Alcohols, Phenols, Thiols, and Ethers Exam Prep Chapter 12

General, Organic, and Biochemistry, 10e (Denniston)

Chapter 12 Alcohols, Phenols, Thiols, and Ethers

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

A) alcohols

B) ethers

C) thiols

D) phenols

E) disulfides

2) 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

3) 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

4) What is the IUPAC name of the compound CH3CH2CH2OH?

A) propanol

B) ethanol

C) 3-phenol

D) 1-propanol

E) 3-pentanol

5) 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

6) What is the IUPAC name of the compound shown below?

A) 1-propanol

B) 1-cyclopentanol

C) cyclopropanol

D) phenol

E) glycerol

7) 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.

8) 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)

9) 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

10) 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

11) 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.

12) What is the general classification of the reaction depicted below?

A) substitution

B) oxidation

C) addition

D) reduction

E) condensation

13) 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

14) 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

15) 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.

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

A) antiseptics/disinfectants

B) antibiotics

C) anesthetics

D) radiation therapy

E) suture material

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

A)

B)

C)

D)

E)

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

A)

B)

C)

D)

E)

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

A) phenols

B) thiols

C) diols

D) acetals

E) ketones

20) 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

21) 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.

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

A) alcohols

B) esters

C) ethers

D) aldehydes

E) carboxylic acids

23) 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

24) 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

25) Classify the alcohol shown below.

A) primary

B) secondary

C) tertiary

D) quaternary

E) phenol

26) What is the name of the product formed in the following reaction, the catalyzed hydrogenation of butanone?

A) butane

B) isobutyl alcohol

C) 2-butanol

D) butanol

E) butanal

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

A) alkane

B) alkene

C) alkyne

D) aldehyde

E) ketone

28) 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.

29) 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.

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

A) alkene

B) aldehyde

C) carboxylic acid

D) ketone

E) ether

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

A)

B) CH3CH2OCH2CH2CH2CH2CH2CH3

C)

D)

E) None of the choices are correct.

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

A) H2SCH2CH2CH2SH2

B) HSCH2CH(SH)CH3

C) HSCH2CH2CH2SH

D) SCHCH2CHS

E) None of the choices are correct.

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)

34) What is the name of the simplest alcohol?

A) primol

B) methanal

C) methanol

D) ethanol

E) formal

35) 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)

36) 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

37) 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)

38) 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

39) 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

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.

41) 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

42) 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

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

A) aldehyde

B) phenol

C) alcohol

D) diol

E) acid

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

A) alkene

B) phenol

C) alkane

D) carboxylic acid

E) alcohol

45) 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

46) 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)

47) What is the initial oxidation product of a primary alcohol?

A) alkane

B) alkene

C) ketone

D) aldehyde

E) carboxylic acid

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

A) alkene

B) alkane

C) carboxylic acid

D) ester

E) ether

49) 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

50) Which compound has been improperly named?

A)

B)

C)

D)

E) All are properly named.

51) 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)

52) 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.

53) 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

54) 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.

55) What is the common name of 2-propanol?

A) wood alcohol

B) grain alcohol

C) ethyl alcohol

D) propyl alcohol

E) isopropyl alcohol

56) 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

57) 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

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.

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

A)

B)

C)

D)

E)

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

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

62) Dehydration of a primary alcohol produces a mixture of alkenes.

63) The oxidation of a tertiary alcohol produces a ketone.

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

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

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

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

68) Liquid diethyl ether contains an extensive network of hydrogen bonds.

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