Exam

Name___________________________________

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the
question.

1) Which one of the following compounds is an aldehyde? 1)

A) CH3 - CH = CH - CH2 - CH3
B) O

CH3 - CH2 - CH
C) CH3 - SH
D) OH
|
CH3 - CH - CH3
E) CH3 - CH2 - O - CH2 - CH3
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-1

2) What are the bond angles in a typical carbonyl group? 2)

A) 109.5° B) 135° C) 90° D) 45° E) 120°
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-2

3) How many carbonyl-containing isomers does the formula C3 H6 O have? 3)

A) eight B) two C) three D) five E) seven
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-3

1
4) The compound 2-propanone is also known as 4)
A) -propanone.
B) propylone.
C) acetone.
D) dimethyl ketone.
E) 2-propanone.
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-4

5) The common name for 2-butanone, a readily available solvent, is 5)

A) butyl ketone.
B) methyl ethyl ketone.
C) -butanone.
D) methyl acetone.
E) butyl ether.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-5

6) Formaldehyde is used industrially to make 6)

A) carpeting.
B) polymers.
C) insulating materials.
D) All of the above.
E) None of the above.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-6

2
7) Acetone can be produced by the body when a person is 7)
A) exercising.
B) dieting with high protein diets.
C) recovering from surgery.
D) sleeping.
E) ill with a flu.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-7

8) Which of the following compounds contains a ketone functional group? 8)

A) CH3
|
CH3 - C - OH
|
CH3

B) O

CH3 - CH

C) O

CH3 - CH2 - C - CH3

D) CH3 - O - CH
|
CH3
E) CH3 - CH2 - O - CH2 -CH3

Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-8

3
 9) What is the IUPAC name for this compound? 9)

CH3 - CH

A) 1-ethanone
B) methanal
C) 1-ethanaldehyde
D) ethanal
E) methyl aldehyde
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-9

10) What is the IUPAC name for this compound? 10)

A) cyclohexyl methyl ketone

B) 1,4-dimethyl-3-cyclohexanone
C) 2,5-dimethylcyclohexanone
D) 1,4-dimethyl-2-cyclohexanone
E) methylcyclohexanone
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-10

4
11) What is the name of this compound? 11)

CH3 - C - CH - CH3
|
CH3

A) 2-methyl-3-ketone butane
B) 3-methyl-2-butanone
C) 2-pentanone
D) 2-methyl-3-butanone
E) methyl propyl ketone
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-11

12) Three functional groups found in this compound are 12)

A) cycloalkene, alcohol, and carboxylic acid.

B) alcohol, ether, and ketone.
C) aldehyde, ether, and carboxylic acid.
D) alcohol, aromatic, and ether.
E) alcohol, aldehyde, and ether.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-12

5
13) Which of the following pairs of compounds are isomers? 13)
A) O O

CH3 -CH2 - C- CH3 and CH3 - CH2 - CH2 -CH

B) CH3 -CH2 -CH2 -OH and CH3 -O-CH3

C) O

CH3 CH2 OH and H C CH3

D)
CH3 -CH2 - O-CH2 -CH3 and CH2 - O - CH2 - CH3
|
CH3

E) OH
|
CH3 -CH2 -CH-OH and CH 3 - CH-CH2 -CH3
|
CH3

Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-13

14) In all aldehydes except formaldehyde, how many hydrogen atoms are bonded to the carbonyl 14)
group?
A) one B) two C) three D) four
Answer: A
Explanation: A)
B)
C)
D)
ID: chem6tl 14.1-14

6
15) How many hydrogen atoms are bonded to the carbonyl group in a ketone? 15)
A) none B) one C) two D) three E) four
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-15

16) The carbonyl group consists of 16)

A) a carbon singly bonded to an oxygen.
B) a carbon singly bonded to an oxygen and the oxygen bonded to a hydrogen.
C) a carbon double bonded to an oxygen.
D) a carbon triply bonded to an oxygen.
E) a carbon singly bonded to an oxygen and the oxygen singly bonded to another carbon.
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-16

17) The oxygen atom in a carbonyl group is ________ the carbon atom. 17)
A) more electronegative than
B) more electropositive than
C) identical in electronegativity to
D) less electronegative than
E) more soluble than
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-17

7
18) How many lone pairs of electrons does the oxygen in a carbonyl group have? 18)
A) None, they're all bonded.
B) one
C) two
D) three
E) four
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-18

19) In the IUPAC naming system, a ketone is named by replacing the -e in the corresponding alkane 19)
name with
A) one. B) ene. C) al. D) yne. E) ol.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-19

20) In the IUPAC naming system, an aldehyde is named by replacing the -e of the name of the 20)
corresponding alkane with
A) yne. B) ene. C) one. D) al. E) ol.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-20

8
21) What is the name of this compound? 21)

A) 3-methyl-2-butanone
B) pentanone
C) 2-methylbutanone
D) 2-methyl-3-butanone
E) 3-methylbutanone
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-21

22) Formalin is 22)

A) a 40% aqueous solution of formaldehyde.
B) a polymer.
C) another name for formaldehyde.
D) a plastic.
E) an excellent solvent.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-22

9
23) Acetone is a ketone commonly used as a 23)
A) drain cleaner.
B) preservative.
C) solvent.
D) flavoring agent.
E) fuel.
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-23

24) The flavoring agent found in vanilla is 24)

A) a ketone.
B) an ester.
C) a thiol.
D) a hydrocarbon.
E) an aldehyde.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-24

10
25) What is the IUPAC name of this compound? 25)

A) 3-methylbutanone
B) 2-methylbutanone
C) 2-methyl-1-butanal
D) pentanone
E) 3-methylbutanal
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-25

26) What is the common name of this compound? 26)

A) ethyl methyl ketone

B) dimethyl ketone
C) diethyl ketone
D) acetone
E) 3-pentanone
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-26

11
27) Aldehydes have higher boiling points than alkanes of similar molar mass because of 27)
A) oxygen bonding.
B) ionic bonding.
C) covalent bonding.
D) hydrogen bonding.
E) dipole-dipole interactions.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-27

28) The increased boiling point of ketones compared to alkanes and ethers of similar molar mass is 28)
due to
A) hydrogen bonding.
B) resonance.
C) ionic interactions.
D) dipole-dipole interactions.
E) a bent chain structure.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-28

29) Low-molecular-weight ketones are soluble in water. What is the shortest length of the carbon 29)
chain where insolubility becomes important?
A) one B) two C) four D) five E) eight
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-29

12
30) Which of the following would NOT be water soluble? 30)
A) 3-heptanone
B) 2-butanone
C) propanal
D) acetone
E) formaldehyde
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-30

31) Which of the following ketones is the most soluble in water? 31)
A) O

CH3 - C - CH2 - CH2 - CH3

B) O

CH3 - CH - C - CH3
|
CH3
C) O

CH3 - CH2 - C - CH2 - CH3

D) O

CH3 - CH2 - C - CH2 - CH2 - CH3

E) O

CH3 C CH3
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-31

13
32) The reduction of 3-pentanone with hydrogen in the presence of a nickel catalyst will yield 32)
A) 3-pentanol.
B) diethyl alcohol.
C) pentane.
D) pentanaldehyde.
E) 2-pentene.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-32

33) The addition of hydrogen to an organic compound or the loss of oxygen is called 33)
A) dehydration.
B) oxidation.
C) hydration.
D) reduction.
E) halogenation.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-33

34) The hydrogenation of 2-methylpropanal yields 34)

A) 2-methylpropanoic acid.
B) 2-methyl-1-propanol.
C) 2-methyl-2-propanol.
D) 1-butanol.
E) 2-methyl-3-propanol.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-34

14
35) The Tollens' test may be used to distinguish 35)
A) aldehydes from ketones.
B) ketones from alcohols.
C) esters from acids.
D) acids from amines.
E) alcohols from alkenes.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-35

36) The Benedict's test may be used to distinguish 36)

A) alcohols from alkenes.
B) aldehydes from ketones.
C) ketones from alcohols.
D) acids from amines.
E) esters from acids.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-36

37) Aldehydes and ketones may be reduced to 37)

A) alcohols. B) esters. C) acids. D) ethers. E) alkanes.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-37

15
38) Which of the compounds would give a positive Tollens' test? 38)
A)

B)

C)

D)

E)

Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-38

39) An acetal is formed from two molecules of an alcohol and a(n) 39)
A) ester.
B) ether.
C) aldehyde.
D) carboxylic acid.
E) alkyl ether.
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-39

16
40) How many moles of an alcohol are needed to react with 1 mole of an aldehyde to form a 40)
hemiacetal?
A) 1.5 moles B) 1 moles C) 3.5 moles D) 3 moles E) 2 moles
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-40

41) How do sugars form cyclic hemiacetals? 41)

A) Two molecules of a sugar react with one another.
B) Functional groups within molecule of sugar react with each other.
C) A molecule of sugar reacts with an added alcohol.
D) A molecule of sugar reacts with an added aldehyde.
E) A sugar molecule decomposes.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-41

42) The product of adding two molecules of an alcohol to one molecule of an aldehyde in the 42)
presence of acid is a(n)
A) ether.
B) hemiacetal.
C) hydroxyl group.
D) acetal.
E) hemiether.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-42

17
43) Which of these compounds is the hemiacetal that forms when ethanol reacts with propanal? 43)
A) OH
|
CH3 - C - O - CH2 - CH3
|
H

B) OH
|
CH3 - CH2 - C - O - CH2 - CH3
|
H

C) O - CH2 - CH3
|
CH3 - CH2 - C - O - CH2 - CH3
|
H

D) O - CH2 - CH2 - CH3

|
CH3 - C - O - CH2 - CH2 - CH3
|
CH2 - CH2 - CH3
E) O - CH2 - CH3
|
CH3 - C - O - CH3
|
H

Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-43

44) What is the acetal formed when propanone reacts with two molecules of methanol? 44)
A) O - CH3
|
CH3 - C - CH3
|
O - CH3

18
 B) O - CH3
|
CH3 - C-O - CH3
|
O - CH3

C) OH
|
CH3 - C - CH3
|
CH3

D) CH3 CH3
| |
CH3 - C - O - C - CH3
| |
H H

E) OH
|
CH3 - C - CH3
|
O - CH3

Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 14.1-44

TRUE/FALSE. Write 'T' if the statement is true and 'F' if the statement is false.

45) All aldehydes have a carbonyl carbon bonded to at least two hydrogens. 45)
Answer: True False
Explanation:
ID: chem6tl 14.2-1

46) Many odors from solvents, paint removers, and perfumes are derived from aldehydes or ketones. 46)
Answer: True False
Explanation:
ID: chem6tl 14.2-2

19
47) In a ketone, the carbonyl group is bonded to two other carbon atoms. 47)
Answer: True False
Explanation:
ID: chem6tl 14.2-3

48) The carbonyl group consists of a carbon-oxygen single bond, and a second bond to hydrogen. 48)
Answer: True False
Explanation:
ID: chem6tl 14.2-4

49) The carbonyl group does not have a dipole. 49)

Answer: True False
Explanation:
ID: chem6tl 14.2-5

50) The suffix -one indicates an aldehyde in the IUPAC system of naming. 50)
Answer: True False
Explanation:
ID: chem6tl 14.2-6

51) The suffix -al indicates an aldehyde in the IUPAC system of naming. 51)
Answer: True False
Explanation:
ID: chem6tl 14.2-7

52) Acetone is a three-carbon aldehyde. 52)

Answer: True False
Explanation:
ID: chem6tl 14.2-8

53) Acetone is sometimes produced in pathological conditions such as diabetes. 53)

Answer: True False
Explanation:
ID: chem6tl 14.2-9

54) Formaldehyde is used in aqueous solution as a germicide and preservative. 54)

Answer: True False
Explanation:
ID: chem6tl 14.2-10

20
55) Excessive exposure to formaldehyde can irritate the eyes and respiratory tract. 55)
Answer: True False
Explanation:
ID: chem6tl 14.2-11

56) A major flavor component of vanilla is an aldehyde. 56)

Answer: True False
Explanation:
ID: chem6tl 14.2-12

57) The IUPAC name of this compound is 3-butanone. 57)

Answer: True False

Explanation:
ID: chem6tl 14.2-13

58) The common name of this compound is ethyl methyl ketone. 58)

Answer: True False

Explanation:
ID: chem6tl 14.2-14

59) The carbonyl group gives aldehydes higher boiling points than alkanes of similar molar mass. 59)
Answer: True False
Explanation:
ID: chem6tl 14.2-15

60) The carbonyl group gives ketones lower boiling points than alkanes of similar molar mass. 60)
Answer: True False
Explanation:
ID: chem6tl 14.2-16

61) Carbonyl compounds having fewer than four carbon atoms are very water soluble. 61)
Answer: True False
Explanation:
ID: chem6tl 14.2-17

21
62) Hexanal would be soluble in water. 62)
Answer: True False
Explanation:
ID: chem6tl 14.2-18

63) Propanal is more soluble in water than pentanal. 63)

Answer: True False
Explanation:
ID: chem6tl 14.2-19

64) Acetone would give a positive Tollens' test. 64)

Answer: True False
Explanation:
ID: chem6tl 14.2-20

65) The Tollens' test is used to distinguish between aldehydes and ketones. 65)
Answer: True False
Explanation:
ID: chem6tl 14.2-21

66) Ketones are oxidized to carboxylic acids. 66)

Answer: True False
Explanation:
ID: chem6tl 14.2-22

67) Ketones are reduced to secondary alcohols. 67)

Answer: True False
Explanation:
ID: chem6tl 14.2-23

68) Benedict's test can be used to determine if an aldehyde functional group is present. 68)
Answer: True False
Explanation:
ID: chem6tl 14.2-24

69) An acetal is formed from one molecule of an aldehyde or ketone and one molecule of alcohol. 69)
Answer: True False
Explanation:
ID: chem6tl 14.2-25

22
 70) A hemiacetal has alkoxy and hydroxyl functional groups bonded to the same carbon. 70)
Answer: True False
Explanation:
ID: chem6tl 14.2-26

71) Glucose forms a cyclic hemiacetal. 71)

Answer: True False
Explanation:
ID: chem6tl 14.2-27

72) This compound is an acetal. 72)

Answer: True False

Explanation:
ID: chem6tl 14.2-28

MATCHING. Choose the item in column 2 that best matches each item in column 1.
Select the correct name for the following.

73) O A) propanal 73)

CH3 -CH2 - C- CH2 -CH3
B) 1-propanone
Answer: C
ID: chem6tl 14.3-1
C) diethyl ketone

74) O 74)
D) 3-propanone
CH3 -CH2 -C-H
Answer: A
ID: chem6tl 14.3-2

23
Match the structural formula with the correct functional group.

75) O A) ether 75)

CH3 -C-H
B) ketone
Answer: C
ID: chem6tl 14.3-3
C) aldehyde

76) O 76)
CH3 - C- CH2 -CH3
Answer: B
ID: chem6tl 14.3-4

77) CH3 -CH2 -O- CH3 77)

Answer: A
ID: chem6tl 14.3-5

78) O 78)
CH3 -CH2 - C- H
Answer: C
ID: chem6tl 14.3-6

Identify the product, if any, that would form in each of the following reactions.

79) O A) CH3 -CH2 -CH3 79)

[O]
CH3 - C- H B) O
Answer: B
ID: chem6tl 14.3-7 CH3 -C- OH

80) O C) OH
80)
|
Ni CH3 -CH-CH3
CH3 -C-CH3 + H2

Answer: C
D) CH3 -CH3
ID: chem6tl 14.3-8

81) O
E) CH3 -CH2 -OH
81)
Ni
CH3 -C-H + H2

Answer: E
ID: chem6tl 14.3-9

24
Answer Key
Testname: UNTITLED2

1) B
Diff: 0

2) E
Diff: 0

3) B
Diff: 0

4) C
Diff: 0

5) B
Diff: 0

6) D
Diff: 0

7) B
Diff: 0

8) C
Diff: 0

9) D
Diff: 0

10) C
Diff: 0

11) B
Diff: 0

12) B
Diff: 0

13) A
Diff: 0

14) A
Diff: 0

15) A
Diff: 0

16) C
Diff: 0

17) A
Diff: 0

18) C
Diff: 0

19) A
Diff: 0

20) D
Diff: 0

21) A
Diff: 0

25
Answer Key
Testname: UNTITLED2

22) A
Diff: 0

23) C
Diff: 0

24) E
Diff: 0

25) E
Diff: 0

26) C
Diff: 0

27) E
Diff: 0

28) D
Diff: 0

29) D
Diff: 0

30) A
Diff: 0

31) E
Diff: 0

32) A
Diff: 0

33) D
Diff: 0

34) B
Diff: 0

35) A
Diff: 0

36) B
Diff: 0

37) A
Diff: 0

38) A
Diff: 0

39) C
Diff: 0

40) B
Diff: 0

41) B
Diff: 0

42) D
Diff: 0

26
Answer Key
Testname: UNTITLED2

43) B
Diff: 0

44) A
Diff: 0

45) FALSE
Diff: 0

46) TRUE
Diff: 0

47) TRUE
Diff: 0

48) FALSE
Diff: 0

49) FALSE
Diff: 0

50) FALSE
Diff: 0

51) TRUE
Diff: 0

52) FALSE
Diff: 0

53) TRUE
Diff: 0

54) TRUE
Diff: 0

55) TRUE
Diff: 0

56) TRUE
Diff: 0

57) FALSE
Diff: 0

58) TRUE
Diff: 0

59) TRUE
Diff: 0

60) FALSE
Diff: 0

61) TRUE
Diff: 0

62) FALSE
Diff: 0

63) TRUE
Diff: 0

27
Answer Key
Testname: UNTITLED2

64) FALSE
Diff: 0

65) TRUE
Diff: 0

66) FALSE
Diff: 0

67) TRUE
Diff: 0

68) TRUE
Diff: 0

69) FALSE
Diff: 0

70) TRUE
Diff: 0

71) TRUE
Diff: 0

72) TRUE
Diff: 0

73) C
Diff: 0

74) A
Diff: 0

75) C
Diff: 0

76) B
Diff: 0

77) A
Diff: 0

78) C
Diff: 0

79) B
Diff: 0

80) C
Diff: 0

81) E
Diff: 0

28