Ch.16 Aldehydes, Ketones, Carbonyl Test Questions & Answers - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
Package Title: Solomons Test Bank
Course Title: Solomons 12e
Chapter Number: 16
Question type: Multiple Choice
1) What is the correct IUPAC name for the following compound?
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
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
2) What is the correct structure for 7-methyl-4-octanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
3) What is the correct IUPAC name for the following compound?
a) 5,5-Dimethyl-2-heptanone
b) 5-Ethyl-5,5-dimethyl-methyl-2-octanone
c) 5-Ethyl-5-methyl-2-hexanone
d) 5,5-Dimethyl-2-octanone
e) 3,3-Dimethyl-6-heptanone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
4) What is the correct structure for 5,5-dimethyl-2-heptanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
5) A correct name for the following compound would be which of those below?
a) 2,5-Dimethyl-6-hexanal
b) 2,5-Dimethylhexanal
c) 2-Aldehydoisohexane
d) 3,5-Dimethylheptanone
e) 1-Hydro-2,5-dimethyl-1-hexanone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
6) What is the correct structure for 2,5-dimethylhexanal?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Easy
7) What is the correct IUPAC name for the following compound?
a) 5,5-Dimethyl-2-heptanone
b) 5-Ethyl-5,5-dimethyl-methyl-2-octanone
c) 5,5-Dimethylcycloheptanone
d) 4,4-Dimethylcycloheptanone
e) 3,3-Dimethylcycloheptanone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
8) What is the correct IUPAC name for the following compound?
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
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
9) What is the correct IUPAC name for the following compound?
a) 1,1,2-Trimethyl-1,3-hexenone
b) 1,2-Dimethyl-1,3-hexenone
c) 2,3-Dimethyl-1,3-heptenone
d) 2,3-Dimethyl-2-hepten-4-one
e) 5,6-Dimethyl-5-hepten-4-one
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
10) What is the correct structure for 2,3-dimethyl-2-hepten-4-one?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
11) A correct name for 
is?
a) 3-Benzylpropanone
b) 3-Phenylpropanal
c) 3-Benzylpropanal
d) Nonanone
e) Nonanal
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
12) What is the correct structure for 3-phenylpropanal?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
13) What is the correct structure for 5-hydroxy-2-phenyl-3-hexanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
14) Which is the proper name for the structure shown?
a) 2-Chloro-5-aldehydotoluene
b) 6-Chloro-3-aldehydotoluene
c) 2-Methyl-4-aldehydochlorobenzene
d) 4-Chloro-3-methylbenzaldehyde
e) 4-Methyl-5-chloro-2-benzaldehyde
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
15) What is the correct structure for 4-chloro-3-methylbenzaldehyde?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
16) What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
17) What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
18) What is the correct structure for 7-bromo-1-octyn-4-one?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Medium
19) What is the correct IUPAC name for the following compound?
a) 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
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
20) What is the correct IUPAC name for the following compound?
a) 2-Bromobutanone
b) (S)-2-Bromo-cyclobutanone
c) (R)-2-Bromo-cyclobutanone
d) (S)-1-Bromo-2-cyclobutanone
e) (R)-1-Bromo-2-cyclobutanone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
21) What is the correct IUPAC name for the following compound?
a) (S)-3-chloro-1-hexanone
b) (S)-1-chloro-3-hexanone
c) (R)-3-chlorocyclohexanone
d) (S)-3-chlorocyclohexanone
e) (S)-1-chloro-3-cyclohexanone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
22) What is the correct IUPAC name for the following compound?
a) (S)-3-chloro-1-hexanone
b) (S)-1-chloro-3-hexanone
c) (R)-3-chlorocyclohexanone
d) (S)-3-chlorocyclohexanone
e) (S)-1-chloro-3-cyclohexanone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
23) What is the correct IUPAC name for the following compound?
a) (1S,4R)-bicyclo[2.2.1]hexan-2-one
b) (1S,4R)-bicyclo[2.1.2]heptan-2-one
c) (1S,4R)-bicyclo[2.2.1]heptan-2-one
d) (1R,4S)-bicyclo[2.1.1]heptan-2-one
e) (1S,4S)-bicyclo[2.1.2]heptan-2-one
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
24) What is the correct IUPAC name for the following compound?
a) bicyclo[1.1.0]butan-2-one
b) bicyclo[1.0.1]butan-2-one
c) bicyclo[1.1.0]pentan-2-one
d) bicyclo[0.1.1]butan-2-one
e) bicyclo[1.0.1]pentan-2-one
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
25) What is the correct IUPAC name for the following compound?
a) bicyclo[1.1.1]pentan-2-one
b) bicyclo[1.1.0]pentan-2-one
c) cyclopentanone
d) methylenepentan-2-one
e) bicyclo[1.0.1]pentan-2-one
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
26) What is the IUPAC name for 
?
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
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
27) Which is the proper name for the structure shown?
a) 3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal
b) 3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
c) 3-Methyl-5-(2,5-dinitrophenyl)pentanal
d) 3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde
e) 3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
28) Which is the proper name for the structure shown?
a) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
b) 3-Methyl-5-(4-chlorophenyl)hexanol
c) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
d) 3-Methyl-5-(4-chlorophenyl)hexanaldehyde
e) 3-Methyl-5-(4-chlorophenyl)hexanal
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
29) Which is the proper name for the structure shown below?
a) 7-Bromo-1,4-octynal
b) 7-Bromo-1,4-octynone
c) 2-Bromo-5,7-octynal
d) 7-Bromo-7-methyl-1-heptyne-3-ketone
e) 7-Bromo-1-octyn-4-one
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
30) What is the correct structure for (R)-7-bromo-1-octyn-4-one?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
31) What is the correct structure for (S)-7-bromo-1-octyn-4-one?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
32) Which is the IUPAC name for the structure shown below?
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)-3-Bromopentyl methyl ketone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
33) Which is the IUPAC name for the structure shown below?
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)-3-Bromopentyl methyl ketone
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
34) What is the correct structure for (R)-5-bromo-2-heptanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
35) What is the correct structure for (S)-5-bromo-2-heptanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
36) Which is the IUPAC name for the structure shown below?
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
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
37) What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
38) What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty Level: Hard
39) What is the correct structure for (R)-4-cyclohexyl-3-methyl-2-butanone?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature
Section: 16.2
Difficulty 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.)
a) Pentane
b) 1-Butanol
c) Butanal
d) 1-Fluorobutane
e) Diethyl ether
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.3
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
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 hydrazone of benzophenone
b) The oxime of 2-methylcyclopentanone
c) The phenylhydrazone of 4-methylcyclohexanone
d) The imine of cyclopentanone
e) Two of these choices.
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?
a)
b)
c)
d)
e)
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.9
Difficulty Level: Medium
44) Acetals are unstable in the presence of an aqueous solution of which of these?
a) HCl
b) NaOH
c) KHCO3
d) Na2CO3
e) NaCl
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.
d) RCOOH is reduced to RCH3.
e) RCOOH is converted into R2C=O.
Topic: Reagents
Section: 16.4
Difficulty Level: Easy
46) Identify the reagent(s) that would bring about the following reaction:
CH3CH2CH2COCl CH3CH2CH2CHO
a) H2/Ni
b) Li/liq. NH3
c) LiAlH[OC(CH3)3]3, ether
d) NaBH4, CH3OH
e) LiAlH4, ether
Topic: Reagents
Section: 16.4
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) H3O+
c) AlCl3
d) BF3
e) ZnCl2
Topic: Reagents
Section: 16.6
Difficulty Level: Easy
48) Which reagent(s) could be used to carry out the following transformation?
a) Zn(Hg), HCl, reflux
b) LiAlH4, ether
c) HSCH2CH2SH, BF3; then Raney Ni (H2)
d) All of these choices.
e) Two of these choices.
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
49) The following reduction can be carried out with which reagent(s)?
a) Zn(Hg), HCl
b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
c) H2NNH2, KOH
d) None of these choices.
e) All of these choices.
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
50) The following reduction can be carried out with which reagent(s)?
a) Zn(Hg), HCl
b) i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
c) NaBH4, CH3OH
d) Zn(Hg), HCl and i) HSCH2CH2SH, BF3 ; ii)Raney Ni (H2)
e) Zn(Hg), HCl and NaBH4, CH3OH
Topic: Reagents
Section: 16.7
Difficulty Level: Medium
51) Which reagent will not differentiate between 3-butenal and 2-butanone?
a) Br2/CCl4
b) Ag2O,OH–
c) H2NNHC6H5
d) KMnO4,OH–
e) None of these choices.
Topic: Reagents
Section: 16.8
Difficulty Level: Medium
52) The compound 
is produced by the reaction of an excess of benzaldehyde with which compound?
a) Ammonia
b) Hydrazine
c) Nitrogen
d) Phenylhydrazine
e) Hydroxylamine
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-
Topic: Mechanisms
Section: 16.12
Difficulty Level: Medium
54) Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound(s)?
a) 
b) 
c) C6H5C(OCH3)3
d) and
e) and C6H5C(OCH3)3
Topic: Reaction Products
Section: 16.7
Difficulty Level: Easy
55) Select the structure of the major product in the following reaction.
a) Ethylbenzene
b) 1-Phenylethanol
c) Acetophenone
d) 2-Phenylethanal
e) Vinylbenzene
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium
56) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
57) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
58) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
59) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
60) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
61) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
62) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
63) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium
64) What is the final product, Z, of the following synthesis?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium
65) Select the structure of the major product in the following reaction.
a) Ethylbenzene
b) 1-Phenylethanol
c) Acetophenone
d) 2-Phenylethanal
e) Vinylbenzene
Topic: Reaction Products
Section: 16.5
Difficulty Level: Medium
66) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5
Difficulty Level: Medium
67) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5
Difficulty Level: Medium
68) Select the structure of the major product in the following reaction.
a) cyclopentanol
b) 1-cyclopentylcyclopentane
c) cyclopentanone
d) cyclopentene
e) 1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane
Topic: Reaction Products
Section: 16.5
Difficulty Level: Medium
69) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium
70) The product, K, of the following sequence of reactions 
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.6
Difficulty Level: Medium
71) The product, K, of the following sequence of reactions would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.6
Difficulty Level: Medium
72) The product, J, of the following sequence of reactions would be:
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Reaction Products
Section: 16.5 and 16.6
Difficulty Level: Medium
73) The product, E, of the following sequence of reactions
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.7
Difficulty Level: Medium
74) The product, C, of the following sequence of reactions
would be:
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Reaction Products
Section: 16.5 and 16.12
Difficulty Level: Medium
75) The product, E, of the following sequence of reactions
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.7
Difficulty Level: Medium
76) The product, C, of the following reaction sequence, 
would be:
a) 
b) CH3CH2COOCH3
c)
d) CH3CH=CHCOOH
e) None of these choices.
Topic: Reaction Products
Section: 16.9
Difficulty Level: Medium
77) The product, D, of the following reaction sequence, would be:
a) 
b) CH3CH2COOCH3
c) 
d) CH3CH=CHCOOH
e)
Topic: Reaction Products
Section: 16.9
Difficulty Level: Medium
78) What is the major product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.9
Difficulty Level: Medium
79) What is the major product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.9
Difficulty Level: Medium
80) What is the major product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.9
Difficulty Level: Medium
81) The product, H, of the following reaction sequence, 
would be:
a) 
b) 
c) 
d) C6H5CH2CH=CHC6H5
e) 
Topic: Reaction Products
Section: 16.10
Difficulty Level: Medium
82) What would be the final product?
a) 
b) 
c) C6H5CH=CHCH3
d) 
e) 
Topic: Reaction Products
Section: 16.10
Difficulty Level: Medium
83) What would be the final product?
a) 
b) 
c) C6H5CH=CHCH3
d) 
e) 
Topic: Reaction Products
Section: 16.10
Difficulty Level: Medium
84) What is the reactant W in the synthesis given below?
a) Cyclopentanone
b) Cyclopentene
c) Cyclopentanol
d) Bromocyclopentane
e) Triphenylphosphine oxide
Topic: Reaction Products
Section: 16.10
Difficulty Level: Medium
85) Predict the major organic product of the following reaction:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.12
Difficulty Level: Medium
86) The product, H, of the following reaction sequence,
would be:
a) 
b) 
c) 
d) C6H5CH2CH=CHC6H5
e) 
Topic: Reaction Products
Section: 16.10
Difficulty Level: Hard
87) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.7
Difficulty Level: Hard
88) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.9 and 16.5
Difficulty Level: Hard
89) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.8
Difficulty Level: Hard
90) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.9 and 16.5
Difficulty Level: Hard
91) What would be the product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.8
Difficulty Level: Hard
92) The product, E, of the following reaction sequence, 
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5
Difficulty Level: Hard
93) The product, D, of the following sequence of reactions
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 15.9 and 16.5
Difficulty Level: Hard
94) The product, E, of the following reaction sequence,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5
Difficulty Level: Hard
95) What is the final product of this synthetic sequence?
a) 
b) p-BrC6H4CH2C6H5
c) C6H5CH2COOH
d) 
e) C6H5CH2C6H5
Topic: Reaction Products
Section: 16.5
Difficulty Level: Hard
96) Select the structure of the major product in the following reaction.
a) 4-Methylhexanal
b) 4-Methyl-1-hexanol
c) 3-Methylhexanal
d) 4,10-Dimethyldodecane-6,7-dione
e) 4,10-Dimethyldodecane-6,7-diol
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
97) Select the structure of the major product in the following reaction.
a) 4-Methylhexanal
b) 4-Methyl-1-hexanol
c) 3-Methylhexanal
d) 4,10-Dimethyldodecane-6,7-dione
e) 4,10-Dimethyldodecane-6,7-diol
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
98) Select the structure of the major product in the following reaction.
a) 4-Methylhexanal
b) 4-Methyl-1-hexanol
c) 3-Methylhexanal
d) 4,10-Dimethyldodecane-6,7-dione
e) 4,10-Dimethyldodecane-6,7-diol
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
99) Select the structure of the major product in the following reaction.
a) 3-Methylhexanal
b) 4-Methyl-1-hexanol
c) 4-Methylhexanal
d) 4,10-Dimethyldodecane-6,7-dione
e) 4,10-Dimethyldodecane-6,7-diol
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
100) What new compound will eventually be formed when HCl is added to a solution of pentanal in methanol?
a) 1-Chloro-1-methoxypentane
b) 1,1-Dimethoxypentane
c) 1,1-Dihydroxypentane
d) 1,1-Dichloropentane
e) 1-Chloro-2-methoxypentane
Topic: Reaction Products
Section: 16.7
Difficulty Level: Hard
101) What is the major product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.9
Difficulty Level: Hard
102) What is the major product of the following reaction sequence?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.9
Difficulty Level: Hard
103) Select the structure of the major product in the following reaction.
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4
Difficulty Level: Hard
104) Which of the following reactions would yield benzaldehyde?
a) 
b) 
c) 
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 16.7
Difficulty Level: Easy
105) Which of the following procedures would not yield 3-pentanone as a major product?
a) 
b)
c) 
d)
e) 
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
106) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
107) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
108) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
109) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
110) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
111) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
112) Which synthesis or syntheses would yield propanal?
a) 
b) 
c)
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
113) Which synthesis or syntheses would yield propanal?
a) 
b)
c)
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
114) Which synthesis or syntheses would yield propanal?
a)
b)
c)
d) All of these choices.
e) None of these choices.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
115) Which of the reactions listed below would serve as a synthesis of acetophenone,
a)
b) 
c) 
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
116) Which of the reactions listed below would serve as a synthesis of acetophenone,
a)
b) 
c) 
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
117) Which of the following would yield 3-pentanone as the major product?
a) 
b)
c)
d) Two of these choices.
e) All of these choices.
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
118) Which sequence of reactions would be utilized to convert
a) 2 CH3MgBr, then NH4+
b) HOCH2CH2OH, H3O+; LiAlH4, ether; 2 CH3MgBr, then NH4+
c) HOCH2CH2OH, H3O+; 2 CH3MgBr, then NH4+
d) HOCH2CH2OH, H3O+; H2, Pt; CH3OH, NH4+
e) None of these choices.
Topic: Synthesis
Section: 16.7
Difficulty Level: Medium
119) Which of the following procedures would not yield 
as a product?
a) I
b) II
c) III
d) IV
e) V
Topic: Synthesis
Section: 16.4 and 16.7
Difficulty Level: Medium
120) Which reaction sequence would be used to prepare
a) I
b) II
c) III
d) IV
e) All of these choices would yield the product.
Topic: Synthesis
Section: 16.10
Difficulty Level: Medium
121) Which Wittig reagent would be used to synthesize
a) I
b) II
c) III
d) IV
e) Either I or II could be used.
Topic: Synthesis
Section: 16.10
Difficulty Level: Medium
122) Which of the following is not a synthesis of benzophenone,
a) 
b) 
c) 
d)
e) All of these choices will give benzophenone.
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
123) Which of the following is not a synthesis of benzophenone,
a) 
b) 
c) 
d)
e) All of these choices will give benzophenone.
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
124) Which of the following is not a synthesis of benzophenone,
a) 
b)
c) 
d)
e) All of these choices will give benzophenone.
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
125) Which of the following is a synthesis of 3-heptanone?
a)
b) 
c) 
d)
e) All of these choices are syntheses of 3-heptanone.
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
126) Which of the following is a synthesis of 3-heptanone?
a)
b) 
c) 
d)
e) All of these choices are syntheses of 3-heptanone.
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
127) What, in general, is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents?
a) I > III > IV> II > V
b) IV > II > I > III > V
c) V > III > I > II > IV
d) I > IV > II > III > V
e) III > V > IV > II > I
Topic: Carbonyl Reactivity
Section: 16.6
Difficulty Level: Medium
128) Which of these gem-diols is expected to be the most stable?
a) 
b) CH3CH(OH)2
c) 
d) C6H5CH(OH)2
e) ClCH2CH(OH)2
Topic: Carbonyl Reactivity
Section: 16.7
Difficulty Level: Medium
129) Which of these gem-diols is expected to be the least stable?
a) 
b) CH3CH(OH)2
c) 
d) C6H5CH(OH)2
e) ClCH2CH(OH)2
Topic: Carbonyl Reactivity
Section: 16.7
Difficulty Level: Medium
130) What, in general, is the order of increasing reactivity of these carbonyl compounds towards nucleophilic reagents?
a) I < III < V < II < IV
b) IV < II < I < III < V
c) V < III < I < II < IV
d) II < I < V < III < IV
e) III < V < IV < II < I
Topic: Carbonyl Reactivity
Section: 16.6
Difficulty Level: Medium
131) Which of the following compounds is an acetal?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: New Functional Groups
Section: 16.7
Difficulty Level: Easy
132) Which is the general formula for a thioacetal?
a) 
b) 
c) 
d) 
e) 
Topic: New Functional Groups
Section: 16.7
Difficulty Level: Easy
133) Which compound is an acetal?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: New Functional Groups
Section: 16.7
Difficulty Level: Easy
134) Which compound is a hemiacetal?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: New Functional Groups
Section: 16.7
Difficulty Level: Easy
135) Which of the following is formed when 3-methylcyclopentanone reacts with hydroxylamine?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions of Aldehydes and Ketones
Section: 16.8
Difficulty Level: Medium
136) Which of the following is formed when 4-methylpentanal reacts with phenylhydrazine?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions of Aldehydes and Ketones
Section: 16.8
Difficulty Level: Medium
137) Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with hydroxylamine?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions of Aldehydes and Ketones
Section: 16.8
Difficulty Level: Medium
138) Which of the following is formed when 2,2,3-trimethylcyclohexanone reacts with hydrazine?
a) I
b) II
c) III
d) IV
e) V
Topic: Reactions of Aldehydes and Ketones
Section: 16.8
Difficulty Level: Medium
139) A compound with formula C5H10O gives two signals only, both singlets, in the 1H NMR spectrum. Which of these structures is a possible one for this compound?
a)
b)
c)
d)
e)
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
140) A compound with formula C5H10O gives two signals only, one a triplet and the other a quartet, in the 1H NMR spectrum. Which of these structures is a possible one for this compound?
a) 
b) 
c) 
d) 
e) 
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
141) The 1H NMR spectrum of a compound with formula C7H14O gives three signals. Which of these structures is a possible one for this compound?
a) 2-Heptanone
b) 3-Heptanone
c) 2,4-Dimethyl-3-pentanone
d) 2,2-Dimethyl-3-pentanone
e) Two of these choices.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
142) The 1H NMR spectrum of a compound with formula C7H14O gives two signals. Which of these structures is a possible one for this compound?
a) 2-Heptanone
b) 3-Heptanone
c) 2,4-Dimethyl-3-pentanone
d) 2,2-Dimethyl-3-pentanone
e) Two of these choices.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
143) The 13C NMR spectrum of a compound with formula C7H14O gives three signals. Which of these structures is a possible one for this compound?
a) 2-Heptanone
b) 3-Heptanone
c) 2,2-Dimethyl-3-pentanone
d) 2,4-Dimethyl-3-pentanone
e) Two of these choices.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
144) The 13C NMR spectrum of a compound with formula C7H14O gives five signals. Which of these structures is a possible one for this compound?
a) 2-Heptanone
b) 3-Heptanone
c) 2,2-Dimethyl-3-pentanone
d) 2,4-Dimethyl-3-pentanone
e) Two of these choices.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
145) The 1H NMR spectrum of a compound with formula C7H14O gives a doublet at 9.2 ppm. Which of these structures is a possible one for this compound?
a) 2-Methyl-3-hexanone
b) 2-Methylhexanal
c) 2,2-Dimethylpentanal
d) 2,2-Dimethyl-3-pentanone
e) Two of these choices.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
Question type: Molecular Drawing
146) Suggest a synthetic strategy for the synthesis of 4-methylpentanal from 3-methyl-1-bromobutane.
Topic: Synthetic Strategy
Section: 16.4
Difficulty Level: Medium
147) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-bromobutane.
Topic: Synthetic Strategy
Section: 16.5
Difficulty Level: Medium
148) Suggest a synthetic strategy for the synthesis of 6-methyl-3-heptanol from 4-methylpentanenitrile, (CH3)2CHCH2CH2CN.
Topic: Synthetic Strategy
Section: 16.5
Difficulty Level: Hard
149) Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene.
Topic: Synthetic Strategy
Section: 16.5
Difficulty Level: Hard
150) cis-Stilbene (cis-1,2-diphenylethene) can be prepared in high yield from its trans diastereomer. Propose a reasonable synthesis.
Topic: Synthetic Strategy
Section: 16.10
Difficulty Level: Hard
151) Complete the following reaction sequence, giving structural details of all significant intermediates and the final product.
Topic: Reaction Sequence
Section: 16.7
Difficulty Level: Medium
152) In the total synthesis of the Cecropia juvenile hormone, the following sequence of reactions were used. Draw the intermediate and final product formed.
Topic: Reaction Sequence
Section: 16.7
Difficulty Level: Hard
153) Complete the following reaction sequence, giving structural details of all significant intermediates.
Topic: Reaction Sequence
Section: 16.7
Difficulty Level: Hard
154) Complete the following reaction sequence, giving structural details of all significantintermediates and the final product.
Topic: Reaction Sequence
Section: 16.7
Difficulty Level: Hard
155) Complete the following reaction sequence, giving structural details of all significant intermediates X, Y, and final product Z.
Topic: Reaction Sequence
Section: 16.4
Difficulty Level: Hard
156) Complete the following reaction sequence, giving structural details of all significant intermediates.
Topic: Reaction Sequence
Section: 16.5
Difficulty Level: Hard
157) Complete the following reaction sequence, giving structural details of all significant intermediates.
Topic: Reaction Sequence
Section: 16.5
Difficulty Level: Hard
158) Complete the following reaction sequence, giving structural details of all significant intermediates and the final product.
Topic: Reaction Sequence
Section: 16.5
Difficulty Level: Hard
159) Complete the following reaction sequence, giving structural details of all significant intermediates and the final product.
Topic: Reaction Sequence
Section: 16.5 and 16.12
Difficulty Level: Hard
Question type: Essay
160) Aldehydes are more reactive than ketones towards nucleophilic substitution because of both steric and electronic factors. Briefly explain.
a) Steric reasons: ___.
b) Electronic reasons: ___.
b) aldehydes have only one electron-releasing group to partly neutralize/stabilize the partial positive charge at the carbonyl carbon while ketones have two
Topic: Relative Reactivity
Section: 16.6
Difficulty Level: Medium
Question type: fill-in-the-blank
161) A compound with an OH and OR group attached to the same carbon is known as a(n) ___.
Topic: Hemiacetals
Section: 16.7
Difficulty Level: Easy
162) A compound with two OH groups attached to the same carbon is known as a(n) ___.
Topic: Hydrates
Section: 16.7
Difficulty Level: Easy
163) A compound with two OR groups attached to the same carbon is known as a(n) ___.
Topic: Acetals
Section: 16.7
Difficulty Level: Easy
164) A compound with an OH and CN group attached to the same carbon is known as a(n) ___.
Topic: Cyanohydrins
Section: 16.9
Difficulty Level: Easy
165) A compound containing a C=N double bond is known as a(n) ___.
Topic: Imines
Section: 16.8
Difficulty Level: Easy
166) 2,4-DNP is a reagent frequently used for functional group tests; it detects the presence of ___.
Topic: Functional Group Tests
Section: 16.8
Difficulty Level: Easy
167) Oximes are formed when aldehydes and ketones react with ___.
Topic: Functional Group Tests
Section: 16.8
Difficulty Level: Easy
168) The reaction between a phosphorus ylide and an aldehyde or ketone is called the ___ reaction.
Topic: Wittig Reaction
Section: 16.10
Difficulty Level: Easy
169) The driving force for the Wittig reaction is the formation of the very strong ___ bond in ___.
Topic: Wittig Reaction
Section: 16.10
Difficulty Level: Easy
170) The conversion of a trans epoxide to a cis alkene using triphenylphosphine is an example of a ___ reaction.
Topic: General
Section: 16.10
Difficulty Level: Hard
171) The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example of a ___ reaction.
Topic: General
Section: 16.10
Difficulty Level: Hard
Question type: Molecular Drawing
172) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation:
Topic: Mechanisms
Section: 16.8
Difficulty Level: Medium
173) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation:
Topic: Mechanisms
Section: 16.10
Difficulty Level: Hard
174) Draw a complete mechanism, using arrow convention to indicate electron movement, for the following transformation:
Topic: Mechanisms
Section: 16.10
Difficulty Level: Hard
Question type: fill-in-the-blank
175) The Tollens’ test, used in conjunction with 2,4-DNP, can distinguish between ___ and ___.
Topic: Functional Group Tests
Section: 16.13
Difficulty Level: Easy
Question type: Essay
176) What reagent would help you distinguish between acetophenone and 2-methylbenzaldehyde?
Topic: Functional Group Tests
Section: 16.13
Difficulty Level: Easy
177) Explain clearly how you might use 1H NMR to distinguish between 2-phenylacetaldehyde and acetophenone.
2-Phenylacetaldehyde Acetophenone
C6H5CH2CHO and C6H5COCH3
3 signals 2 signals
approximate ppm approximate ppm
doublet (-CH2-) 2.5 singlet (-CH3) 2.0
multiplet (C6H5) 7 multiplet (C6H5) 7.2
triplet(-CHO) 9
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
178) Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1720 cm−1
1H NMR: 1.9 δ (triplet, 3H), 1.7 δ (sextet, 2H), 2.1 δ (singlet, 3H), 2.4 δ (triplet, 2H)
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
179) Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1720 cm−1
1H NMR: 1.1 δ (triplet, 3H), 2.4 δ (quartet, 2H)
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
180) Propose a structure that fits the following spectroscopic data:
C9H10O
IR: 1680 cm−1
1H NMR: 1.25 δ (triplet, 3H), 3.0 δ (quartet, 2H), 7-8 δ (complex multiplet, 5H)
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
181) Propose a structure that fits the following spectroscopic data:
C7H6O
IR: 1703 cm−1
1H NMR: 7-8 δ (complex multiplet, 5H), 10.0 δ (singlet, 1H)
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
182) Propose a structure that fits the following spectroscopic data:
C3H6O
IR: 1730 cm−1
1H NMR: 1.1 δ (triplet, 3H), 2.5 δ (doublet of quartets, 2H), 9.8 δ (doublet, 1H)
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
183) Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1716 cm−1
Broadband decoupled 13C NMR: 7.93, 35.50, 212.07 δ
DEPT experiments show: signal at 7.93 δ as CH3 and signal at 35.50 δ as CH2
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
184) Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1717 cm−1
Broadband decoupled 13C NMR: 13.70, 17.41, 29.78, 45.71, 208.93 δ
DEPT experiments show: signals at 13.70, 29.78 δ as CH3 and signals at 17.41, 45.71 δ as CH2
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
185) Propose a structure that fits the following spectroscopic data:
C4H8O
IR: 1728 cm−1
Broadband decoupled 13C NMR: 13.71, 15.69, 45.82, 202.80 δ
DEPT experiments show: signal at 13.71 δ as CH3 and signals at 15.69, 45.82 δ as CH2
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
186) Propose a structure that fits the following spectroscopic data:
C6H12O
IR: 1708 cm−1
Broadband decoupled 13C NMR: 24.61, 26.42, 44.31, 213.81 δ
DEPT experiments show: signals at 24.61, 26.42 δ as CH3
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
187) Propose a structure that fits the following spectroscopic data:
C4H8O
IR: 1737 cm−1
Broadband decoupled 13C NMR: 15.48, 41.07, 204.86 δ
DEPT experiments show: signal at 41.07 δ as CH and signal at 15.48 δ as CH3
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
188) Propose a structure that fits the following spectroscopic data:
C5H10O
IR: 1728 cm−1
Broadband decoupled 13C NMR: 22.59, 23.57, 52.66, 202.71 δ
DEPT experiments show: signal at 23.57 δ as CH, signal at 22.59 δ as CH3, and signal at 52.66 δ as CH2.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
189) Acetaldehyde is reacted with excess methanol in acid. The product was isolated and gave the following 1H NMR spectroscopic data:
1.3 δ (doublet, 3H)
3.4 δ (singlet, 6H)
4.6 δ (quartet, 1H)
Propose a structure consistent with this information.
Topic: Spectroscopy
Section: 16.13
Difficulty Level: Medium
190) Which of the compounds listed below would you expect to have the lowest boiling point? (They all have approximately the same molecular weight.)
a) Pentane
b) 1-Butanol
c) Butanal
d) 1-Fluorobutane
e) Diethyl ether
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.3
Difficulty Level: Easy
191) What is the major product of the following reaction?
a) 1,1-diphenylmethanol
b) 1,2 -diphenylethanol
c) 3-methylbutanal
d) 1-phenylbutanal
e) 1-methylbutanal
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.9
Difficulty Level: Medium
192) What is the major product of the following reaction?
a) 1,1-diphenylmethanol
b) 1,2 -diphenylethanol
c) 3-methylbutanal
d) 1-phenylbutanal
e) 1-methylbutanal
Topic: Physical Properties, Relationships, Stereochemistry
Section: 16.9
Difficulty Level: Medium
193) Which statement about the relationship between the following compounds is true?
and
a) the compound on the left is a hemiacetal; the compound on the right is an acetal
b) the compound on the left is an acetal; the compound on the right is a hemiacetal
c) the compound on the left is a hemiacetal; the compound on the right is an ester
d) the compound on the left is an ester; the compound on the right is a hemiacetal
e) the compound on the left is an ester; the compound on the right is an acetal
Topic: Reaction Products
Section: 16.7
Difficulty Level: Easy
194) Which statement about the relationship between the following compounds is true?
and C6H5CH(OCH3)2
a) the compound on the left is a hemiacetal; the compound on the right is an acetal
b) the compound on the left is an acetal; the compound on the right is a hemiacetal
c) the compound on the left is a hemiacetal; the compound on the right is an ester
d) the compound on the left is an ester; the compound on the right is a hemiacetal
e) the compound on the left is an ester; the compound on the right is an acetal
Topic: Reaction Products
Section: 16.7
Difficulty Level: Easy
195) Which statement about the relationship between the following compounds is true?
and C6H5CH(OH)OCH3
a) the compound on the left is a hemiacetal; the compound on the right is an acetal
b) the compound on the left is an acetal; the compound on the right is a hemiacetal
c) the compound on the left is a hemiacetal; the compound on the right is an ester
d) the compound on the left is an ester; the compound on the right is a hemiacetal
e) the compound on the left is an ester; the compound on the right is an acetal
Topic: Reaction Products
Section: 16.7
Difficulty Level: Easy
196) What is the product, X, of the following synthesis?
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.4
Difficulty Level: Medium
197) The product, J, of the following sequence of reactions would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.6
Difficulty Level: Medium
198) The product, I, of the following sequence of reactions would be:
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Reaction Products
Section: 16.5 and 16.6
Difficulty Level: Medium
199) The product, B, of the following sequence of reactions
would be:
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Reaction Products
Section: 16.5 and 16.12
Difficulty Level: Medium
200) The product, B, of the following sequence of reactions
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5 and 16.7
Difficulty Level: Medium
201) The product, D, of the following reaction sequence, would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5
Difficulty Level: Hard
202) The product, D, of the following reaction sequence,
would be:
a) I
b) II
c) III
d) IV
e) V
Topic: Reaction Products
Section: 16.5
Difficulty Level: Hard
203) A good synthesis of
a) I
b) II
c) III
d) IV
e) All of these are equally useful.
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
204) What is the major product of the following reaction?
a) benzyl alcohol
b) benzaldehyde
c) benzoic acid
d) benzene
e) toluene
Topic: Synthesis
Section: 16.7
Difficulty Level: Easy
205) What is the major product of the following reaction?
a) benzyl alcohol
b) benzaldehyde
c) benzoic acid
d) benzene
e) toluene
Topic: Synthesis
Section: 16.7
Difficulty Level: Easy
206) What is the major product of the following reaction?
a) benzyl alcohol
b) benzaldehyde
c) benzoic acid
d) benzene
e) toluene
Topic: Synthesis
Section: 16.7
Difficulty Level: Easy
207) What is the major product of the following reaction?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) propanoic acid
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
208) What is the major product of the following reaction?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) propanoic acid
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
209) What is the major product of the following reaction?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) propanoic acid
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
210) What is the major product of the following reaction?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) propanoic acid
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
211) What is the major product of the following reaction?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) propanoic acid
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
212) What is the major product of the following reaction?
a) propanal
b) 2-propanone
c) propanoic acid
d) propanol
e) chloropropane
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
213) What is the major product of the following reaction?
a) propanal
b) 2-propanone
c) propanoic acid
d) propanol
e) chloropropane
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
214) What is the major product of the following reaction?
a) propanal
b) 2-propanone
c) propanoic acid
d) propanol
e) chloropropane
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
215) What is the major product of the following reaction?
a) propanal
b) 2-propanone
c) propanoic acid
d) propanol
e) chloropropane
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
216) What is the major product of the following reaction?
a) propanal
b) 2-propanone
c) propanoic acid
d) propanol
e) chloropropane
Topic: Synthesis
Section: 16.4
Difficulty Level: Medium
217) What is the major product of the following reaction?
a) acetophenone
b) benzaldehyde
c) benzoic acid
d) benzyl alcohol
e) toluene
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
218) What is the major product of the following reaction?
a) acetophenone
b) benzaldehyde
c) benzoic acid
d) benzyl alcohol
e) toluene
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
219) What is the major product of the following reaction?
a) acetophenone
b) benzaldehyde
c) benzoic acid
d) benzyl alcohol
e) toluene
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
220) What is the major product of the following reaction?
a) acetophenone
b) benzaldehyde
c) benzoic acid
d) benzyl alcohol
e) toluene
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
221) Which of the following would yield 3-pentanone as the major product?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) pentane
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
222) Which of the following would yield 3-pentanone as the major product?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) pentane
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
223) Which of the following would yield 3-pentanone as the major product?
a) 3-pentanone
b) 2-pentanone
c) pentanal
d) pentanoic acid
e) pentane
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
224) What is the major product of the following reaction?
a) benzophenone
b) acetophenone
c) benzaldehyde
d) benzoic acid
e) benzyl alcohol
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
225) What is the major product of the following reaction?
a) benzophenone
b) acetophenone
c) benzaldehyde
d) benzoic acid
e) benzyl alcohol
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
226) What is the major product of the following reaction?
a) benzophenone
b) acetophenone
c) benzaldehyde
d) benzoic acid
e) benzyl alcohol
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
227) What is the major product of the following reaction?
a) benzophenone
b) acetophenone
c) benzaldehyde
d) benzoic acid
e) benzyl alcohol
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
228) What is the major product of the following reaction?
a) benzophenone
b) acetophenone
c) benzaldehyde
d) benzoic acid
e) benzyl alcohol
Topic: Synthesis
Section: 16.5
Difficulty Level: Medium
229) What is the major product of the following reaction?
a) 3-heptanone
b) 2-heptanone
c) heptanal
d) 3-hexanone
e) 2-hexanone
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
230) What is the major product of the following reaction?
a) 3-heptanone
b) 2-heptanone
c) heptanal
d) 3-hexanone
e) 2-hexanone
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
231) What is the major product of the following reaction?
a) 3-heptanone
b) 2-heptanone
c) heptanal
d) 3-hexanone
e) 2-hexanone
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
232) What is the major product of the following reaction?
a) 3-heptanone
b) 2-heptanone
c) heptanal
d) 3-hexanone
e) 2-hexanone
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard
233) What is the major product of the following reaction?
a) 3-heptanone
b) 2-heptanone
c) heptanal
d) 3-hexanone
e) 2-hexanone
Topic: Synthesis
Section: 16.5
Difficulty Level: Hard