Download CHEM 121. Chapter 15

CHEM 121. Chapter 15 Name: __________________________ Date: _____________
1. Which of the following structural features is common to both aldehydes and ketones?
A)
B)
C)
D)
2. Which of the following structural features is possessed by aldehydes but not ketones?
A) At least one hydrogen atom is bonded to the carbonyl carbon atom.
B) At least one hydroxyl group is bonded to the carbonyl carbon atom.
C) The carbonyl carbon atom is bonded to two other carbon atoms.
D) The carbonyl carbon atom is part of a ring structure.
3. Which of the following statements concerning aldehydes and ketones is correct?
A) cyclic aldehydes exist
B) cyclic ketones exist
C) both cyclic aldehydes and cyclic ketones exist
D) neither cyclic ketones nor cyclic aldehydes exist
4. The simplest aldehyde and ketone contain, respectively, how many carbon atoms?
A) 1 and 1
B) 1 and 3
C) 2 and 2
D) 2 and 3
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O
5. The IUPAC name for the compound CH3 CH2 C
A) acetaldehyde.
B) propionaldehyde.
C) 1-ethanal.
D) propanal.
O
H is
CH3
6. The IUPAC name for the compound CH3 C CH2 CH CH3 is
A) 2-methyl-2-pentanone.
B) 2-methyl-4-pentanone.
C) 4-methyl-2-pentanone.
D) 2-methyl-4-pentaketone.
7. What is the IUPAC name of the aldehyde whose common name is propionaldehyde?
A) propanal
B) methanal
C) ethanal
D) 2-methylbutanal
8. Two other acceptable names for the compound acetone are
A) propanone and diethyl ketone.
B) ethanone and methyl ethyl ketone.
C) propanone and dimethyl ketone.
D) ethanone and diethyl ketone.
9. How many saturated noncyclic six-carbon ketones are there?
A) two
B) four
C) six
D) eight
10. What two functional groups are never found at the end of a carbon chain?
A) alcohol and aldehyde
B) ether and aldehyde
C) alcohol and ketone
D) ether and ketone
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11. Which of the following statements concerning hydrogen bonding is correct?
A) ketone molecules can hydrogen bond to each other
B) aldehyde molecules can hydrogen bond only to other aldehyde molecules
C) both ketone molecules and aldehyde molecules can hydrogen bond to each other
D) aldehyde molecules cannot hydrogen bond to other aldehyde molecules
12. Comparison of the boiling points of aldehydes and ketones with those of other
compounds of similar molecular mass shows that they are
A) lower than those of alkanes and alcohols
B) higher than those of alcohols and alkanes
C) higher than those of alcohols but lower than those of alkanes
D) higher than those of alkanes
13. Which of the following statements concerning the oxidation of aldehydes and ketones is
correct?
A) ketones are resitant to oxidation and aldehydes readily undergo oxidation
B) ketones readily undergo oxidation
C) both aldehydes and ketones readily undergo oxidation
D) both aldehydes and ketones are resistant to oxidation
14. Which of the following statements concerning the oxidation of aldehydes and ketones is
correct?
A) Aldehydes readily undergo oxidation and ketones are resistant to oxidation.
B) Ketones readily undergo oxidation and aldehydes are resistant to oxidation.
C) Both aldehydes and ketones readily undergo oxidation.
D) Both aldehydes and ketones are resistant to oxidation.
15. The oxidizing agent in the Tollen's test for the presence of an aldehyde is
A) Ag+
B) Ag
C) Cu2+
D) Cu2O
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O
16. What is the product when CH3 C CH3 is reduced using H2 gas and a Ni catalyst?
A)
B)
C)
D)
17. When an alcohol molecule adds across a carbon-oxygen double bond of an aldehyde or
ketone, the
A) H atom from the alcohol bonds to the carbonyl carbon atom.
B) OH portion from the alcohol bonds to the carbonyl oxygen atom.
C) OR portion from the alcohol bonds to the carbonyl carbon atom.
D) OH portion from the alcohol bonds to the carbonyl carbon atom.
18. A hemiacetal is a compound in which
A) a hydroxy group and an alkoxy group are attached to the same carbon atom.
B) a hydroxyl group and an alkoxy group are attached to adjacent carbon atoms.
C) two alkoxy groups are attached to the same carbon atom.
D) two alkoxy groups are attached to adjacent carbon atoms.
19. The structural difference between a hemiacetal and an acetal is the replacement of a
A) –OH group with an –OR group.
B) H atom with an –OR group.
C) H atom with a –OH group.
D) –OR group with a –OH group.
20. Hydrolysis of an acetal in an acid solution would yield
A) an aldehyde, a ketone, and one alcohol.
B) an aldehyde, a ketone, and two alcohols.
C) an aldehyde or a ketone and one alcohol.
D) an aldehyde or a ketone and two alcohols.
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21. Which of the following statements concerning a carbonyl group is incorrect?
A) It is polar.
B) It contains two oxygen atoms and one carbon atom.
C) It is present in both aldehydes and ketones.
D) more than one correct response
E) no correct response
22. Which of the following is a correct notation for the aldehyde functional group?
A)
B)
C)
D) more than one correct response
E) no correct response
23. Which of the following aldehydes is paired with an incorrect IUPAC name?
A)
B)
C)
D) more than one correct response
E) no correct response
24. Which of the following pairings of aldehyde common and IUPAC names is correct?
A) acetaldehyde and methanal
B) 2-methylbutyraldehyde and 2-methylbutanal
C) formaldehyde and ethanal
D) more than one correct response
E) no correct response
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25. Which of the following pairings of ketone IUPAC and common names is correct?
A) 2-methyl-3-pentanone and methyl propyl ketone
B) 3-methyl-2-pentanone and isopropyl methyl ketone
C) propanone and dimethyl ketone
D) more than one correct response
E) no correct response
26. Which of the following compounds is a constitutional isomer of 2-pentanone?
A) 3-methyl-2-pentanone
B) 3-methyl-2-butanone
C) isopropyl methyl ketone
D) more than one correct response
E) no correct response
27. Which of the following compounds contains 7 carbon atoms?
A) benzaldehyde
B) acetophenone
C) benzophenone
D) more than one correct response
E) no correct response
28. In which of the following pairs of compounds does the first listed compound have a
greater water solubility than the second listed compound?
A) butanal, methanal
B) propanone, 2-pentanone
C) hexanal, 2-butanone
D) more than one correct response
E) no correct response
29. Oxidation of which of the following alcohols will produce a ketone?
A)
B)
C)
D) more than one correct response
E) no correct response
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30. Which of the following compounds would be resistant to oxidation with a mild
oxidizing agent?
A)
B)
C)
D) more than one correct response
E) no correct response
31. Hydrogenation, with a catalyst, of which of the following compounds would produce a
four-carbon alcohol?
A) butanal
B) 2-butanone
C) diethylketone
D) more than one correct response
E) no correct response
32. In which of the following pairings of compound types does the first listed compound
type contain more alkoxy groups than the second listed compound type?
A) acetal, hemiacetal
B) hemiacetal, acetal
C) aldehyde, hemiacetal
D) more than one correct response
E) no correct response
33. Which of the following is a product of the acid hydrolysis of the following compound?
OH
CH3 CH2 C H
O CH3
A)
B)
C)
D)
E)
methyl alcohol
ethyl alcohol
propanone
more than one correct response
no correct response
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34. Which of the following types of compounds contains a carbon-sulfur double bond?
A) a thial (thioaldehyde)
B) a thione (thioketone)
C) a sulfoxide
D) more than one correct response
E) no correct response
35. Which of the following compounds would be named as a ketone?
A)
B)
C)
D) more than one correct response
E) no correct response
Use the following to answer questions 36-45:
In each of the following multiple-choice questions, characterize EACH of the three given
statements as being TRUE or FALSE and then indicate the collective true-false status of the
statements using the choices
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.
36. Statements:
(1) Cyclic hemiacetals are usually more stable than noncyclic hemiacetals.
(2) A carbonyl group consists of a carbon atom and an oxygen atom joined by a double
bond.
(3) The compound benzaldehyde contain six carbon atoms.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
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37. Statements:
(1) The simplest aldehyde is formaldehyde and the simplest ketone is acetone.
(2) Carbonyl group polarity makes dipole-dipole interactions between like aldehyde
molecules or like ketone molecules possible.
(3) Reaction of a hemiacetal with an alcohol produces an acetal.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
38. Statements:
(1) Aldehydes and ketones readily undergo oxidation to carboxylic acids.
(2) Propanone and dimethyl ketone are two names for the same compound.
(3) The “silver mirror test” distinguishes between aldehydes and ketones.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
39. Statements:
(1) Acetals contain three oxygen atoms and hemiacetals contain two oxygen atoms.
(2) Reduction of an aldehyde, using hydrogen gas, produces a primary alcohol.
(3) In an aldehyde, the carbonyl group can be located on either carbon 1 or carbon 2.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
40. Statements:
(1) In a “dial” two aldehyde groups are present.
(2) Formaldehyde readily participates in polymer formation.
(3) Primary alcohol oxidation is a method for producing ketones.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
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41. Statements:
(1) Butanal and 2-butanone are constitutional isomers.
(2) The linear notation for an aldehyde is RCOH and that for a ketone is RCOR.
(3) Water molecules can hydrogen bond with aldehyde and ketone molecules.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
42. Statements:
(1) The compound 4-oxopentanal contains both an aldehyde and an ether functional
group.
(2) An alkoxy group and a hydroxy group attached to the same carbon atom are present
in both hemiacetals and acetals.
(3) Cyclic aldehyde structures are possible but cyclic ketone structures are not possible.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
43. Statements:
(1) Butanal and butanone are both correct IUPAC names.
(2) The two alcohol molecules produced when an acetal molecule undergoes hydrolysis
are always identical.
(3) Aldehydes and ketones are both classified as carbonyl-containing compounds.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
44. Statements:
(1) In the IUPAC nomenclature system, an aldehyde group has priority over a ketone
group.
(2) Addition of an alcohol molecule across the carbon-oxygen double bond of an
aldehyde produces a compound in which the carbonyl carbon atom bears both an alkoxy
group and a hydroxy group.
(3) 2-Propenal contains two fewer hydrogen atoms than propionaldehyde.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
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45. Statements:
(1) The lachrymator in wood smoke is formaldehyde.
(2) The skin pigment melanin is a polymeric substance containing many interconnected
aldehyde units.
(3) Benedict's test can be used to detect glucose in urine (diabetes) because glucose
contains an aldehyde group.
A) All three statements are true.
B) Two of the three statements are true.
C) Only one of the statements is true.
D) None of the statements is true.
Use the following to answer questions 46-50:
Characterize each compound in terms of functional groups present using the response list.
Responses may be used more than once or need not be used at all.
a) one aldehyde functional group
b) two aldehyde functional groups
c) one ketone functional group
d) one aldehyde and one ketone functional group
46. Pentanal
47. 3-Pentanone
48. Pentanedial
49. 3-Methylpentanone
50. 3-Oxopentanal
Use the following to answer questions 51-55:
For each pair of compounds, select a correct characterization from the response list. Responses
may be used more than once or need not be used at all.
a) have the same molecular formula but are different compounds
b) both contain a carbon ring system
c) contain the same number of carbon atoms but have different molecular formulas
d) two names for the same compound
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51. Acetone Propanal
52. Heptanal Benzaldehyde
53. Diethylketone Pentanal
54. Acetaldehyde Ethanal
55. 2,2-DimethylbutanaCyclohexanone
Use the following to answer questions 56-60:
For each of the compound characterizations, select from the response list the number of
constitutional isomers that exist. Responses may be used more than once or need not be used at
all.
a) two
b) three
c) four
d) five
56. Saturated four-carbon aldehyde
57. Saturated four-carbon monochloroaldehyde
58. Methylcyclohexanone
59. Saturated noncyclic five-carbon ketone
60. Molecular formula of C4H8O
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Use the following to answer questions 61-66:
For each set of reactants, select a correct product characterization from the response list.
Responses may be used more than once or need not be used at all.
a) hemiacetal
b) acetal
c) alkene
d) alcohol
61. Aldehyde Alcohol Acid catalyst
62. Ketone Two alcohols Acid catalyst
63. Hemiacetal Alcohol Acid catalyst
64. Aldehyde Hydrogen Ni catalyst
65. Ketone Hydrogen Ni catalyst
66. Oxidation of
Use the following to answer questions 67-70:
For each of the reaction types, select from the response list the type of organic compound
produced. Responses may be used more than once or need not be used at all.
O
R C
a)
b)
c)
d)
O
H
R C
O
OH
R
R
CH
R
R C
O
R
carboxylic acid
ketone
alcohol
no reaction occurs
67. Oxidation of
68. Oxidation of
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R C
H
69. Reduction of
70. Reduction of
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Answer Key
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2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
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21.
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24.
25.
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27.
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30.
31.
32.
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34.
35.
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37.
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39.
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41.
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43.
44.
C
A
B
B
D
C
A
C
C
D
D
D
A
A
A
C
C
A
A
D
B
A
A
B
C
D
A
B
B
C
D
A
A
D
B
B
A
B
B
B
B
D
C
A
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45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
55.
56.
57.
58.
59.
60.
61.
62.
63.
64.
65.
66.
67.
68.
69.
70.
B
a
c
b
c
d
a
c
a
d
c
a
d
b
b
b
a
b
b
d
d
a
d
b
c
c
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