General, Organic & Biological Chemistry, 5e (Timberlake)
Chapter 13 Alcohols, Phenols, Thiols, and Ethers
13.1 Multiple-Choice Questions
1) Which one of the following compounds is an alcohol?
A) OH
|
CH3 – CH – CH3
B) O
CH3 – CH2 – CH
C) CH3 – CH = CH – CH2 – CH3
D) CH3 – CH2 – O – CH2 – CH3
E) CH3 – SH
2) The compound CH3 – CH2 – SH is in the organic family known as
A) ethers.
B) thiols.
C) alcohols.
D) sulfides.
E) amino acids.
3) Alcohols contain which functional group?
A) amine
B) amide
C) hydroxyl
D) thiol
4) What is the IUPAC name for this compound?
A) 3-methyl-1-hexanol
B) 3-methyl-1-pentanol
C) 3-methyl-5-pentanol
D) 3-methyl-6-hexanol
E) 3-methylpentanol
5) Which of the following is the IUPAC name for the compound below?
A) 5-methyl-4-hexanol
B) 5-methyl-4-pentanol
C) 2-methyl-3-hexanol
D) 2-methyl-3-pentanol
E) 2-methyl-3-heptanol
6) The condensed structural formula for 2,3-dichloro-4-methylcyclohexanol is
A)
B)
C)
D)
E)
7) What is the IUPAC name of this compound?
OH
|
CH3 – C – CH3
|
CH3
A) butanol
B) propanol
C) 2-propanol
D) 2-methylbutanol
E) 2-methyl-2-propanol
8) Which one of the following compounds is a thiol?
A) OH
|
CH3 – CH – CH3
B) O
CH3 – CH2 – CH
C) CH3 – CH = CH – CH2 – CH3
D) CH3 – CH2 – O – CH2 – CH3
E) CH3 – SH
9) What is the name for this compound?
A) 2-bromo-5-ethylcyclohexanol
B) 2-bromo-5-ethylphenol
C) 4-bromo-1-ethyl-5-phenol
D) 6-bromo-3-ethylphenol
E) 2-bromo-5-methylphenol
10) What is the name for this compound?
A) cyclopentanol
B) cyclohexanol
C) cyclobenzenol
D) phenol
E) glycerol
11) A phenol has an -OH group bonded to a(n)
A) singly substituted or unsubstituted carbon.
B) disubstituted carbon.
C) trisubstituted carbon.
D) aromatic carbon.
E) tetrasubstituted carbon.
12) Thiols have structures similar to alcohols except that they contain
A) three alcohol groups.
B) more than one carbon.
C) sulfur in place of oxygen in the functional group.
D) lithium in place of oxygen in the functional group.
E) nitrogen in place of oxygen in the functional group.
13) Methanol is used in all the following except
A) making plastics.
B) racing fuel.
C) alcoholic beverages.
D) solvents.
E) paint remover.
14) 1,2-ethanediol (ethylene diol) has uses that include
A) antifreeze.
B) solvent for paint.
C) production of synthetic fibers.
D) solvent for ink.
E) All of the above.
15) What is the IUPAC name for CH3 – CH2 – CH2 – SH?
A) 1-propanethiol
B) 2-propanethiol
C) 1-butanethiol
D) 2-butanethiol
E) propyl thiol
16) Thiols are strong-smelling compounds responsible for
A) fruity odors.
B) sharp odors.
C) flowery odors.
D) skunky or bad smelling odors.
E) salty odors.
17) What is the name of this compound?
A) cyclopentyl propyl ether
B) cyclopentyl propyl ketone
C) 1-cyclopropyl-1-propylalcohol
D) propylcyclopentanol
E) 3-cyclopentylpropanol
18) The common name for the compound CH3 – CH2 – CH2 – O – CH2 – CH3 is
A) 3-pentanol.
B) ethyl propyl ether.
C) 3-hexanol.
D) 3-ether pentane.
E) ethyl propyl ketone.
19) The common name of CH3 – CH2 – O – CH2 – CH3 is
A) dimethyl ether.
B) diethyl ether.
C) 2-etherbutane.
D) butyl ether.
E) dibutyl ether.
20) Why has diethyl ether been replaced as a general anesthetic?
A) It causes unpleasant side effects in many patients.
B) It is slightly polar.
C) It can hydrogen bond to water.
D) It is not very reactive.
E) It is slightly soluble in water.
21) What is the common name of the ether that is an isomer of 2-propanol?
A) isopropyl ether
B) diethyl ether
C) dimethyl ether
D) ethyl methyl ether
E) 1-propanol
22) What is the common name of the ether that is an isomer of 1-butanol?
A) isopropyl ether
B) diethyl ether
C) dimethyl ether
D) ethyl methyl ether
E) butyl ether
23) The alcohol in this list that would be most soluble in water is
A) ethanol.
B) 1-butanol.
C) 1-pentanol.
D) 1-hexanol.
E) 1-heptanol.
24) Which of the following compounds is a weak acid?
A) ethanol
B) ethanal
C) phenol
D) cyclohexanol
E) acetone
25) Which of the following compounds is a secondary alcohol?
A) CH3 – CH – O – CH3
|
CH3
B) CH3OH
C) OH
|
CH3 – CH2 – C – CH3
|
CH3
D) CH3
|
CH3 – C – CH3
|
OH
E) CH3 – CH – OH
|
CH3
26) 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
27) A primary alcohol has a hydroxyl group bonded to a(n)
A) singly substituted or unsubstituted carbon.
B) disubstituted carbon.
C) trisubstituted carbon.
D) aromatic carbon.
28) A secondary alcohol has a hydroxyl group bonded to a(n)
A) singly substituted or unsubstituted carbon.
B) disubstituted carbon.
C) trisubstituted carbon.
D) aromatic carbon.
29) A tertiary alcohol has a hydroxyl group bonded to a(n)
A) singly substituted or unsubstituted carbon.
B) disubstituted carbon.
C) trisubstituted carbon.
D) triple-bonded carbon.
E) double bonded carbon.
30) What kind of bonds do alcohols form between individual molecules?
A) oxygen bonds
B) hydrogen bonds
C) single bonds
D) carbon bonds
E) ionic bonds
31) The dehydration of an alcohol in the presence of a strong acid yields
A) an alkane.
B) an alkene.
C) a ketone.
D) an alcohol.
E) an aldehyde.
32) The dehydration product of CH3 – CH2 – CH2 – OH in the presence of acid is
A) CH2 = C = CH2.
B) cyclopropane.
C) cyclopropene.
D) propene.
E) propyne.
33) When 2-methyl-2-butanol undergoes dehydration in acid, one product is
A) 2-methyl-2-butene.
B) 2-methylbutanone.
C) 2-pentanone.
D) 2-methylbutanal.
E) hexene.
34) In the oxidation of an alcohol to a ketone, there is
A) a loss of hydrogen.
B) a loss of oxygen.
C) a loss of carbon.
D) a gain of hydrogen.
E) a gain of oxygen.
35) What is the product when this compound undergoes oxidation?
CH3
|
CH3 – C – CH2 – CH2 – OH
|
CH3
A) hexanal
B) 2,2-dimethylbutanal
C) 2,2-dimethyl-4-butanone
D) 3,3-dimethyl-1-butanone
E) 3,3-dimethylbutanal
36) What type of alcohol undergoes oxidation to yield a ketone?
A) primary alcohol
B) both primary and secondary alcohols
C) secondary alcohol
D) all classes of alcohols
E) both secondary and tertiary alcohols
37) Tertiary alcohols cannot be oxidized because
A) there are no oxygen atoms to remove from the alcohol carbon.
B) there are no hydrogen atoms attached to the alcohol carbon.
C) the alcohol carbon is bonded to four groups so no oxygen can be added to it.
D) the alcohol carbon is bonded to four groups so no hydrogen can be added to it.
E) the alcohol carbon is too electronegative to have hydrogen removed from it.
38) What type of alcohol is resistant to oxidation?
A) primary
B) secondary
C) tertiary
D) quaternary
E) none
39) What is the product when the following compound is oxidized?
A) a ketone
B) an alkene
C) an aldehyde
D) an ether
E) an alkane
40) Which compound will undergo oxidation to yield the following?
A) pentanol
B) cyclopentane
C) cyclopentanol
D) methylcyclobutanol
E) cyclopentene
41) In the dehydration of an alcohol to an alkene, what is produced in addition to the alkene?
A) water
B) hydrogen
C) oxygen
D) carbon dioxide
E) carbon monoxide
42) When a primary alcohol is completely oxidized, the product is
A) another alcohol.
B) a carboxylic acid.
C) an aldehyde.
D) an alkane.
E) a ketone.
43) Methanol is toxic because it is ________ by the liver to carboxylic acids.
A) reduced
B) protonated
C) oxidized
D) conjugated
E) hydrated
44) Secondary alcohols are oxidized to
A) carboxylic acids.
B) ketones.
C) aldehydes.
D) esters.
E) ethers.
45) Tertiary alcohols are oxidized to
A) secondary alcohols.
B) ketones.
C) aldehydes.
D) carboxylic acids.
E) None of the above.
46) Thiols can be gently oxidized to
A) disulfides.
B) aldehydes.
C) ketones.
D) carboxylic acids.
E) thioethers.
47) The dehydration product of OH in the presence of acid is
│
CH3 – CH– CH3
A) CH2 = C = CH2.
B) cyclopropane.
C) cyclopropene.
D) propene.
E) propyne.
13.2 True/False Questions
1) Alcohols, ethers, and phenols contain oxygen with only single bonds.
2) Alcohols, ethers, and thiols contain oxygen atoms.
3) Thiols usually have sweet odors.
4) 1,2,3-propanetriol is obtained during the manufacture of soap.
5) Glycerin strongly attracts and holds water, a property that makes it useful as a skin softener in
cosmetics.
6) Diethyl ether has been replaced by halogenated anesthetics, which have fewer side effects.
7) Ethers can only be straight chain compounds.
8) The following compound is ethyl propyl ether.
9) Alcohols form hydrogen bonds; this accounts for their higher boiling points when compared to similar–
sized alkanes.
10) The oxygen atom in alcohols decreases water solubility of the molecule.
11) Phenols behave as weak acids in water.
12) Alcohols can form hydrogen bonds.
13) Heptanol is a water soluble alcohol.
14) A secondary alcohol can be easily oxidized to a carboxylic acid.
15) Cycloalkanols are straight chain alcohols.
16) Alcohols can be dehydrated to form alkenes.
17) Primary alcohols can be oxidized to either aldehydes or ketones.
18) Secondary alcohols can be oxidized to ketones.
19) Tertiary alcohols are easily oxidized.
13.3 Matching Questions
Identify the product, if any, that would form in each of the following reactions.
A) O
CH3 – CH2 – C – CH3
B) O
CH3 – CH2 – CH
1) CH3 – CH2 – CH2 – OH
Objective: 13.4
Global Outcomes: GO2
2) CH3 – CH2 – CH – OH
|
CH3
Objective: 13.4
Global Outcomes: GO2
Match the structural formula with the correct functional group.
A) thiol
B) alcohol
C) ether
3) CH3 – CH2 – OH
Objective: 13.1
Global Outcomes: GO2
4) CH3 – CH2 – O – CH3
Objective: 13.1
Global Outcomes: GO2
5) CH3 – CH2 – SH
Objective: 13.1
Global Outcomes: GO2
Select the correct name for the following.
A) propanethiol
B) 1-ethyl-3- hydroxycyclohexene
C) propane sulfide
D) 3-ethylphenol
E) diethyl ether
6) CH3 – CH2 – CH2 – SH
Objective: 13.2
Global Outcomes: GO2
7) CH3 – CH2 – O – CH2 – CH3
Objective: 13.2
Global Outcomes: GO2
8)
Objective: 13.2
Global Outcomes: GO2
Classify the alcohols shown in column 1 as primary, secondary, or tertiary.
A) secondary
B) primary
C) tertiary
9) CH3 – CH2 – OH
Objective: 13.3
Global Outcomes: GO2
10) CH3
|
CH3 – C – CH2 – OH
|
CH3
Objective: 13.3
Global Outcomes: GO2
11) OH
|
CH3 – CH – CH3
Objective: 13.3
Global Outcomes: GO2
12)
Objective: 13.3
Global Outcomes: GO2
13) CH3
|
CH3 – C – CH2 – CH3
|
OH
Objective: 13.3
Global Outcomes: GO2