Deck 14: Alcohols, Phenols, and Ethers

Question 1

Which of the following statements concerning common alcohols is correct?

A) Wood alcohol and grain alcohol are the same substance.
B) Rubbing alcohol is pure ethyl alcohol.
C) Absolute alcohol is pure isopropanol.
D) Ethanol can be produced by fermentation.

Answer 1

Ethanol can be produced by fermentation.

Question 2

Which of the following statements concerning phenols is incorrect?

A) They are generally low-melting solids or oily liquids.
B) They easily dissolve in water.
C) Phenols can undergo halogenation.
D) Phenols have acid ionization constants lower than most weak inorganic acids.

Answer 2

They easily dissolve in water.

Question 3

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.

Answer 3

Hydrogen bonding occurs between alcohol molecules but not between alkane molecules.

Question 4

Which of the following is a secondary alcohol?

A)
B)
C)
D)

Question 5

In which of the following pairs of compounds are the two members of the pair constitutional isomers?

A) methoxymethane and ethoxyethane
B) butanol and butanediol
C) isopropyl alcohol and diisopropyl ether
D) isobutyl alcohol and diethyl ether

Question 6

In chemical reactivity, ethers resemble

A) alkanes
B) alkenes
C) alcohols
D) phenols

Question 7

The correct IUPAC name for is

A) hexyl dialcohol
B) 2,6-dihydroxyhexane
C) 2,6-hexanediol
D) 1,5-hexanediol

Question 8

The sulfhydryl functional group is found in

A) thiols
B) disulfides
C) both thiols and disulfides
D) neither thiols nor disulfides

Question 9

Intramolecular dehydration of an alcohol produces a(n)

A) alkane
B) alkene
C) ether
D) thiol

Question 10

The correct IUPAC name for is

A) isopropyl alcohol
B) 2-methyl ethanol
C) 2-propanol
D) hydroxypropane

Question 11

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

Question 12

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

A)
B)
C)
D)

Question 13

A general method for preparing alcohols is the

A) hydration of alkenes
B) combustion of alkanes
C) combustion of ethers
D) hydrogenation of alkenes

Question 14

The correct IUPAC name for is

A) 1,5-dibromophenol
B) 2,5-dibromophenol
C) 2,6-dibromophenol
D) 1,5-dibromophenol.

Question 15

Oxidation of a secondary alcohol produces a(n)

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

Question 16

In which of the following pairs of alcohols do both members of the pair contain two or more hydroxyl groups?

A) 2-methyl-2-propanol and propylene glycol
B) ethylene glycol and glycerol
C) butyl alcohol and propylene glycol
D) butanol and tert-butyl alcohol

Question 17

Which of the following molecules contains both an alkoxy group and a hydroxy group?

A)
B)
C)
D)

Question 18

All of the following general formulas except one represent an ether. The exception is

A) R-O-R
B) R-O-Ar
C) H-O-R
D) Ar-O-Ar

Question 19

How many hydrogen bonds can form between a methanol molecule and other methanol molecules?

A) one
B) two
C) three
D) four

Question 20

What is the IUPAC name for the ether whose common name is phenyl propyl ether?

A) propoxybenzene
B) 2-propoxybenzene
C) 1-phenoxypropane
D) 2-phenoxypropane

Question 21

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: (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.

Question 22

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

Question 23

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

Question 24

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

Question 25

Which of the following conditions for an alcohol dehydration reaction with H₂SO₄ as the catalyst will produce an ether?

A) 1 $\degree$ alcohol, 180 $\degree$ C
B) 2 $\degree$ alcohol, 140 $\degree$ C
C) 1 $\degree$ alcohol, 140 $\degree$ C
D) more than one correct response
E) no correct response

Question 26

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

Question 27

For which of the following intramolecular alcohol dehydrations is Zaitsev'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

Question 28

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

Question 29

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

Question 30

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

Question 31

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

Question 32

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: (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.

Question 33

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: (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.

Question 34

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

Question 35

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

Question 36

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: (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.

Question 37

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

Question 38

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

Question 39

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: (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.

Question 40

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

A) 2-methylpentanol; six carbon atoms and two OH groups
B) ethylene glycol; three carbon atoms and two OH groups
C) glycerol; three carbon atoms and three OH groups
D) more than one correct response
E) no correct response

Question 41

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: (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.

Question 42

Match the following structural formula with compound types in the response list: CH₃-S-CH₃.

A) thioether
B) disulfide
C) diol
D) thiol

Question 43

Match the following alcohol characteristic(s) with names in the response list: contains two carbons and one -OH group.

A) drinking alcohol
B) rubbing alcohol
C) glycerin
D) ethylene glycol

Question 44

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: (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.

Question 45

Match the following structural formula with compound types in the response list: HO-CH₂-CH₂-OH.

A) thioether
B) disulfide
C) diol
D) thiol

Question 46

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: (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.

Question 47

Match the following alcohol characteristic(s) with names in the response list: contains two -OH groups.

A) drinking alcohol
B) rubbing alcohol
C) glycerin
D) ethylene glycol

Question 48

Match the following structural formula with compound types in the response list: CH₃-CH₂-SH.

A) thioether
B) disulfide
C) diol
D) thiol

Question 49

Match the following alcohol characteristic(s) with names in the response list: obtained from fermentation of grain products.

A) drinking alcohol
B) rubbing alcohol
C) glycerin
D) ethylene glycol

Question 50

For the following hydrocarbon derivative, select from the response list the correct molecular formula: 1,2-dimethoxyethane.

A) C₄H₁₀O
B) C₄H₁₂O
C) C₄H₁₀O₂
D) C₄H₁₂O₂

Question 51

Match the following structural formula with compound types in the response list: CH₃-CH₂-S-CH₃.

A) thioether
B) disulfide
C) diol
D) thiol

Question 52

For the following hydrocarbon derivative, select from the response list the correct molecular formula: tertiary-butyl alcohol.

A) C₄H₁₀O
B) C₄H₁₂O
C) C₄H₁₀O₂
D) C₄H₁₂O₂

Question 53

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: (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.

Question 54

For the following hydrocarbon derivative, select from the response list the correct molecular formula: 1,3-butanediol.

A) C₄H₁₀O
B) C₄H₁₂O
C) C₄H₁₀O₂
D) C₄H₁₂O₂

Question 55

Match the following alcohol characteristic(s) with names in the response list: contains three -OH groups.

A) drinking alcohol
B) rubbing alcohol
C) glycerin
D) ethylene glycol

Question 56

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: (1) 2-Propanol is a secondary alcohol.
(2) Methylphenols are also called catechols.
(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.

Question 57

Match the following alcohol characteristic(s) with names in the response list: contains isopropyl alcohol.

A) drinking alcohol
B) rubbing alcohol
C) glycerin
D) ethylene glycol

Question 58

For the following hydrocarbon derivative, select from the response list the correct molecular formula: 2-methyl-1-propanol.

A) C₄H₁₀O
B) C₄H₁₂O
C) C₄H₁₀O₂
D) C₄H₁₂O₂

Question 59

For the following hydrocarbon derivative, select from the response list the correct molecular formula: ethoxyethane.

A) C₄H₁₀O
B) C₄H₁₂O
C) C₄H₁₀O₂
D) C₄H₁₂O₂

Question 60

Match the following structural formula with compound types in the response list: CH₃-S-S-CH.

A) thioether
B) disulfide
C) diol
D) thiol

Question 61

For the following pair of compounds, select a correct structural characterization from the response list: cyclohexanol and phenol.

A) are constitutional isomers
B) have the same number of carbon atoms and the same number of oxygen atoms but are not constitutional isomers
C) have the same number of carbon atoms but a different number of oxygen atoms
D) have the same number of oxygen atoms but a different number of carbon atoms

Question 62

For the following pair of compounds, select a correct structural characterization from the response list: 1-methoxypropane and ethoxyethane.

A) are constitutional isomers
B) have the same number of carbon atoms and the same number of oxygen atoms but are not constitutional isomers
C) have the same number of carbon atoms but a different number of oxygen atoms
D) have the same number of oxygen atoms but a different number of carbon atoms

Question 63

For the following pair of compounds, select a correct structural characterization from the response list: 1,3-butanediol and methyl isopropyl ether.

A) are constitutional isomers
B) have the same number of carbon atoms and the same number of oxygen atoms but are not constitutional isomers
C) have the same number of carbon atoms but a different number of oxygen atoms
D) have the same number of oxygen atoms but a different number of carbon atoms

Question 64

For the following set of reactants and reaction conditions, select a correct product characterization from the response list: secondary alcohol, sulfuric acid 140 $\degree$ C.

A) alkene
B) aldehyde
C) ether
D) ketone

Question 65

For the following pair of compounds, select a correct structural characterization from the response list: 3-chlorophenol and o-cresol.

A) are constitutional isomers
B) have the same number of carbon atoms and the same number of oxygen atoms but are not constitutional isomers
C) have the same number of carbon atoms but a different number of oxygen atoms
D) have the same number of oxygen atoms but a different number of carbon atoms

Question 66

For the following set of reactants and reaction conditions, select a correct product characterization from the response list: secondary alcohol, mild oxidizing agent.

A) alkene
B) aldehyde
C) ether
D) ketone

Question 67

For the following pair of compounds, select a correct structural characterization from the response list: 1-butanol and 2-butanol.

A) are constitutional isomers
B) have the same number of carbon atoms and the same number of oxygen atoms but are not constitutional isomers
C) have the same number of carbon atoms but a different number of oxygen atoms
D) have the same number of oxygen atoms but a different number of carbon atoms

Question 68

For the following set of reactants and reaction conditions, select a correct product characterization from the response list: primary alcohol, mild oxidizing agent.

A) alkene
B) aldehyde
C) ether
D) ketone

Question 69

For the following set of reactants and reaction conditions, select a correct product characterization from the response list: primary alcohol, sulfuric acid, 180 $\degree$ C.

A) alkene
B) aldehyde
C) ether
D) ketone

Question 70

For the following set of reactants and reaction conditions, select a correct product characterization from the response list: secondary alcohol, sulfuric acid 180 $\degree$ C.

A) alkene
B) aldehyde
C) ether
D) ketone