Deck 12: Alcohols, phenols, thiols, and Ethers

Question 1

What is the typical medical use for the compounds shown below?

A)antiseptics/disinfectants
B)antibiotics
C)anesthetics
D)radiation therapy
E)suture material

Answer 1

anesthetics

Question 2

What is the most common use of phenol derivatives in health care?

A)antiseptics/disinfectants
B)antibiotics
C)anesthetics
D)radiation therapy
E)suture material

Answer 2

antiseptics/disinfectants

Question 3

Which of the following statements about the compound shown below is FALSE?

A)It is a tertiary alcohol.
B)Its name is 2-methyl-3-pentanol.
C)It can participate in hydrogen bonding.
D)It can be oxidized to a ketone.
E)It contains both a nonpolar and a polar region.

Answer 3

It is a tertiary alcohol.

Question 4

Which statement concerning the physical properties of alcohols is FALSE?

A)Alcohols are polar and can form intermolecular hydrogen bonds.
B)1-Pentanol is more water-soluble than pentane because 1-pentanol can hydrogen bond with water.
C)The water solubility of an alcohol decreases with an increase in the hydrocarbon chain.
D)Alcohols have higher boiling point temperatures than hydrocarbons and ethers of similar molar mass.
E)The water solubility of an alcohol decreases with an increase in the number of polar hydroxyl groups.

Question 5

What class of compounds is represented by the general formula RSH?

A)alcohols
B)ethers
C)thiols
D)phenols
E)disulfides

Question 6

What is the IUPAC name of the compound shown below?

A)1-propanol
B)1-cyclopentanol
C)cyclopropanol
D)phenol
E)glycerol

Question 7

The compound tetrahydrocannabinol (THC)is partly responsible for the "high" associated with smoking marijuana.Which of the following correctly represents the organic families to which THC belongs?

A)alcohol,ether,alkene
B)phenol,alkene,ether
C)thiol,phenol,alkene
D)alcohol,thiol,alkene
E)ester,phenol,alcohol

Question 8

Which of the following is the structure for methyl tertiary butyl ether?

A)

B)

C)

D)

E)
$\mathrm { CH } _ { 3 } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$

Question 9

What is another acceptable name for the compound 4-chlorophenol?

A)meta-4-chlorophenol
B)para-chlorophenol
C)meta-chlorophenol
D)ortho-chlorophenol
E)trans-4-chlorophenol

Question 10

What important type of bond,formed between two sulfhydryl (-SH)groups,plays a key role in the shapes of many proteins?

A)cysteine bond
B)hydrogen bond
C)disulfide bond
D)thioester bond
E)double bond

Question 11

Which product of the oxidation of ethanol causes many of the symptoms of the "morning-after hangover"?

A)phenol
B)resveratrol
C)ethanal
D)formaldehyde
E)ethylene glycol

Question 12

When methanal,the simplest aldehyde,undergoes reduction by the addition of hydrogen,what product results?

A)methanol
B)methane
C)methanone
D)formaldehyde
E)carbon dioxide

Question 13

Which class of compounds is primarily responsible for the foul smell of skunk spray?

A)phenols
B)thiols
C)diols
D)acetals
E)ketones

Question 14

Hexylresorcinol is listed as an active ingredient in some mouthwashes and throat lozenges.The IUPAC name for hexylresorcinol is 4-hexyl-3-hydroxyphenol.Which of the following is its structure?

A)

B)

C)

D)

E)

Question 15

Which of the following is NOT a possible alkene product from the dehydration reaction of 2-butanol?

A)

B)

C)

D)

E)All of these choices are correct.

Question 16

Cortisol is an anti-inflammatory agent that also regulates carbohydrate metabolism.Which of the following best describes the types of alcohols present in cortisol?

A)primary,secondary,and tertiary
B)secondary and tertiary
C)primary,tertiary,and a phenol
D)primary,secondary,and quaternary
E)primary and tertiary

Question 17

Which of the following is the structure of ethyl propyl ether?

A)
$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
B)

C)

D)

E)

Question 18

The IUPAC name for the compound shown below is 1,2,3-propanetriol.What is the common name of this compound?

A)glycerol
B)ethylene glycol
C)phenol
D)isopropyl alcohol
E)menthol

Question 19

What is the IUPAC name of the compound CH₃CH₂CH₂OH?

A)propanol
B)ethanol
C)3-phenol
D)1-propanol
E)3-pentanol

Question 20

What is the general classification of the reaction depicted below?

A)substitution
B)oxidation
C)addition
D)reduction
E)condensation

Question 21

What is the IUPAC name of the following compound?

A)2-methyl-3-hexanol
B)5-methyl-4-hexanol
C)3-methyl-2-hexanol
D)2-methyl-3-pentanol
E)2,2-dimethyl-3-pentanol

Question 22

What alcohol can cause blindness and possibly death when it is consumed?

A)ethanal
B)ethanol
C)methanal
D)methanol
E)1,2,3-propanetriol

Question 23

What class of compounds is represented by the general formula ROR?

A)alcohols
B)esters
C)ethers
D)aldehydes
E)carboxylic acids

Question 24

The reduction of acetaldehyde (shown below)is an important biochemical reaction.Which of the following is the product of its reduction?

A)CH₃CH₂OH
B)CH₃CH₃
C)

D)

E)

Question 25

What is the name of the simplest alcohol?

A)primol
B)methanal
C)methanol
D)ethanol
E)formal

Question 26

Although ethanol is fit for human consumption,methanol is quite toxic if ingested.The toxicity is due to the aldehyde produced when methanol is oxidized in the liver.Which of the following is the aldehyde formed by the oxidation of methanol?

A)

B)

C)

D)

E)

Question 27

Oxidation of a secondary alcohol results in what type of compound?

A)alkene
B)aldehyde
C)carboxylic acid
D)ketone
E)ether

Question 28

What is the name of the alcohol produced by the fermentation of sugars and starches,and contained in alcoholic beverages?

A)methyl alcohol
B)propanol
C)isopropyl alcohol
D)ethanol
E)methanol

Question 29

The dehydration of an alcohol produces what type of organic compound?

A)alkane
B)alkene
C)alkyne
D)aldehyde
E)ketone

Question 30

What is the structure of the ether,3-ethoxyhexane?

A)

B)CH₃CH₂OCH₂CH₂CH₂CH₂CH₂CH₃
C)

D)

E)None of the choices are correct.

Question 31

Which statement best describes the solubility of the alcohol whose structure is shown below?

A)It would be readily soluble in water because it contains a polar hydroxyl group.
B)It would be very soluble in water because it can hydrogen bond with water.
C)It would have limited solubility in water because the molecule is largely hydrophobic.
D)It would be soluble in NaCl(aq)because it can dissociate into ions.
E)It is impossible to predict solubility from the structure alone.

Question 32

Which of the following structures represents the compound 1,3-propanedithiol?

A)H₂SCH₂CH₂CH₂SH₂
B)HSCH₂CH(SH)CH₃
C)HSCH₂CH₂CH₂SH
D)S CHCH₂CH
S
E)None of the choices are correct.

Question 33

Dehydration of the alcohol shown below produces styrene,an important starting material in the polymer and plastics industry.What is the structure of styrene?

A)

B)

C)

D)

E)

Question 34

Which type of alcohol does NOT undergo oxidation under normal conditions?

A)primary
B)secondary
C)tertiary
D)Neither secondary nor tertiary alcohols under go oxidation.
E)All alcohols undergo oxidation.

Question 35

Ethylene glycol is the common name for the compound with the structure: HOCH₂CH₂OH.What is the IUPAC name for this compound?

A)1,2-diethanol
B)1,2-phenol
C)propanol
D)dihydroxyethane
E)1,2-ethanediol

Question 36

What role does the thiol coenzyme A perform in biochemical reactions?

A)It serves as the energy source for energy-requiring reactions.
B)It serves as a carrier of two-carbon acetyl groups.
C)It serves as an identification marker on the surface of cells.
D)It functions as a catalyst for reduction reactions.
E)It is a structural component of muscle and bone.

Question 37

Classify the alcohol shown below.

A)primary
B)secondary
C)tertiary
D)quaternary
E)phenol

Question 38

What is the name of the product formed in the following reaction,the catalyzed hydrogenation of butanone? $+\mathrm{H}_{2} \stackrel{\text { catalyst }}{\longrightarrow} \text { ? }$

A)butane
B)isobutyl alcohol
C)2-butanol
D)butanol
E)butanal

Question 39

What is the common name of the simplest ether?

A)dimethyl ether
B)methyl ether
C)1,2-dimethylether
D)ethyl ether
E)methyl ethyl ether

Question 40

Zaitsev's rule can be used to predict the major alkene product in a dehydration reaction.Which of the following alkenes would be the major product of the dehydration reaction shown below?

A)

B)

C)

D)

E)All are equally likely.

Question 41

What type of compound is produced by the hydration of an alkene?

A)aldehyde
B)phenol
C)alcohol
D)diol
E)acid

Question 42

What type of compound is produced by the reduction of aldehydes and ketones?

A)alkene
B)phenol
C)alkane
D)carboxylic acid
E)alcohol

Question 43

The condensation reaction between the two alcohols below produces what type of compound?

A)alkene
B)alkane
C)carboxylic acid
D)ester
E)ether

Question 44

The hydration reaction below follows Markovnikov's rule.Which of the following is the expected major product of this reaction?

A)

B)

C)

D)

E)

Question 45

Which of the following alcohols is a tertiary alcohol?

A)1-butanol
B)2-butanol
C)2-methyl-1-butanol
D)2-methyl-2-butanol
E)3,3-dimethyl-2-butanol

Question 46

What is the initial oxidation product of a primary alcohol?

A)alkane
B)alkene
C)ketone
D)aldehyde
E)carboxylic acid

Question 47

What is the name of the product of the reaction below,which requires acid as a catalyst? CH₂=CH₂ + H₂O → ?

A)ethanol
B)ethanal
C)methanal
D)methanol
E)1,2,3-propanetriol

Question 48

Which of the following statements concerning glycerol is FALSE?

A)Glycerol contains three hydroxyl groups.
B)Glycerol is a viscous liquid.
C)Glycerol is sweet.
D)Glycerol is a diol.
E)Glycerol is obtained as a by-product of the hydrolysis of fats

Question 49

Which compound has been improperly named?

A)

B)

C)

D)

E)All are properly named.

Question 50

When an alcohol is heated with concentrated sulfuric acid (H₂SO₄),which of the following reaction types is likely to occur?

A)hydration
B)dehydration
C)dehydrogenation
D)oxidation
E)substitution

Question 51

Which of the following is expected to have the greatest solubility in water?

A)CH₃OH
B)CH₃CH₂CH₂CH₂OH
C)CH₃CH₂CH₂CH₂CH₃
D)CH₃CH₃
E)Both CH₃OH and CH₃CH₃ are correct.

Question 52

Which of the following compounds has the highest boiling point?

A)CH₂(OH)CH(OH)CH₂OH (molar mass = 92 g/mol)
B)CH₂(OH)CH₂CH₂CH₂OH (molar mass = 90 g/mol)
C)CH₃CH₂CH₂CH₂CH₂OH (molar mass = 88 g/mol)
D)CH₃CH(OH)CH₂CH₂OH (molar mass = 90 g/mol)
E)CH₃CH₂CH₂CH₂CH₂CH₃ (molar mass = 86 g/mol)

Question 53

Glycerol (1,2,3-propanetriol)is a by-product of the hydrolysis of fats.

Question 54

Which statement best explains why alcohols have a higher boiling point than alkanes with a similar molar mass?

A)Alcohols have weaker intermolecular forces than alkanes.
B)Alcohols have London dispersion forces only and alkanes have dipole-dipole attractions.
C)Alcohols have strong hydrogen bonding forces between molecules and alkanes have weaker London dispersion forces.
D)Alcohols have stronger London dispersion forces than alkanes.
E)None of the choices are correct.

Question 55

Which one of the following biochemical species contains a thioester bond that plays a key role in its function?

A)NAD⁺
B)NADH
C)DNA
D)acetyl CoA
E)ADP

Question 56

What is the common name of 2-propanol?

A)wood alcohol
B)grain alcohol
C)ethyl alcohol
D)propyl alcohol
E)isopropyl alcohol

Question 57

What is the IUPAC name for the following alcohol?

A)5-chloro-4-hexanol
B)2-chloro-3-hexanol
C)1-ethylchloro-butanol
D)3-chloro-4-butanol
E)1-chloro-1-methyl-2-pentanol

Question 58

Which of the following will result in the formation of an alkene?

A)oxidation of an aldehyde
B)hydration of an alcohol with nickel or platinum as a catalyst
C)dehydration of an alcohol by heating with concentrated sulfuric acid
D)reduction of an alcohol by the addition of FeCl₃
E)Both oxidation of an aldehyde and hydration of an alcohol with nickel or platinum as a catalyst are correct.

Question 59

Lactic acid gives sour milk its distinctive taste.What product is formed when lactic acid is oxidized?

A)

B)

C)

D)

E)

Question 60

Which of the following is a tertiary (3°)alcohol?

A)propanol
B)2-methyl-2-butanol
C)3-hexanol
D)1,2-ethanediol
E)cyclopropanol

Question 61

Liquid diethyl ether contains an extensive network of hydrogen bonds.

Question 62

The gain of an electron by an atom is called reduction.

Question 63

A primary alcohol has two alkyl groups attached to the carbinol carbon.

Question 64

The oxidation of a tertiary alcohol produces a ketone.

Question 65

Oxidation may be classified as the gain of bonds to oxygen,or the loss of bonds to hydrogen.

Question 66

Stepwise oxidation of a primary alcohol first produces an ether and then a carboxylic acid.

Question 67

Dehydration of a primary alcohol produces a mixture of alkenes.

Question 68

A phenol is a compound that contains a hydroxyl group attached to a benzene ring.

Question 69

The formation of a disulfide bond (-S-S-)between two sulfhydryl groups (-SH)is an oxidation process.