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 alcohol? 1)

A) CH3 - CH = CH - CH2 - CH3
B) CH3 - CH2 - O - CH2 - CH3
C) OH
|
CH3 - CH - CH3
D) O

CH3 - CH2 - CH
E) CH3 - SH
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-1

2) The compound CH3 - CH2 - SH is in the organic family known as 2)

A) sulfides.
B) ethers.
C) thiols.
D) alcohols.
E) amino acids.
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-2

1
3) Alcohols contain which functional group? 3)
A) hydroxyl B) thiol C) amide D) amine
Answer: A
Explanation: A)
B)
C)
D)
ID: chem6tl 13.1-3

4) What is the IUPAC name for this compound? 4)

A) 3-methyl-1-pentanol
B) 3-methyl-6-hexanol
C) 3-methyl-1-hexanol
D) 3-methylpentanol
E) 3-methyl-5-pentanol
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-4

2
5) Which of the following is the IUPAC name for the compound below? 5)

A) 2-methyl-3-hexanol
B) 2-methyl-3-pentanol
C) 2-methyl-3-heptanol
D) 5-methyl-4-hexanol
E) 5-methyl-4-pentanol
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-5

6) The condensed structural formula for 2,3-dichloro-4-methylcyclohexanol is 6)

A)

B)

C)

3
 D)

E)

Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-6

7) What is the IUPAC name of this compound? 7)

OH
|
CH3 - C - CH3
|
CH3

A) 2-propanol
B) 2-methylbutanol
C) 2-methyl-2-propanol
D) propanol
E) butanol
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-7

4
8) Which one of the following compounds is a thiol? 8)
A) CH3 - SH
B) CH3 - CH = CH - CH2 - CH3

C) OH
|
CH3 - CH - CH3

D) O

CH3 - CH2 - CH

E) CH3 - CH2 - O - CH2 - CH3

Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-8

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

A) 6-bromo-3-ethylphenol
B) 2-bromo-5-ethylcyclohexanol
C) 4-bromo-1-ethyl-5-phenol
D) 2-bromo-5-ethylphenol
E) 2-bromo-5-methylphenol
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-9

5
10) What is the name for this compound? 10)

A) cyclobenzenol
B) cyclohexanol
C) phenol
D) cyclopentanol
E) glycerol
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-10

11) A phenol has an -OH group bonded to a(n) 11)

A) trisubstituted carbon.
B) aromatic carbon.
C) singly substituted or unsubstituted carbon.
D) tetrasubstituted carbon.
E) disubstituted carbon.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-11

6
12) Thiols have structures similar to alcohols except that they contain 12)
A) lithium in place of oxygen in the functional group.
B) nitrogen in place of oxygen in the functional group.
C) more than one carbon.
D) three alcohol groups.
E) sulfur in place of oxygen in the functional group.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-12

13) Which of the following does NOT involve methanol? 13)

A) solvents
B) alcoholic beverages
C) making plastics
D) racing fuel
E) paint remover
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-13

14) 1,2-ethanediol (ethylene glycol) has uses that include 14)

A) solvent for ink.
B) antifreeze.
C) solvent for paint.
D) production of synthetic fibers.
E) All of the above.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-14

7
15) What is the IUPAC name for CH3 - CH2 - CH2 - SH? 15)
A) 1-butanethiol
B) 2-propanethiol
C) propyl thiol
D) 1-propanethiol
E) 2-butanethiol
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-15

16) Thiols are strong-smelling compounds responsible for 16)

A) flowery odors.
B) sharp odors.
C) salty odors.
D) skunky or bad-smelling odors.
E) fruity odors.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-16

8
17) What is the common name of this compound? 17)

A) propylcyclopentanol
B) cyclopentyl propyl ketone
C) 1-cyclopropyl-1-propylalcohol
D) 3-cyclopentylpropanol
E) cyclopentyl propyl ether
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-17

18) The common name for the compound CH3 - CH2 - CH2 - O - CH2 - CH3 is 18)
A) 3-ether pentane.
B) 3-hexanol.
C) ethyl propyl ketone.
D) 3-pentanol.
E) ethyl propyl ether.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-18

9
19) The common name of CH3 - CH2 - O - CH2 - CH3 is 19)
A) dibutyl ether.
B) diethyl ether.
C) 2-etherbutane.
D) dimethyl ether.
E) butyl ether.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-19

20) Why has diethyl ether been replaced as a general anesthetic? 20)
A) It is very volatile and highly flammable.
B) It is slightly soluble in water.
C) It can hydrogen bond to water.
D) It is not very reactive.
E) It is slightly polar.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-20

21) What is the common name of the ether that is an isomer of 2-propanol? 21)
A) diethyl ether
B) 1-propanol
C) isopropyl ether
D) ethyl methyl ether
E) dimethyl ether
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-21

10
22) What is the common name of the ether that is an isomer of 1-butanol? 22)
A) butyl ether
B) dimethyl ether
C) ethyl methyl ether
D) isopropyl ether
E) diethyl ether
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-22

23) The IUPAC name for the compound CH3 - CH2 - CH2 - O - CH2 - CH3 is 23)
A) 2-ethoxypropane.
B) 1-ethoxypropane.
C) ethyl propyl ether.
D) 2-ethoxyethane.
E) 1-propoxyethane.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-23

24) The alcohol in this list that would be most soluble in water is 24)
A) 1-hexanol.
B) 1-butanol.
C) 1-pentanol.
D) ethanol.
E) 1-heptanol.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-24

11
25) Which of the following compounds is a weak acid? 25)
A) ethanal
B) acetone
C) cyclohexanol
D) ethanol
E) phenol
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-25

26) Which of the following compounds is a secondary alcohol? 26)

A) CH3 - CH - O - CH3
|
CH3

B) CH3 - CH - OH
|
CH3
C) CH3 OH

D) CH3
|
CH3 - C - CH3
|
OH

E) OH
|
CH3 - CH2 - C - CH3
|
CH3

Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-26

12
27) In a tertiary alcohol, how many alkyl groups are attached to the carbon atom bonded to the -OH 27)
group?
A) none B) one C) two D) three E) four
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-27

28) A primary alcohol has a hydroxyl group bonded to a(n) 28)

A) carbon that is bonded to three alkyl groups.
B) aromatic carbon.
C) carbon that is bonded to one alkyl group.
D) carbon that is bonded to two alkyl groups.
Answer: C
Explanation: A)
B)
C)
D)
ID: chem6tl 13.1-28

29) A secondary alcohol has a hydroxyl group bonded to a(n) 29)

A) carbon that is bonded to two alkyl groups.
B) aromatic carbon.
C) carbon that is bonded to three alkyl groups.
D) carbon that is bonded to one alkyl group.
Answer: A
Explanation: A)
B)
C)
D)
ID: chem6tl 13.1-29

13
30) A tertiary alcohol has a hydroxyl group bonded to a 30)
A) triple-bonded carbon.
B) double bonded carbon.
C) carbon that is bonded to two alkyl groups.
D) carbon that is bonded to one alkyl group.
E) carbon that is bonded to three alkyl groups.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-30

31) What kind of bonds do alcohols form between individual molecules? 31)
A) oxygen bonds
B) carbon bonds
C) ionic bonds
D) single bonds
E) hydrogen bonds
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-31

32) The dehydration of an alcohol in the presence of a strong acid yields 32)
A) an alkene.
B) an alkane.
C) an alcohol.
D) an aldehyde.
E) a ketone.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-32

14
33) The dehydration product of CH3 - CH2 - CH2 - OH in the presence of acid is 33)
A) cyclopropene.
B) CH2 = C = CH2 .
C) cyclopropane.
D) propene.
E) propyne.
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-33

34) When 2-methyl-2-butanol undergoes dehydration in acid, the major product is 34)
A) 2-pentanone.
B) 2-methyl-2-butene.
C) 2-methylbutanal.
D) 2-methylbutanone.
E) hexene.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-34

35) In the oxidation of an alcohol to a ketone, there is 35)

A) a loss of oxygen.
B) a gain of oxygen.
C) a loss of hydrogen.
D) a gain of hydrogen.
E) a loss of carbon.
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-35

15
36) What is the product when this compound undergoes oxidation? 36)

CH3
|
CH3 - C - CH2 - CH2 - OH
|
CH3

A) 2,2-dimethyl-4-butanone
B) 3,3-dimethyl-1-butanone
C) 3,3-dimethylbutanal
D) hexanal
E) 2,2-dimethylbutanal
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-36

37) What type of alcohol undergoes oxidation to yield a ketone? 37)

A) secondary alcohol
B) both secondary and tertiary alcohols
C) primary alcohol
D) all classes of alcohols
E) both primary and secondary alcohols
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-37

16
38) Tertiary alcohols cannot be oxidized because 38)
A) there are no hydrogen atoms attached to the alcohol carbon.
B) the alcohol carbon is bonded to four groups so no hydrogen can be added to it.
C) there are no oxygen atoms to remove from the alcohol carbon.
D) the alcohol carbon is bonded to four groups so no oxygen can be added to it.
E) the alcohol carbon is too electronegative to have hydrogen removed from it.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-38

39) What type of alcohol is resistant to oxidation? 39)

A) primary
B) secondary
C) tertiary
D) quaternary
E) none
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-39

17
40) What is the product when the following compound is oxidized? 40)

A) a ketone
B) an alkene
C) an alkane
D) an ether
E) an aldehyde
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-40

41) Which compound will undergo oxidation to yield the following? 41)

A) methylcyclobutanol
B) pentanol
C) cyclopentanol
D) cyclopentene
E) cyclopentane
Answer: C
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-41

18
42) In the dehydration of an alcohol to an alkene, what is produced in addition to the alkene? 42)
A) carbon dioxide
B) carbon monoxide
C) hydrogen
D) water
E) oxygen
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-42

43) When a primary alcohol is completely oxidized, the product is 43)

A) a carboxylic acid.
B) another alcohol.
C) a ketone.
D) an alkane.
E) an aldehyde.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-43

44) Methanol is toxic because it is ________ by the liver to carboxylic acids. 44)
A) reduced
B) hydrated
C) conjugated
D) oxidized
E) protonated
Answer: D
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-44

19
45) Secondary alcohols are oxidized to 45)
A) ketones.
B) carboxylic acids.
C) esters.
D) ethers.
E) aldehydes.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-45

46) Tertiary alcohols are oxidized to 46)

A) secondary alcohols.
B) carboxylic acids.
C) aldehydes.
D) ketones.
E) Tertiary alcohols do not undergo oxidation.
Answer: E
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-46

47) Thiols can be oxidized to 47)

A) disulfides.
B) aldehydes.
C) thioethers.
D) ketones.
E) carboxylic acids.
Answer: A
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-47

20
 48) The dehydration product of OH in the presence of acid is 48)

CH3 - CH- CH3

A) cyclopropane.
B) propene.
C) CH 2 = C = CH2 .
D) cyclopropene.
E) propyne.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-48

49) Alcohols undergo combustion to form 49)

A) alkenes.
B) water, carbon dioxide, and energy.
C) ketones.
D) aldehydes.
E) ethers.
Answer: B
Explanation: A)
B)
C)
D)
E)
ID: chem6tl 13.1-49

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

50) Alcohols, ethers, and phenols contain oxygen bonded with only single bonds. 50)
Answer: True False
Explanation:
ID: chem6tl 13.2-1

51) Alcohols, ethers, and thiols contain oxygen atoms. 51)

Answer: True False
Explanation:
ID: chem6tl 13.2-2

21
52) Thiols usually have sweet odors. 52)
Answer: True False
Explanation:
ID: chem6tl 13.2-3

53) 1,2,3-propanetriol is obtained during the manufacture of soap. 53)

Answer: True False
Explanation:
ID: chem6tl 13.2-4

54) Glycerin strongly attracts and holds water, a property that makes it useful as a skin softener in 54)
cosmetics.
Answer: True False
Explanation:
ID: chem6tl 13.2-5

55) Diethyl ether has been replaced by halogenated anesthetics, which are less volatile and 55)
flammable.
Answer: True False
Explanation:
ID: chem6tl 13.2-6

56) Ethers can only be straight chain compounds. 56)

Answer: True False
Explanation:
ID: chem6tl 13.2-7

57) The following compound is ethyl propyl ether. 57)

Answer: True False

Explanation:
ID: chem6tl 13.2-8

58) The IUPAC name for ethyl propyl ether is 1-propoxyethane. 58)
Answer: True False
Explanation:
ID: chem6tl 13.2-9

22
59) Alcohols form hydrogen bonds; this accounts for their higher boiling points when compared to 59)
similar-sized alkanes.
Answer: True False
Explanation:
ID: chem6tl 13.2-10

60) The oxygen atom in alcohols decreases water solubility of the molecule. 60)
Answer: True False
Explanation:
ID: chem6tl 13.2-11

61) Phenols behave as weak acids in water. 61)

Answer: True False
Explanation:
ID: chem6tl 13.2-12

62) Alcohols can form hydrogen bonds. 62)

Answer: True False
Explanation:
ID: chem6tl 13.2-13

63) Heptanol is a water soluble alcohol. 63)

Answer: True False
Explanation:
ID: chem6tl 13.2-14

64) A secondary alcohol can be easily oxidized to a carboxylic acid. 64)

Answer: True False
Explanation:
ID: chem6tl 13.2-15

65) Cycloalkanols are straight chain alcohols. 65)

Answer: True False
Explanation:
ID: chem6tl 13.2-16

66) Alcohols can be dehydrated to form alkenes. 66)

Answer: True False
Explanation:
ID: chem6tl 13.2-17

23
 67) Primary alcohols can be oxidized to either aldehydes or ketones. 67)
Answer: True False
Explanation:
ID: chem6tl 13.2-18

68) Secondary alcohols can be oxidized to ketones. 68)

Answer: True False
Explanation:
ID: chem6tl 13.2-19

69) Tertiary alcohols are easily oxidized. 69)

Answer: True False
Explanation:
ID: chem6tl 13.2-20

70) Alcohols do not undergo combustion. 70)

Answer: True False
Explanation:
ID: chem6tl 13.2-21

MATCHING. Choose the item in column 2 that best matches each item in column 1.
Identify the product, if any, that would form in each of the following reactions.

[O] A) O
71) CH3 - CH2 - CH2 - OH 71)
Answer: A CH3 - CH2 - CH
ID: chem6tl 13.3-1

B) O
[O]
72) CH3 - CH2 - CH - OH 72)
| CH3 - CH2 - C - CH3
CH3
Answer: B
ID: chem6tl 13.3-2

24
Match the structural formula with the correct functional group.

73) CH3 - CH2 - OH A) ether 73)

Answer: B
ID: chem6tl 13.3-3 B) alcohol

74) CH3 - CH2 - O - CH3 C) thiol 74)

Answer: A
ID: chem6tl 13.3-4

75) CH3 - CH2 - SH 75)

Answer: C
ID: chem6tl 13.3-5

Select the correct name for the following.

76) CH3 - CH2 - CH2 - SH A) propane sulfide 76)

Answer: C
ID: chem6tl 13.3-6 B) 3-ethylphenol

77) CH3 - CH2 - O - CH2 - CH3 C) propanethiol 77)

Answer: E
ID: chem6tl 13.3-7 D) 1-ethyl-3- hydroxycyclohexene

78) E) diethyl ether 78)

Answer: B
ID: chem6tl 13.3-8

25
Classify the alcohols shown in column 1 as primary, secondary, or tertiary.

79) CH3 - CH2 - OH A) secondary 79)

Answer: B
ID: chem6tl 13.3-9 B) primary

80) CH3 C) tertiary 80)

|
CH3 - C - CH2 - OH
|
CH3

Answer: B
ID: chem6tl 13.3-10

81) OH 81)
|
CH3 - CH - CH3
Answer: A
ID: chem6tl 13.3-11

82) 82)

Answer: A
ID: chem6tl 13.3-12

83) CH3 83)

|
CH3 - C - CH2 - CH3
|
OH
Answer: C
ID: chem6tl 13.3-13

26
Answer Key
Testname: UNTITLED1

1) C
Diff: 0

2) C
Diff: 0

3) A
Diff: 0

4) A
Diff: 0

5) A
Diff: 0

6) C
Diff: 0

7) C
Diff: 0

8) A
Diff: 0

9) D
Diff: 0

10) C
Diff: 0

11) B
Diff: 0

12) E
Diff: 0

13) B
Diff: 0

14) E
Diff: 0

15) D
Diff: 0

16) D
Diff: 0

17) E
Diff: 0

18) E
Diff: 0

19) B
Diff: 0

20) A
Diff: 0

21) D
Diff: 0

27
Answer Key
Testname: UNTITLED1

22) E
Diff: 0

23) B
Diff: 0

24) D
Diff: 0

25) E
Diff: 0

26) B
Diff: 0

27) D
Diff: 0

28) C
Diff: 0

29) A
Diff: 0

30) E
Diff: 0

31) E
Diff: 0

32) A
Diff: 0

33) D
Diff: 0

34) B
Diff: 0

35) C
Diff: 0

36) C
Diff: 0

37) A
Diff: 0

38) A
Diff: 0

39) C
Diff: 0

40) A
Diff: 0

41) C
Diff: 0

42) D
Diff: 0

28
Answer Key
Testname: UNTITLED1

43) A
Diff: 0

44) D
Diff: 0

45) A
Diff: 0

46) E
Diff: 0

47) A
Diff: 0

48) B
Diff: 0

49) B
Diff: 0

50) TRUE
Diff: 0

51) FALSE
Diff: 0

52) FALSE
Diff: 0

53) TRUE
Diff: 0

54) TRUE
Diff: 0

55) TRUE
Diff: 0

56) FALSE
Diff: 0

57) TRUE
Diff: 0

58) FALSE
Diff: 0

59) TRUE
Diff: 0

60) FALSE
Diff: 0

61) TRUE
Diff: 0

62) TRUE
Diff: 0

63) FALSE
Diff: 0

29
Answer Key
Testname: UNTITLED1

64) FALSE
Diff: 0

65) FALSE
Diff: 0

66) TRUE
Diff: 0

67) FALSE
Diff: 0

68) TRUE
Diff: 0

69) FALSE
Diff: 0

70) FALSE
Diff: 0

71) A
Diff: 0

72) B
Diff: 0

73) B
Diff: 0

74) A
Diff: 0

75) C
Diff: 0

76) C
Diff: 0

77) E
Diff: 0

78) B
Diff: 0

79) B
Diff: 0

80) B
Diff: 0

81) A
Diff: 0

82) A
Diff: 0

83) C
Diff: 0

30