77. What is the common name for the following compound?

A. hexyl ether
B. propyl isopropyl ether
C. isopropyl propyl ether
D. none of these

78. What is the approximate C-O-C bond angle in the cyclic ether ethylene oxide, C2H4O?
A. 60
B. 90
C. 109
D. 120

79. Which of the following explains why the boiling points of ethers are more similar to those of comparable
alkanes than to those of comparable alcohols?
A. both ether molecules and alkane molecules are nonpolar
B. hydrogen bonding between ether molecules is weak
C. although ether molecules are polar they cannot form hydrogen bonds to other ether molecules
D. none of the above

80. Which of the following correctly gives the order of boiling points for the molecules propane, dimethyl ether,
and ethanol?
A. ethanol > dimethyl ether > propane
B. ethanol > propane > dimethyl ether
C. propane > dimethyl ether > ethanol
D. propane > ethanol > dimethyl ether

81. Which of the following correctly gives the order of boiling points for the molecules hexane, pentanol, and
ethoxypropane?
A. hexane > ethoxypropane > pentanol
B. hexane > pentanol > ethoxypropane
C. pentanol > ethoxypropane > hexane
D. pentanol > hexane > ethoxypropane

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 82. Which of the following correctly gives the order of boiling points for the molecules pentanol, ethyl propyl
ether, and hexane?
A. hexane < ethyl propyl ether < pentanol
B. hexane < pentanol < ethyl propyl ether
C. pentanol < ethyl propyl ether < hexane
D. pentanol < hexane < ethyl propyl ether

83. Ethers react readily with which of the following?

A. H2
B. most acids
C. potassium dichromate
D. none of these

84. Which of the following is true of liquid ethers?

A. they are both volatile and highly flammable
B. they are neither volatile nor highly flammable
C. they are volatile, but are not flammable
D. they are flammable, but are not volatile

85. Which of the following ethers was frequently used in the past as an anesthetic?
A. diethyl ether
B. dimethyl ether
C. ethyl methyl ether
D. ethyl propyl ether

86. Which of the following is used today as an inhalation anesthetic??

A.

B.
C. both (a) and (b)
D. neither (a) nor (b)

87. Negative side effects of the use of diethyl ether as an anesthetic include which of the following?
A. greatly reduced blood pressure
B. highly increased pulse rate
C. irritation of the respiratory passages
D. all of these

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 88. Two commonly used inhalation anesthetics are Ethrane and Forane. They are two of many isomeric ethers
which have the molecular formula C3H2ClF5O. In how many of these isomeric ethers are three F atoms bonded
to a single carbon atom?
A. 6
B. 8
C. 10
D. 12

89. Thiols are most closely related to which of the following classes of compounds?
A. alcohols
B. aldehydes
C. carboxylic acids
D. ketones

90. Which of the following is the IUPAC name for ?

A. isobutyl mercaptan
B. sec-butyl mercaptan
C. 2-methyl-1-propanthiol
D. 2-methyl-1-propanethiol

91. Which of the following is the common name for ?

A. isobutyl mercaptan
B. sec-butyl mercaptan
C. 2-methyl-1-propanthiol
D. 2-methyl-1-propanethiol

92. Which of the following is the IUPAC name for ?

A. isobutyl mercaptan
B. sec-butyl mercaptan
C. 2-butanethiol
D. 1-methyl-1-propanethiol

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 93. Which of the following is the common name for ?
A. isobutyl mercaptan
B. sec-butyl mercaptan
C. 2-methyl-1-propanthiol
D. 2-methyl-1-propanethiol

94. What is the IUPAC name of isobutyl mercaptan?

A. 2-butanethiol
B. 2-methyl-1-propanethiol
C. 2-methyl-2-propanethiol
D. none of these

95. What is the IUPAC name of sec-butyl mercaptan?

A. 2-butanethiol
B. 2-methyl-1-propanethiol
C. 2-methyl-2-propanethiol
D. none of these

96. What is the IUPAC name of tert-butyl mercaptan?

A. 2-butanethiol
B. 2-methyl-1-propanethiol
C. 2-methyl-2-propanethiol
D. none of these

97. What is the approximate pKa of a thiol?

A. 5
B. 7
C. 10
D. 14

98. Which of the following explains the fact that there is extensive hydrogen bonding in alcohols but little if any
in thiols?
A. thiols are much more acidic than alcohols
B. sulfur is less electronegative than oxygen
C. both (a) and (b)
D. neither (a) nor (b)

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 99. Which of the following statements are true?
(i) 1-propanethiol has a higher boiling point than 1-propanol
(ii) 1-propanethiol has a comparable boiling point to CH3CH2SCH3 (ethyl methyl sulfide)
(iii) 1-propanethiol is much more acidic than 1-propanol.
A. (i) and (ii) only
B. (i) and (iii) only
C. (ii) and (iii) only
D. (i), (ii) and (iii)

100. Which of the following is an important biological reaction of thiols?

A. the combination of two thiols and the elimination of H2S to yield a thioether
B. the reduction of two thiols to form a disulfide
C. the oxidation of two thiols to form a disulfide
D. none of the above

101. Which of the following is true of the relationship between thiols and disulfides?
A. thiols are easily oxidized to disulfides, and disulfides are easily reduced to thiols
B. thiols are not easily oxidized to disulfides, and disulfides are not easily reduced to thiols
C. thiols are easily oxidized to disulfides, but disulfides are not easily reduced to thiols
D. thiols are not easily oxidized to disulfides, but disulfides are easily reduced to thiols

102. Which of the following statements are true?

(i) the pKa of thiols is similar to that to phenols
(ii) little or no hydrogen bonding occurs between thiol molecules
(iii) thiols and disulfides are important in nucleic acid chemistry
A. (i) and (ii) only
B. (i) and (iii) only
C. (ii) and (iii) only
D. (i), (ii) and (iii)

103. The conversion of coal or methane to formaldehyde involves which of the following sequences of
reactions?
A. three successive oxidations
B. three successive reductions
C. reduction, oxidation, reduction
D. oxidation, reduction, oxidation

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 104. Which of the following alcohols is used as an oxygenate additive in gasoline used by conventional road
vehicles?
A. ethanol
B. isopropanol
C. methanol
D. none of these

105. Which of the following is an important intermediate in the production of ethylene glycol?
A. diethyl ether
B. ethanol
C. ethylene oxide
D. none of these

106. In addition to its use as an automobile antifreeze, how else is ethylene glycol used?
A. as a component of various inks
B. as a solvent for paints
C. as a starting material in the manufacture of the polymer PET
D. all of the above

107. Rubbing alcohol is made from which of the following precursors?

A. ethanol
B. propene
C. 2-methylpropane
D. none of these

108. Which of the following can be obtained using propene as a starting material?
A. glycerin
B. isopropyl alcohol
C. epichlorohydrin
D. all of these

109. Which of the following is the major source of glycerin used for industrial and commercial purposes?
A. as a byproduct in the manufacture of soaps
B. a multi-step oxidation process from propene
C. the one step oxidation of methanol
D. none of the above

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