CHAPTER 14

Alcohols, Phenols, and Ethers

Test Bank

TYPE I MULTIPLE-CHOICE QUESTIONS

In each of the following multiple-choice questions, place the letter of the correct response in the blank
at the left. There is only one correct response for each question.

14.1 a The simplest alcohol, from a structural standpoint, contains how many carbon atoms
and how many oxygen atoms?
a) one carbon atom and one oxygen atom
b) one carbon atom and two oxygen atoms
c) two carbon atoms and one oxygen atom
d) two carbon atoms and two oxygen atoms

14.2 c The correct IUPAC name for CH3 CH OH is

CH3
a) isopropyl alcohol.
b) 2-methyl ethanol.
c) 2-propanol.
d) hydroxypropane.

14.3 d The correct IUPAC name for CH3 CH CH2 CH2 CH2 CH2 is
OH OH
a) hexyl dialcohol.
b) 2,6-dihydroxyhexane.
c) 2,6-hexanediol.
d) 1,5-hexanediol.

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Test Bank Chapter 14: Alcohols, Phenols, and Ethers 153

14.4 d [Algorithmic]Which of the following statements concerning common alcohols is

correct?
a) Wood alcohol and grain alcohol are one and the same.
b) Rubbing alcohol is pure isopropyl alcohol.
c) Absolute alcohol is pure methanol.
d) Denatured alcohol is drinking alcohol rendered unfit to drink.

14.5 b [Algorithmic]In which of the following pairs of alcohols do both members of the
pair contain two or more hydroxyl groups?
a) ethanol and ethylene glycol
b) ethylene glycol and glycerol
c) isopropyl alcohol and propylene glycol
d) t-butyl alcohol and s-butyl alcohol

14.6 c Alcohols have higher boiling points than alkanes of similar molecular mass because
a) alcohols are ionic compounds and alkanes are covalent compounds.
b) alkane molecules are polar and alcohol molecules are not.
c) hydrogen bonding occurs between alcohol molecules but not between alkane
molecules.
d) alcohols are acidic and alkanes are not.

14.7 c [Algorithmic]How many hydrogen bonds can form between an ethanol molecule
and other ethanol molecules?
a) one
b) two
c) three
d) four

14.8 a A general method for preparing alcohols is the

a) hydration of alkenes.
b) combustion of alkanes.
c) combustion of ethers.
d) hydrogenation of alkenes.

14.9 c Which of the following is a secondary alcohol?

a) CH3 CH2 CH2 CH2 OH

b) CH3 CH CH2 CH2 OH

CH3

c) CH3 CH2 CH2 CH OH

CH3

d) CH3 CH2 CH2 CH2

OH

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154 Chapter 14: Alcohols, Phenols, and Ethers Test Bank

14.10 b Intramolecular dehydration of an alcohol produces a(n)

a) alkane.
b) alkene.
c) ether.
d) thiol.

14.11 a [Algorithmic]Oxidation of a secondary alcohol produces a(n)

a) ketone.
b) aldehyde.
c) carboxylic acid.
d) ether.

14.12 b [Algorithmic]Which of the following statements concerning phenols is incorrect?

a) They are generally low-melting solids or oily liquids.
b) They are generally very soluble in water.
c) They are easily oxidized and therefore used as antioxidants.
d) Unlike alcohols, they are weak acids in solution.

OH
14.13 c [Algorithmic]The correct IUPAC name for is

Br Br
a) 1,3-dibromophenol.
b) 2,4-dibromophenol.
c) 3,5-dibromophenol.
d) 1,5-dibromophenol.

14.14 c [Algorithmic]All of the following general formulas except one represent an ether.
The exception is
a) R–O–R.
b) R–O–Ar.
c) R–O–H.
d) Ar–O–Ar.

14.15 a [Algorithmic]What is the IUPAC name for the ether whose common name is ethyl
propyl ether?
a) 1-ethoxypropane
b) 2-ethoxypropane
c) 1-propoxyethane
d) 2-propoxyethane

14.16 a In chemical reactivity, ethers resemble

a) alkanes.
b) alkenes.
c) alcohols.
d) phenols.

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Test Bank Chapter 14: Alcohols, Phenols, and Ethers 155

14.17 a The sulfhydryl functional group is found in

a) thiols.
b) disulfides.
c) both thiols and disulfides.
d) neither thiols nor disulfides.

14.18 c Which of the following is the structure for 1-propanethiol?

a) CH3 CH2 CH OH
SH

b) CH2 CH2 CH2 OH

SH

c) CH3 CH2 CH2 SH

d) CH2 CH2 CH2

SH OH

14.19 c Which of the following molecules contains both an alkoxy group and a hydroxy
group?
a) CH3 O CH3
b) CH3 O CH2 O CH3
c) CH3 O CH2 O H
d) CH3 CH2 O H

14.20 d [Algorithmic]In which of the following pairs of compounds are the two members of
the pair constitutional isomers?
a) methoxymethane and ethoxyethane
b) ethanol and ethanediol
c) propyl alcohol and dipropyl ether
d) isopropyl alcohol and methyl ethyl ether

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156 Chapter 14: Alcohols, Phenols, and Ethers Test Bank

TYPE II MULTIPLE-CHOICE QUESTIONS

In each of the following multiple-choice questions, place the letter of the correct response in the blank
at the left. There may be more than one correct response for a question (choice d) or no correct
response for a question (choice e).

14.21 c In which of the following pairs of names do both names represent the same alcohol?
a) 2-propanol and propyl alcohol
b) 1-propanol and isopropyl alcohol
c) 2-methyl-2-propanol and isobutyl alcohol
d) more than one correct response
e) no correct response

14.22 c Which of the following is a correct name-composition pairing for an alcohol?

a) 2-methylpentanol; 6 carbon atoms and 2 OH groups
b) ethylene glycol; 3 carbon atoms and 2 OH groups
c) glycerol; 3 carbon atoms and 3 OH groups
d) more than one correct response
e) no correct response

14.23 a The solubility of alcohols in water

a) decreases as the carbon chain length increases.
b) decreases as the number of –OH groups present increases.
c) increases with increasing molecular mass.
d) more than one correct response
e) no correct response

14.24 b In a secondary alcohol, the hydroxyl-bearing carbon atom

a) is always involved in a double bond.
b) is attached to two other carbon atoms.
c) cannot be bonded to hydrogen atoms.
d) more than one correct response
e) no correct response

14.25 c Which of the following conditions for an alcohol dehydration reaction with H2SO4 as
the catalyst will produce an ether?
a) 1º alcohol, 180ºC
b) 2º alcohol, 140ºC
c) 1º alcohol, 140ºC
d) more than one correct response
e) no correct response

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Test Bank Chapter 14: Alcohols, Phenols, and Ethers 157

14.26 e For which of the following intramolecular alcohol dehydrations is Saytzeff’s rule
needed to predict the structure of the alkene formed in the greatest amount?
a) 1-propanol
b) 2-propanol
c) 1-butanol
d) more than one correct response
e) no correct response

14.27 c For which of the following alcohol oxidations is the listed oxidation product
incorrect?
a) primary alcohol; aldehyde
b) secondary alcohol; ketone
c) tertiary alcohol; carboxylic acid
d) more than one correct response
e) no correct response

14.28 d Which of the following is an incorrect IUPAC name for a phenol derivative?
a) 1-chlorophenol
b) 2,5-dibromophenol
c) 3-methylphenol
d) more than one correct response
e) no correct response

14.29 a Ethers may be viewed as derivatives of water in which both hydrogen atoms have
been replaced with
a) hydrocarbon groups.
b) hydroxyl groups.
c) alkoxy groups.
d) more than one correct response
e) no correct response

14.30 c In which of the following pairs of names do both names represent the same ether?
a) diethyl ether and 1,2-diethoxyethane
b) methyl isopropyl ether and 1-methoxypropane
c) ethyl isopropyl ether and 2-ethoxypropane
d) more than one correct response
e) no correct response

14.31 a Which of the following is a characteristic property of thiols?

a) extremely strong odors
b) abnormally high boiling points
c) strong resistance to oxidation
d) more than one correct response
e) no correct response

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158 Chapter 14: Alcohols, Phenols, and Ethers Test Bank

14.32 e Which of the following pairings of names and general formulas is incorrect?
a) dithiol and HS–R–SH
b) thioether and R–S–R
c) disulfide and R–S–S–R
d) more than one correct response
e) no correct response

14.33 b Which of the following general types of compounds is always a heterocyclic

compound?
a) a substituted phenol
b) a cyclic ether
c) a cyclic compound with both hydroxy and alkoxy substituents on the ring
d) more than one correct response
e) no correct response

14.34 d Which of the following compounds contains two oxygen atoms?

a) 1,3-dimethoxybenzene
b) methoxycyclohexane
c) 2-ethoxy-1-propanol
d) more than one correct response
e) no correct response

14.35 e Which of the following compounds is not a constitutional isomer of 1-butanol?

a) diethyl ether
b) 2-methyl-2-propanol
c) 2-methoxypropane
d) more than one correct response
e) no correct response

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Test Bank Chapter 14: Alcohols, Phenols, and Ethers 159

MULTIPLE-CHOICE FORMAT TRUE-FALSE QUESTIONS

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.

14.36 b - TFT Statements:

(1) Common names for alcohols have two words and IUPAC names for alcohols
are only one word.
(2) Mild oxidizing agents readily oxidize tertiary alcohols.
(3) Cyclic ethers are examples of heterocyclic organic 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.

14.37 d - FFF Statements:

(1) Long-chain alcohols are generally more soluble in water than short-chain
alcohols.
(2) The compound ethyl methyl ether contains two alkoxy groups.
(3) Rubbing alcohol is a 50-50 mixture by volume of isopropyl alcohol and water.
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.

14.38 c - FTF Statements:

(1) Glycerin, a three-carbon diol, has a great affinity for moisture (water vapor).
(2) Oxidation of a thiol produces a disulfide.
(3) MTBE is a water-soluble polymeric alcohol.
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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160 Chapter 14: Alcohols, Phenols, and Ethers Test Bank

14.39 a - TTT Statements:

(1) Denatured alcohol is ethyl alcohol that has been rendered unfit to drink.
(2) The functional group present in the compound 2-butanethiol is the sulfhydryl
group.
(3) The simplest phenol, phenol itself, is a colorless solid with a medicinal odor.
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.

14.40 b - TTF Statements:

(1) Alcohols have higher boiling points than alkanes of similar molecular mass
because of hydrogen bonding.
(2) Ethylene glycol contains two carbon atoms and two hydroxyl groups.
(3) Primary and secondary alcohols give the same type of product when subjected
to mild oxidizing agents.
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.

14.41 a - TTT Statements:

(1) Intramolecular alcohol dehydration converts an alcohol to an alkene.
(2) An aryl group is an aromatic carbon-ring system from which one hydrogen
atom has been removed.
(3) Unlike alcohols, phenols are weak acids in solution.
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.

14.42 c - TFF Statements:

(1) Propyl alcohol and methoxyethane are constitutional isomers.
(2) Zaitsev’s rule is used in predicting the major organic product from
intermolecular alcohol dehydration.
(3) An older name for methyl alcohol is grain alcohol.
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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Test Bank Chapter 14: Alcohols, Phenols, and Ethers 161

14.43 b - TFT Statements:

(1) 2-propanol is a secondary alcohol.
(2) Each of the three methylphenols has a different common name.
(3) The compound 4-methoxy-2-butanol is both an alcohol and an ether.
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.

14.44 b - FTT Statements:

(1) Isopropyl alcohol and 1-propanol are two names for the same compound.
(2) Ether molecules cannot hydrogen bond to one another.
(3) Alcohol molecules have both polar and nonpolar character.
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.

14.45 b - TFT Statements:

(1) Menthol is a naturally occurring terpene alcohol with a minty odor.
(2) THC, the active ingredient in marijuana, contains phenol, cyclic ether and
halogen functional groups.
(3) Ether-type anesthetics in use today are usually halogenated 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.

MATCHING QUESTIONS

For each of the hydrocarbon derivatives on the left, select from the response list on the right the
correct molecular formula. Responses on the right may be used more than once or need not be used at
all.

14.46 a Ethoxyethane a) C4H10O

b) C4H12O
14.47 a Tertiary-butyl alcohol c) C4H10O2
d) C4H12O2
14.48 c 1,3-Butanediol

14.49 c 1,2-Dimethoxyethane

14.50 a 2-Methyl-1-propanol

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162 Chapter 14: Alcohols, Phenols, and Ethers Test Bank

Match the alcohol characteristics on the left with names in the response list on the right. Responses on
the right may be used more than once or need not be used at all.

14.51 d Contains 2 –OH groups a) drinking alcohol

b) rubbing alcohol
14.52 b Contains isopropyl alcohol c) glycerin
d) ethylene glycol
14.53 c Contains 3 –OH groups

14.54 a Contains 2 carbons and 1 –OH group

14.55 a Obtained from fermentation of grain products

Match the structural formulas on the left with compound types in the response list on the right.
Responses on the right may be used more than once or need not be used at all.

14.56 b CH3–S–S–CH3 a) thioether

b) disulfide
14.57 c HO–CH2–CH2–OH c) diol
d) thiol
14.58 a CH3–S–CH3

14.59 d CH3–CH2–SH

14.60 a CH3–CH2–S–CH3

For each pair of compounds on the left, select a correct structural characterization from the response
list on the right. Responses on the right may be used more than once or need not be used at all.

14.61 a 1-Butanol a) are constitutional isomers

2-Butanol b) have the same number of carbon atoms and
same number of oxygen atoms but are not
14.62 a 1-Methoxypropane constitutional isomers
Ethoxyethane c) have the same number of carbon atoms but a
different number of oxygen atoms
14.63 d 3-Chlorophenol d) have the same number of oxygen atoms but a
o-Cresol different number of carbon atoms

14.64 b Cyclohexanol
Phenol

14.65 c 1,3-Butanediol
Methyl isopropyl ether

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Test Bank Chapter 14: Alcohols, Phenols, and Ethers 163

For each set of reactants on the left, select a correct product characterization from the response list on
the right. Responses on the right may be used more than once or need not be used at all.

14.66 a Primary alcohol a) alkene

Sulfuric acid b) aldehyde
180ºC c) ether
d) ketone
14.67 a Secondary alcohol
Sulfuric acid
180ºC

14.68 a Secondary alcohol

Sulfuric acid
140ºC

14.69 b Primary alcohol

Mild oxidizing agent

14.70 d Secondary alcohol

Mild oxidizing agent

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