Deck 13: Alcohols, Phenols, Thiols, and Ethers
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Deck 13: Alcohols, Phenols, Thiols, and Ethers
1
Which one of the following compounds is an alcohol?
A)
B)
C)
D)
E)
A)

B)

C)

D)

E)


2
The common name for the compound
is
A)3-ether pentane.
B)3-pentanol.
C)3-hexanol.
D)ethyl propyl ketone.
E)ethyl propyl ether.

A)3-ether pentane.
B)3-pentanol.
C)3-hexanol.
D)ethyl propyl ketone.
E)ethyl propyl ether.
ethyl propyl ether.
3
Alcohols contain which functional group?
A)amide
B)amine
C)hydroxyl
D)thiol
A)amide
B)amine
C)hydroxyl
D)thiol
hydroxyl
4
What is the common name of this compound? 
A)propylcyclopentanol
B)cyclopentyl propyl ketone
C)3-cyclopentylpropanol
D)cyclopentyl propyl ether
E)1-cyclopropyl-1-propylalcohol

A)propylcyclopentanol
B)cyclopentyl propyl ketone
C)3-cyclopentylpropanol
D)cyclopentyl propyl ether
E)1-cyclopropyl-1-propylalcohol
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5
What is the IUPAC name for 
A)2-propanethiol
B)propyl thiol
C)2-butanethiol
D)1-propanethiol
E)1-butanethiol

A)2-propanethiol
B)propyl thiol
C)2-butanethiol
D)1-propanethiol
E)1-butanethiol
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6
Why has diethyl ether been replaced as a general anesthetic?
A)It is slightly polar.
B)It can hydrogen bond to water.
C)It is very volatile and highly flammable.
D)It is slightly soluble in water.
E)It is not very reactive.
A)It is slightly polar.
B)It can hydrogen bond to water.
C)It is very volatile and highly flammable.
D)It is slightly soluble in water.
E)It is not very reactive.
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7
Which one of the following compounds is a thiol?
A)
B)
C)
D)
E)
A)

B)

C)

D)

E)

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8
Which of the following does NOT involve methanol?
A)alcoholic beverages
B)paint remover
C)solvents
D)making plastics
E)racing fuel
A)alcoholic beverages
B)paint remover
C)solvents
D)making plastics
E)racing fuel
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9
What is the name for this compound?

A) cyclobenzenol
B) cyclohexanol
C) cyclopentanol
D) glycerol
E) phenol

A) cyclobenzenol
B) cyclohexanol
C) cyclopentanol
D) glycerol
E) phenol
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10
What is the IUPAC name for this compound?

A) 3-methyl-5-pentanol
B) 3-methylpentanol
C) 3-methyl-1-pentanol
D) 3-methyl-6-hexanol
E) 3-methyl-1-hexanol

A) 3-methyl-5-pentanol
B) 3-methylpentanol
C) 3-methyl-1-pentanol
D) 3-methyl-6-hexanol
E) 3-methyl-1-hexanol
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11
Thiols are strong-smelling compounds responsible for
A)salty odors.
B)flowery odors.
C)fruity odors.
D)sharp odors.
E)skunky or bad-smelling odors.
A)salty odors.
B)flowery odors.
C)fruity odors.
D)sharp odors.
E)skunky or bad-smelling odors.
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12
Which of the following is the IUPAC name for the compound below? 
A)2-methyl-3-heptanol
B)5-methyl-4-hexanol
C)5-methyl-4-pentanol
D)2-methyl-3-hexanol
E)2-methyl-3-pentanol

A)2-methyl-3-heptanol
B)5-methyl-4-hexanol
C)5-methyl-4-pentanol
D)2-methyl-3-hexanol
E)2-methyl-3-pentanol
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13
The condensed structural formula for 2,3-dichloro-4-methylcyclohexanol is
A)
B)
C)
D)
E)
A)

B)

C)

D)

E)

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14
1,2-ethanediol (ethylene glycol)has uses that include
A)production of synthetic fibers.
B)solvent for paint.
C)solvent for ink.
D)antifreeze.
E)All of the above.
A)production of synthetic fibers.
B)solvent for paint.
C)solvent for ink.
D)antifreeze.
E)All of the above.
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15
What is the IUPAC name of this compound? 
A)2-propanol
B)2-methyl-2-propanol
C)butanol
D)propanol
E)2-methylbutanol

A)2-propanol
B)2-methyl-2-propanol
C)butanol
D)propanol
E)2-methylbutanol
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16
What is the name for this compound? 
A)4-bromo-1-ethyl-5-phenol
B)6-bromo-3-ethylphenol
C)2-bromo-5-methylphenol
D)2-bromo-5-ethylcyclohexanol
E)2-bromo-5-ethylphenol

A)4-bromo-1-ethyl-5-phenol
B)6-bromo-3-ethylphenol
C)2-bromo-5-methylphenol
D)2-bromo-5-ethylcyclohexanol
E)2-bromo-5-ethylphenol
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17
The compound
is in the organic family known as
A) ethers.
B) sulfides.
C) amino acids.
D) alcohols.
E) thiols.

A) ethers.
B) sulfides.
C) amino acids.
D) alcohols.
E) thiols.
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18
The common name of CH3-CH2-O-CH2-CH3 is
A)butyl ether.
B)dimethyl ether.
C)dibutyl ether.
D)diethyl ether.
E)2-etherbutane.
A)butyl ether.
B)dimethyl ether.
C)dibutyl ether.
D)diethyl ether.
E)2-etherbutane.
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19
A phenol has an -OH group bonded to a(n)
A)disubstituted carbon.
B)singly substituted or unsubstituted carbon.
C)tetrasubstituted carbon.
D)aromatic carbon.
E)trisubstituted carbon.
A)disubstituted carbon.
B)singly substituted or unsubstituted carbon.
C)tetrasubstituted carbon.
D)aromatic carbon.
E)trisubstituted carbon.
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20
Thiols have structures similar to alcohols except that they contain
A)more than one carbon.
B)nitrogen in place of oxygen in the functional group.
C)sulfur in place of oxygen in the functional group.
D)lithium in place of oxygen in the functional group.
E)three alcohol groups.
A)more than one carbon.
B)nitrogen in place of oxygen in the functional group.
C)sulfur in place of oxygen in the functional group.
D)lithium in place of oxygen in the functional group.
E)three alcohol groups.
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21
What type of alcohol is resistant to oxidation?
A)primary
B)secondary
C)tertiary
D)quaternary
E)none
A)primary
B)secondary
C)tertiary
D)quaternary
E)none
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22
In a tertiary alcohol, how many alkyl groups are attached to the carbon atom bonded to the -OH group?
A)none
B)one
C)two
D)three
E)four
A)none
B)one
C)two
D)three
E)four
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23
A secondary alcohol has a hydroxyl group bonded to a(n)
A)carbon that is bonded to two alkyl groups.
B)aromatic carbon.
C)carbon that is bonded to one alkyl group.
D)carbon that is bonded to three alkyl groups.
A)carbon that is bonded to two alkyl groups.
B)aromatic carbon.
C)carbon that is bonded to one alkyl group.
D)carbon that is bonded to three alkyl groups.
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24
The dehydration product of
in the presence of acid is
A) cyclopropene.
B) propene.
C) cyclopropane.
D)
E) propyne.

A) cyclopropene.
B) propene.
C) cyclopropane.
D)

E) propyne.
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25
Which of the following compounds is a secondary alcohol?
A)
B)
C)
D)
E)
A)

B)

C)

D)

E)

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26
What is the product when this compound undergoes oxidation? 
A)3,3-dimethylbutanal
B)hexanal
C)2,2-dimethylbutanal
D)3,3-dimethyl-1-butanone
E)2,2-dimethyl-4-butanone

A)3,3-dimethylbutanal
B)hexanal
C)2,2-dimethylbutanal
D)3,3-dimethyl-1-butanone
E)2,2-dimethyl-4-butanone
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27
A tertiary alcohol has a hydroxyl group bonded to a
A)carbon that is bonded to three alkyl groups.
B)double bonded carbon.
C)carbon that is bonded to one alkyl group.
D)triple-bonded carbon.
E)carbon that is bonded to two alkyl groups.
A)carbon that is bonded to three alkyl groups.
B)double bonded carbon.
C)carbon that is bonded to one alkyl group.
D)triple-bonded carbon.
E)carbon that is bonded to two alkyl groups.
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28
The IUPAC name for the compound CH3-CH2-CH2-O-CH2-CH3 is
A)2-ethoxyethane.
B)1-propoxyethane.
C)ethyl propyl ether.
D)1-ethoxypropane.
E)2-ethoxypropane.
A)2-ethoxyethane.
B)1-propoxyethane.
C)ethyl propyl ether.
D)1-ethoxypropane.
E)2-ethoxypropane.
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29
What is the product when the following compound is oxidized? 
A)an aldehyde
B)an ether
C)an alkane
D)an alkene
E)a ketone

A)an aldehyde
B)an ether
C)an alkane
D)an alkene
E)a ketone
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30
Which of the following compounds is a weak acid?
A)cyclohexanol
B)phenol
C)ethanal
D)ethanol
E)acetone
A)cyclohexanol
B)phenol
C)ethanal
D)ethanol
E)acetone
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31
The alcohol in this list that would be most soluble in water is
A)1-heptanol.
B)ethanol.
C)1-butanol.
D)1-pentanol.
E)1-hexanol.
A)1-heptanol.
B)ethanol.
C)1-butanol.
D)1-pentanol.
E)1-hexanol.
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32
Tertiary alcohols cannot be oxidized because
A)the alcohol carbon is bonded to four groups so no hydrogen can be added to it.
B)the alcohol carbon is bonded to four groups so no oxygen can be added to it.
C)there are no oxygen atoms to remove from the alcohol carbon.
D)there are no hydrogen atoms attached to the alcohol carbon.
E)the alcohol carbon is too electronegative to have hydrogen removed from it.
A)the alcohol carbon is bonded to four groups so no hydrogen can be added to it.
B)the alcohol carbon is bonded to four groups so no oxygen can be added to it.
C)there are no oxygen atoms to remove from the alcohol carbon.
D)there are no hydrogen atoms attached to the alcohol carbon.
E)the alcohol carbon is too electronegative to have hydrogen removed from it.
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33
What kind of bonds do alcohols form between individual molecules?
A)carbon bonds
B)hydrogen bonds
C)oxygen bonds
D)single bonds
E)ionic bonds
A)carbon bonds
B)hydrogen bonds
C)oxygen bonds
D)single bonds
E)ionic bonds
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34
What is the common name of the ether that is an isomer of 2-propanol?
A)isopropyl ether
B)ethyl methyl ether
C)1-propanol
D)dimethyl ether
E)diethyl ether
A)isopropyl ether
B)ethyl methyl ether
C)1-propanol
D)dimethyl ether
E)diethyl ether
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35
A primary alcohol has a hydroxyl group bonded to a(n)
A)aromatic carbon.
B)carbon that is bonded to one alkyl group.
C)carbon that is bonded to two alkyl groups.
D)carbon that is bonded to three alkyl groups.
A)aromatic carbon.
B)carbon that is bonded to one alkyl group.
C)carbon that is bonded to two alkyl groups.
D)carbon that is bonded to three alkyl groups.
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36
What type of alcohol undergoes oxidation to yield a ketone?
A)primary alcohol
B)secondary alcohol
C)both primary and secondary alcohols
D)all classes of alcohols
E)both secondary and tertiary alcohols
A)primary alcohol
B)secondary alcohol
C)both primary and secondary alcohols
D)all classes of alcohols
E)both secondary and tertiary alcohols
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37
What is the common name of the ether that is an isomer of 1-butanol?
A)butyl ether
B)dimethyl ether
C)isopropyl ether
D)diethyl ether
E)ethyl methyl ether
A)butyl ether
B)dimethyl ether
C)isopropyl ether
D)diethyl ether
E)ethyl methyl ether
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38
The dehydration of an alcohol in the presence of a strong acid yields
A)an alkane.
B)a ketone.
C)an alkene.
D)an alcohol.
E)an aldehyde.
A)an alkane.
B)a ketone.
C)an alkene.
D)an alcohol.
E)an aldehyde.
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39
When 2-methyl-2-butanol undergoes dehydration in acid, the major product is
A)2-methylbutanal.
B)2-methyl-2-butene.
C)2-methylbutanone.
D)2-pentanone.
E)hexene.
A)2-methylbutanal.
B)2-methyl-2-butene.
C)2-methylbutanone.
D)2-pentanone.
E)hexene.
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40
In the oxidation of an alcohol to a ketone, there is
A)a loss of carbon.
B)a loss of hydrogen.
C)a gain of oxygen.
D)a loss of oxygen.
E)a gain of hydrogen.
A)a loss of carbon.
B)a loss of hydrogen.
C)a gain of oxygen.
D)a loss of oxygen.
E)a gain of hydrogen.
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41
Which compound will undergo oxidation to yield the following?

A)pentanol
B)methylcyclobutanol
C)cyclopentene
D)cyclopentanol
E)cyclopentane

A)pentanol
B)methylcyclobutanol
C)cyclopentene
D)cyclopentanol
E)cyclopentane
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42
Alcohols undergo combustion to form
A)aldehydes.
B)alkenes.
C)water, carbon dioxide, and energy.
D)ethers.
E)ketones.
A)aldehydes.
B)alkenes.
C)water, carbon dioxide, and energy.
D)ethers.
E)ketones.
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43
The dehydration product of
in the presence of acid is
A)
B) propene.
C) cyclopropane.
D) cyclopropene.
E) propyne.

A)

B) propene.
C) cyclopropane.
D) cyclopropene.
E) propyne.
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44
In the dehydration of an alcohol to an alkene, what is produced in addition to the alkene?
A)carbon monoxide
B)hydrogen
C)water
D)oxygen
E)carbon dioxide
A)carbon monoxide
B)hydrogen
C)water
D)oxygen
E)carbon dioxide
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45
When a primary alcohol is completely oxidized, the product is
A)a carboxylic acid.
B)a ketone.
C)an alkane.
D)an aldehyde.
E)another alcohol.
A)a carboxylic acid.
B)a ketone.
C)an alkane.
D)an aldehyde.
E)another alcohol.
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46
Secondary alcohols are oxidized to
A)ketones.
B)esters.
C)ethers.
D)carboxylic acids.
E)aldehydes.
A)ketones.
B)esters.
C)ethers.
D)carboxylic acids.
E)aldehydes.
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47
Methanol is toxic because it is ________ by the liver to carboxylic acids.
A)conjugated
B)oxidized
C)protonated
D)hydrated
E)reduced
A)conjugated
B)oxidized
C)protonated
D)hydrated
E)reduced
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48
Thiols can be oxidized to
A)carboxylic acids.
B)disulfides.
C)ketones.
D)thioethers.
E)aldehydes.
A)carboxylic acids.
B)disulfides.
C)ketones.
D)thioethers.
E)aldehydes.
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49
Tertiary alcohols are oxidized to
A)carboxylic acids.
B)secondary alcohols.
C)aldehydes.
D)ketones.
E)Tertiary alcohols do not undergo oxidation.
A)carboxylic acids.
B)secondary alcohols.
C)aldehydes.
D)ketones.
E)Tertiary alcohols do not undergo oxidation.
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