficulty Level: Easy
45) LiAlH4 (LAH) cannot be used to convert carboxylic acids to the corresponding aldehydes because:
a) LAH is not sufficiently reactive
b) RCOOH is converted into RCOOLi
c) RCOOH is reduced to RCH2OH
Difficulty Level: Easy
46) Identify the reagent(s) that would bring about the following reaction:
Difficulty Level: Easy
47) Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group
of an aldehyde or ketone?
a) I
-b) H O+
Trang 24Difficulty Level: Easy
48) Which reagent(s) could be used to carry out the following transformation?
d) All of these choices
e) Two of these choices
Answer: E
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
49) The following reduction can be carried out with which reagent(s)?
d) None of these choices
e) All of these choices
Answer:E
Trang 25Difficulty Level: Medium
50) The following reduction can be carried out with which reagent(s)?
Difficulty Level: Medium
51) Which reagent will not differentiate between 3-butenal and 2-butanone?
is produced by the reaction of an excess of benzaldehyde with which compound?
a) Ammonia
b) Hydrazine
c) Nitrogen
d) Phenylhydrazine
Trang 26Answer: B
Topic: Reagents
Section: 16.8
Difficulty Level: Medium
53) The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the Baeyer-Villiger oxidation is:
a) H >Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl
b) Ph- > H>3° alkyl>2° alkyl>1° alkyl>methyl
c) 3° alkyl > 2° alkyl > 1° alkyl > methyl>H >Ph-
d) 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph->H
e) H > 3° alkyl > 2° alkyl > 1° alkyl > methyl>Ph-
Answer:A
Topic: Mechanisms
Section: 16.12
Difficulty Level: Medium
54) Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound?
Trang 27Difficulty Level: Medium
56) Select the structure of the major product in the following reaction
Trang 28Answer:D
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
57) Select the structure of the major product in the following reaction
Difficulty Level: Medium
58) Select the structure of the major product in the following reaction
Trang 29Difficulty Level: Medium
59) Select the structure of the major product in the following reaction
Trang 30Difficulty Level: Medium
60) Select the structure of the major product in the following reaction
Trang 31Difficulty Level: Medium
61) Select the structure of the major product in the following reaction
Trang 32Difficulty Level: Medium
62) Select the structure of the major product in the following reaction
Trang 33Difficulty Level: Medium
63) Select the structure of the major product in the following reaction
?
Trang 34Difficulty Level: Medium
64) What is the final product, Z, of the following synthesis?
Trang 35Answer: C
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium
65) Select the structure of the major product in the following reaction
Difficulty Level: Medium
66) Select the structure of the major product in the following reaction
?
H2SO4HgSO4, H2O
Trang 36Difficulty Level: Medium
67) Select the structure of the major product in the following reaction
i.) KMnO4, OH - , hot
Difficulty Level: Medium
68) Select the structure of the major product in the following reaction
i.) KMnO4, OH-, hot
ii) H3O+
?
Trang 37Difficulty Level: Medium
69) What would be the product of the following reaction sequence?
IV
VIII
H
O O
OH
O OH
Trang 3870) The product, K, of the following sequence of reactions
Difficulty Level: Medium
71) The product, K, of the following sequence of reactions would be:
Trang 39Difficulty Level: Medium
72)The product, J, of the following sequence of reactions would be:
Trang 40Difficulty Level: Medium
73) The product, E, of the following sequence of reactions
would be:
Trang 41O OH
Cl O
Difficulty Level: Medium
74) The product, E, of the following sequence of reactions
would be:
Trang 42Difficulty Level: Medium
75) The product, E, of the following sequence of reactions
would be:
Trang 43Cl O
Difficulty Level: Medium
76) The product, C, of the following reaction sequence,
Trang 44Section: 16.9
Difficulty Level: Medium
77) The product, D, of the following reaction sequence,
Difficulty Level: Medium
78) What is the major product of the following reaction sequence?
Trang 45Difficulty Level: Medium
79) What is the major product of the following reaction sequence?
Trang 46Difficulty Level: Medium
80) What is the major product of the following reaction sequence?
H2Oheat
a) I
b) II
c) III
Trang 47Answer: B
Topic: Reaction Products
Section: 16.9
Difficulty Level: Medium
81) The product, H, of the following reaction sequence,
Difficulty Level: Medium
82) What would be the final product?
C6H5CCH3O
Trang 48Difficulty Level: Medium
83) What would be the final product?
Trang 49Topic: Reaction Products
Section: 16.10
Difficulty Level: Medium
84) What is the reactant W in the synthesis given below?
O
Ph3P + W
C6H5Li
Wittig reagent
Difficulty Level: Medium
85) Predict the major organic product of the following reaction:
O H
H3C
OH
O H
O H
Ag(NH3)2
a) I
Trang 50Difficulty Level: Medium
86) The product, H, of the following reaction sequence,
Difficulty Level: Hard
87) What would be the product of the following reaction sequence?
Trang 51OH O
Difficulty Level: Hard
88) What would be the product of the following reaction sequence?
OH O
i) PCl3ii) C6H6, AlCl3iii) HSCH2CH2SH, BF3iv) Raney Ni (H2)
?
OH
Trang 52Difficulty Level: Hard
89) What would be the product of the following reaction sequence?
Difficulty Level: Hard
90) What would be the product of the following reaction sequence?
Trang 53Difficulty Level: Hard
91) What would be the product of the following reaction sequence?
IV
OH O
?
Trang 54Difficulty Level: Hard
92) What would be the product of the following reaction sequence?
Difficulty Level: Hard
93) What would be the product of the following reaction sequence?
Trang 55OH O
Difficulty Level: Hard
94) What would be the product of the following reaction sequence?
Trang 56Difficulty Level: Hard
95) What would be the product of the following reaction sequence?
Difficulty Level: Hard
96) What would be the product of the following reaction sequence?
Trang 57OH O
Difficulty Level: Hard
97) What would be the product of the following reaction sequence?
OH O
OH
i) PCl3ii) C6H6, AlCl3iii) Zn(Hg), HCl, heat
?
OH
Trang 58Difficulty Level: Hard
98) What would be the product of the following reaction sequence?
Trang 5999) The product, E, of the following reaction sequence,
Difficulty Level: Hard
100) The product, D, of the following sequence of reactions
Trang 60Difficulty Level: Hard
101) The product, D, of the following sequence of reactions
Difficulty Level: Hard
102)The product, D, of the following sequence of reactions
Trang 61Difficulty Level: Hard
103) The product, E, of the following reaction sequence,
CH2CH2CH3 COCH2CH3
O
CCH2CH3
O CHCH2CH3
Trang 62e) V
Answer: C
Topic: Reaction Products
Section: 16.5
Difficulty Level: Hard
104) What is the final product of this synthetic sequence?
FeCl3
Mgether
Difficulty Level: Hard
105) Select the structure of the major product in the following reaction
?
i) H2, Lindlar catalystii) O3
Trang 63Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
106) Select the structure of the major product in the following reaction
?
i) H2, P-2ii) O3iii)Zn, CH3CO2H
Difficulty Level: Hard
107) Select the structure of the major product in the following reaction
?
i) H2, Ni2Bii) O3iii)Zn, CH3CO2H
Difficulty Level: Hard
108) Select the structure of the major product in the following reaction
Trang 64i) Li, NH3(l)ii) O3iii)Zn, CH3CO2H
Difficulty Level: Hard
109) What new compound will eventually be formed when HCl is added to a solution of pentanal
Difficulty Level: Hard
110) What is the major product of the following reaction sequence?
Trang 65HCN H2SO4
H2O heat
Difficulty Level: Hard
111) What is the major product of the following reaction sequence?
OH
Trang 66Difficulty Level: Hard
112) Select the structure of the major product in the following reaction
?
i) H2, Lindlar catalystii) O3
Difficulty Level: Hard
113) Which of the following reactions would yield benzaldehyde?
Trang 67a)
C6H5CH2Cl OH
-H2Oheatb) C6H5CH(OCH3)2 H3O
+
c)
2 H2O
d) Two of these choices
e) All of these choices
Answer: B
Topic: Synthesis
Section: 16.7
Difficulty Level: Easy
114) Which of the following procedures would not yield 3-pentanone as a major product?
Trang 68H O
Trang 69H O
would be:
H
H2O, H2SO4HgSO4
Trang 70H O
would be:
H
H2O, H2SO4HgSO4
Trang 71H O
PCC
CH2Cl2OH
Trang 72H O
1 DMSO, (COCl)2
2 Et3N OH
Trang 73H O
Difficulty Level: Medium
121) Which synthesis or syntheses would yield propanal?
a)
CH2Cl2
Trang 74b)
CH3CH2CCl
O
LiAlH[OC(CH3)3]3ether, -78 oC
c)
CH3C CH
1 Sia2BH
2 H2O2, OHd) All of these choices
-e) None of these choices
Answer: D
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
122) Which synthesis or syntheses would yield propanal?
c)
CH3C CH
1 Sia2BH
2 H2O2, OHd) All of these choices
-e) None of these choices
Answer: D
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
123) Which synthesis or syntheses would yield propanal?
a)
CH2Cl2
Trang 75b)
CH3CH2CCl
O
LiAlH[OC(CH3)3]3ether, -78 oC
c)
d) All of these choices
e) None of these choices
Answer: D
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
124) Which synthesis or syntheses would yield propanal?
d) All of these choices
e) None of these choices
Answer: D
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
125) Which synthesis or syntheses would yield propanal?
a)
Trang 76b)
c)
d) All of these choices
e) None of these choices
Answer: D
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
126) Which of the reactions listed below would serve as a synthesis of acetophenone,
d) Two of these choices
e) All of these choices
Answer: E
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
127) Which of the reactions listed below would serve as a synthesis of acetophenone,
O
Trang 77b) C6H6 + CH3COCl AlCl3
+
d) Two of these choices
e) All of these choices
Answer: E
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
128) Which of the following would yield 3-pentanone as the major product?
d) Two of these choices
e) All of these choices
Answer: E
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
129) Which sequence of reactions would be utilized to convert