Deck 13: Alcohols, Ethers, and Thiols

Question 1

What is the IUPAC name of the following compound?

A) methyl propyl methanol
B) 2-pentanol
C) 1-methyl-1-butanol
D) 4-pentanol

Answer 1

B

Question 2

Which of the following is the IUPAC name of butyl alcohol?

A) 1-butanol
B) 2-butanol
C) 2-methyl-1-propanol
D) 2-methyl-2-propanol

Answer 2

A

Question 3

Which of the following statements is true of cis-3-isopropylcyclohexanol?

A) Both the hydroxyl and the isopropyl groups lie in the plane that contains the cyclohexane ring.
B) Both the hydroxyl group and the isopropyl group lie above the plane that contains the cyclohexane ring.
C) The hydroxyl group lies above and the isopropyl group lies below the plane that contains the cyclohexane ring.
D) The hydroxyl group and the isopropyl group are bonded to the same carbon atom, and both groups lie in the same plane that contains the cyclohexane ring.

Answer 3

B

Question 4

Which of the following is the IUPAC name of sec-butyl alcohol?

A) 1-butanol
B) 2-butanol
C) 2-methyl-1-propanol
D) 2-methyl-2-propanol

Question 5

Which of the following compounds is likely to have an unpleasant odor?

A) CH₃CH₂OH
B) CH₃CH₂OCH₂CH₃
C) CH₃CH₂SH
D) HOCH₂CH₂OH

Question 6

Which of the following is the IUPAC name of tert-butyl alcohol?

A) 1-butanol
B) 2-butanol
C) 2-methyl-1-propanol
D) 2-methyl-2-propanol

Question 7

What are the positions of the ethyl and hydroxyl groups in cis-3-ethylcyclohexanol?

A) hydroxyl group: position 3 and ethyl group: position 1
B) hydroxyl group: position 1 and ethyl group: position 1
C) hydroxyl group: position 3 and ethyl group: position 2
D) hydroxyl group: position 1 and ethyl group: position 1

Question 8

Which of the following structures represents 4-methylcyclohexanol?

A)
B)
C)
D)

Question 9

What is the approximate H-C-O bond angle in an alcohol?

A) 90°
B) 109°
C) 120°
D) 180°

Question 10

Which of the following is a glycol?

A) HOCH₂CH₂CH₂OH
B)
C) HOCH₂CH₂OH
D) HOCH₂CH₂COOH

Question 11

What is the characteristic functional group of thiols?

A) -NH
B) -OH
C) -PH
D) -SH

Question 12

Which of the following statements is true?

A) All diols are glycols.
B) All glycols contain both a primary and a secondary alcohol.
C) All glycols are diols.
D) All glycols must have at least three carbon atoms.

Question 13

Identify a true statement about trans-2-methylcyclohexanol.

A) The hydroxyl group and the methyl group lie in the plane that contains the cyclohexane ring.
B) The methyl group may lie above and the hydroxyl group may lie below the plane that contains the cyclohexane ring.
C) The methyl group and the hydroxyl group lie above the plane that contains the cyclohexane ring.
D) The methyl group and the hydroxyl group lie below the plane that contains the cyclohexane ring.

Question 14

Which of the following is the IUPAC name of isobutyl alcohol?

A) 1-butanol
B) 2-butanol
C) 2-methyl-1-propanol
D) 2-methyl-2-propanol

Question 15

Which of the following is a glycol?

A) HOCH₂CH₂CH₂CH₂CH₂OH
B)
C) both HOCH2CH2CH2CH2CH2OH and
D) none of these

Question 16

What is the geometry at the hydroxyl-bearing carbon atom of an alcohol?

A) linear
B) tetrahedral
C) trigonal planar
D) trigonal pyramidal

Question 17

What is the IUPAC name of the following compound?

A) 2,2-dimethyl-4-butanol
B) 3,3-dimethyl-1-butanol
C) 1-tert-butyl-2-ethanol
D) 2-sec-butyl-1-ethanol

Question 18

What is the IUPAC name of the following compound?

A) 2-methyl-4-hexanol
B) 5-methyl-3-hexanol
C) 3-hydroxy-5-methylhexane
D) 4-hydroxy-2-methylhexane

Question 19

What is the IUPAC name of the following compound?

A) 2-ethyl-4-pentanol
B) 4-methyl-2-hexanol
C) 4-ethyl-2-pentanol
D) 3-methyl-5-hexanol

Question 20

Which of the following structures represents 3,3-dimethyl-1-butanol?

A)
B)
C)
D)

Question 21

Which of the following statements is true of London dispersion forces?

A) London dispersion forces are stronger between the molecules of 1-butanol than between the molecules of 2-methyl-2-propanol.
B) London dispersion forces are weaker than hydrogen bonding interactions.
C) London dispersion forces are stronger between the molecules of 1-butanol than between the molecules of 2-methyl-2-propanol and are weaker than hydrogen bonding interactions.
D) None of these

Question 22

Which of the following statements is true of the hydroxyl functional groups in 1,3-propanediol?

A) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon.
B) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon.
C) Both the hydroxyl groups are bonded to a 1° carbon each.
D) Neither of the hydroxyl groups is bonded to a 1° carbon.

Question 23

Which of the following classes of compounds react with sodium hydroxide to give a water-soluble salt?

A) primary alcohols
B) phenols
C) both primary alcohols and phenols
D) neither primary alcohols nor phenols

Question 24

Identify a statement that is true of the hydroxyl functional groups in 1,2,3-propanetriol.

A) Two hydroxyl groups are bonded to two 1° carbons, and the third hydroxyl group is bonded to a 3° carbon.
B) Two hydroxyl groups are bonded to two 2° carbons, and the third hydroxyl group is bonded to a 3° carbon.
C) Two hydroxyl groups are bonded to two 3° carbons, and the third hydroxyl group is bonded to a 2° carbon.
D) Two hydroxyl groups are bonded to two 1° carbons, and the third hydroxyl group is bonded to a 2° carbon.

Question 25

Which of the following is true of alcohols and phenols?

A) Both have equal basic strength.
B) Both have equal acidic strength.
C) Phenols are more acidic than alcohols.
D) Alcohols are more acidic than phenols.

Question 26

Which of the following compounds is the most soluble in water?

A) 1-pentanol
B) propane
C) 1-propanol
D) trans-2-butene

Question 27

Which of the following statements is true of the hydroxyl functional groups in 1,3-butanediol?

A) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon.
B) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon.
C) Both the hydroxyl groups are bonded to a 1° carbon each.
D) Neither of the hydroxyl groups is bonded to a 1° carbon.

Question 28

Which of the following alcohols has the lowest boiling point?

A) 1-pentanol
B) 1-octanol
C) 1-hexanol
D) 1-heptanol

Question 29

Which of the following alcohols is the least soluble in water?

A) 1-pentanol
B) 1-octanol
C) 1-hexanol
D) 2-propanol

Question 30

What is the correct order for the ease of dehydrating alcohols?

A) tertiary > secondary > primary
B) tertiary > primary > secondary
C) primary > secondary > tertiary
D) secondary > tertiary > primary

Question 31

What is the maximum number of hydrogen bonds that an ethanol molecule can form with other molecules?

A) 1
B) 2
C) 3
D) 4

Question 32

Which of the following is a primary alcohol?

A) 2-methyl-2-propanol
B) 4-methyl-2-pentanol
C) trans-2-methylcyclohexanol
D) 2,2-dimethyl-1-propanol

Question 33

Which of the following statements is true of the hydroxyl functional groups in 2-methyl-1,2-propanediol?

A) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon.
B) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon.
C) Both the hydroxyl groups are bonded to a 1° carbon each.
D) Neither of the hydroxyl groups is bonded to a 1° carbon.

Question 34

Which of the following statements is true of the hydroxyl functional groups in 2,3-butanediol?

A) One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon.
B) Both the hydroxyl groups are bonded to a 2° carbon each.
C) Both the hydroxyl groups are bonded to a 3° carbon each.
D) None of these is true.

Question 35

Which of the following alcohols has the highest boiling point?

A) 1-pentanol
B) 1,5-pentanediol
C) 1,3,5-pentanetriol
D) 1-butanol

Question 36

What is the approximate strength of a hydrogen bond in alcohols?

A) less than 1 kcal/mol
B) 2-5 kcal/mol
C) 10-20 kcal/mol
D) more than 20 kcal/mol

Question 37

Identify a polar covalent bond in 3-buten-1-ol.

A) carbon-carbon single bond
B) carbon-carbon single bond
C) oxygen-hydrogen bond
D) carbon-hydrogen bond

Question 38

Which statement is true of the polarities of the C-O and O-H bonds in alcohols?

A) Neither the C-O nor the O-H bond is polar.
B) The C-O and O-H bonds are equally polar.
C) Both bonds are polar, but the C-O bond is less polar than the O-H bond.
D) Both bonds are polar, but the O-H bond is less polar than the C-O bond.

Question 39

Which of the following is a starting material in the synthesis of nitroglycerin?

A) ethylene glycol
B) 1,2-propanediol
C) 1,3-propanediol
D) 1,2,3-propanetriol

Question 40

Why is the boiling point of ethanol greater than the boiling point of ethane?

A) because ethanol is nonpolar, whereas ethane is polar
B) because unlike ethane, ethanol contains nonpolar covalent bonds
C) because unlike ethane, ethanol contains hydrogen bonds
D) because ethanol is aromatic, whereas ethane is aliphatic

Question 41

Which of the following describes the products formed by the dehydration of 2,2,4,4-tetramethyl-3-pentanol?

A) The only product formed is 2,2,4,4-tetramethyl-2-pentene.
B) The only product formed is 2,2,4,4-tetramethyl-3-pentene.
C) The major product is 2,2,4,4-tetramethyl-2-pentene, and the minor product is 2,2,4,4-tetramethyl-3-pentene.
D) There is no product formed because 2,2,4,4-tetramethyl-3-pentanol does not undergo dehydration.

Question 42

How many different alkene products (counting the cis and trans isomers of a compound as a single product) can be formed when 2,3-dimethyl-3-pentanol is dehydrated?

A) 1
B) 2
C) 3
D) 4

Question 43

In which class of compounds is the carbon at the functional group least oxidized?

A) alcohols
B) aldehydes
C) carboxylic acids
D) ketones

Question 44

When heated with concentrated sulfuric acid, which of the following alcohols will be converted to the following alkene as the major product?

A)
B)
C) both and

D) none of these

Question 45

Which of the following is true of the hydration-dehydration equilibrium that exists between alcohols and alkenes under aqueous acidic conditions?

A) It lies so far in one direction that it can only be used for the preparation of alcohols.
B) It lies so far in one direction that it can only be used for the preparation of alkenes.
C) Reaction conditions can be adjusted so that the equilibrium can be used to prepare either alcohols or alkenes in high yields.
D) It is not useful for the preparation of either alcohols or alkenes.

Question 46

Which of the following alcohols will most easily undergo acid-catalyzed dehydration?

A) 1-butanol
B) 2-butanol
C) 2-methyl-2-propanol
D) 2-methyl-1-propanol

Question 47

What is the major product obtained from the dehydration of 2,3-dimethyl-3-pentanol?

A) 2-isopropyl-2-butene
B) 2,3-dimethyl-2-pentene
C) 3,4-dimethyl-2-pentene
D) 4,4-dimethyl-2-pentene

Question 48

Which of the following statements is true of oxidation reactions in primary or secondary alcohols?

A) The alcohols lose oxygen atoms when oxidized.
B) The alcohols gain electrons when oxidized.
C) The alcohols lose hydrogen atoms when oxidized.
D) The alcohols lose water when oxidized.

Question 49

Dehydration of which type of alcohol can never result in a mixture of products?

A) 1°
B) 2°
C) 3°
D) None, mixtures can be obtained from any of these.

Question 50

When 1-pentanol, 2-pentanol, and 3-pentanol are dehydrated, which compound among them will yield only a single alkene product?

A) only 1-pentanol
B) both 1-pentanol and 2-pentanol
C) both 1-pentanol and 3-pentanol
D) only 2-pentanol

Question 51

Which of the following statements is true of the products formed by the dehydration of trans-4-methylcyclohexanol?

A) The only product formed is 4-methylcyclohexene.
B) The only product formed is 5-methylcyclohexene.
C) The major product is 4-methylcyclohexene, and the minor product is 5-methylcyclohexene.
D) The major product is 5-methylcyclohexene, and the minor product is 4-methylcyclohexene.

Question 52

Suppose you carried out two reactions in sequence. In the first reaction, you hydrated 1-hexene; in the second reaction, you dehydrated the product(s) of the first reaction. Which of the following would be the major final product?

A) 1-hexene
B) 2-hexene
C) 3-hexene
D) 2-methyl-3-pentene

Question 53

Which of the following statements is true of the products formed by heating the given compound with concentrated sulfuric acid?

A) The major product is 2-methyl-2-hexene, and the minor product is 2-methyl-3-hexene.
B) The major product is 2-methyl-3-hexene, and the minor product is 2-methyl-2-hexene.
C) The only product formed is 2-methyl-1-hexene.
D) The only product formed is 2-methyl-3-hexene.

Question 54

Which of these compounds is obtained as the major product from the reaction of the following alkene with aqueous sulfuric acid?

A)
B)
C)
D)

Question 55

How many different alkene products (counting the cis and trans isomers of a compound as a single product) can be produced when 3-methyl-3-pentanol is dehydrated?

A) 1
B) 2
C) 3
D) 4

Question 56

Which of the following statements is true of the oxidation of tertiary alcohols?

A) It involves the loss of oxygen.
B) It involves the gain of electrons.
C) The oxidation of tertiary alcohols produces ethers.
D) Tertiary alcohols resist oxidation.

Question 57

Which of the following describes the products formed by the dehydration of cis-2-methylcyclopentanol?

A) The only product formed is 1-methylcyclopentene.
B) The only product formed is 3-methylcyclopentene.
C) The major product is 1-methylcyclopentene, and the minor product is 3-methylcyclopentene.
D) The major product is 3-methylcyclopentene, and the minor product is 1-methylcyclopentene.

Question 58

In which class of compounds is the carbon at the functional group most highly oxidized?

A) alcohols
B) aldehydes
C) carboxylic acids
D) ketones

Question 59

Which of the following products is formed by the oxidation of 2-hexanol with potassium dichromate?

A) hexene
B) hexanal
C) cyclohexane
D) hexanone

Question 60

Which of the following alkenes will be the major product when 2-methylcyclohexanol is heated with concentrated sulfuric acid?

A)
B)
C)
D)

Question 61

Which of the following is an example of a cyclic ether?

A) methoxycyclohexane
B) ethoxycyclopentane
C) tetrahydrofuran
D) ethrane

Question 62

Which of the following statements is true of dimethyl ether and ethanol?

A) The boiling points of dimethyl ether and ethanol are the same.
B) The boiling point of dimethyl ether is higher than the boiling point of ethanol.
C) The boiling point of dimethyl ether is lower than the boiling point of ethanol.
D) The boiling point of dimethyl ether is twice the boiling point of ethanol.

Question 63

Which of the following alcohols can be oxidized to ketones?

A) 1° alcohols
B) 2° alcohols
C) both 1° and 2° alcohols
D) both 2° and 3° alcohols

Question 64

Which of the following reagents was used in the original breath-alcohol screening test used by law enforcement officials?

A) Cr³⁺
B) hydrogen peroxide
C) potassium dichromate
D) acetic acid

Question 65

What is the smallest number of carbon atoms that can be found in an ether?

A) 1
B) 2
C) 3
D) 4

Question 66

By which of the following reaction sequences is ethanol converted to ethanoic acid?

A) successive oxidation
B) successive reduction
C) oxidation followed by reduction
D) reduction followed by oxidation

Question 67

Which of the following is obtained from the oxidation of sec-butyl alcohol with potassium dichromate in aqueous sulfuric acid?

A)
B)
C) both of these
D) neither of these

Question 68

Which of the given products can be obtained from the reaction of the following alcohol with sodium dichromate in aqueous sulfuric acid?

A)
B)
C)
D)

Question 69

What is the approximate C-O-C bond angle in the cyclic ether ethylene oxide, C₂H₄O?

A) 60°
B) 90°
C) 109°
D) 120°

Question 70

What is the smallest number of hydrogen atoms that can be found in a noncyclic ether?

A) 3
B) 6
C) 8
D) 10

Question 71

What is the common name of the following compound?

A) hexyl ether
B) propyl isopropyl ether
C) isopropyl propyl ether
D) dipropyl ether

Question 72

Which of the following alcohols can be oxidized to aldehydes in carefully controlled experimental conditions?

A) 1° alcohols
B) 2° alcohols
C) both 1° and 2° alcohols
D) both 2° and 3° alcohols

Question 73

What is the common name of the smallest cyclic ether?

A) ethylene oxide
B) methylene oxide
C) tetrahydrofuran
D) methoxycyclopentane

Question 74

What is the correct order of the boiling points of propane, dimethyl ether, and ethanol?

A) ethanol > dimethyl ether > propane
B) ethanol > propane > dimethyl ether
C) propane > dimethyl ether > ethanol
D) propane > ethanol > dimethyl ether

Question 75

Which of the following is the IUPAC name for the ether commonly called ethyl methyl ether?

A) ethoxymethane
B) ethoxyethane
C) methoxymethane
D) methoxyethane

Question 76

Which of the following is obtained from the oxidation of isobutyl alcohol with potassium dichromate in aqueous sulfuric acid?

A)
B)
C) both of these
D) neither of these

Question 77

Why are the boiling points of ethers similar to those of alkanes instead of alcohols?

A) Both ether molecules and alkane molecules are polar, whereas alcohol molecules are nonpolar.
B) Hydrogen bonding between ether molecules is strong and this property is similar to that of alkanes. However, hydrogen bonding is weaker in alcohols than it is in both ethers and alkanes.
C) Although ether molecules are polar, they cannot form hydrogen bonds with other ether molecules. Similarly, alkane molecules do not form hydrogen bonds, whereas there is hydrogen bonding in alcohols.
D) None of these are correct explanations.

Question 78

What is the smallest number of carbon atoms that can be found in an asymmetrical ether containing only C, H, and a single O atom?

A) 1
B) 2
C) 3
D) 4

Question 79

Which of the following reagents is used to convert menthol to menthone?

A) phosphoric acid alone
B) sulfuric acid alone
C) sodium hydroxide in the presence of water
D) potassium dichromate in the presence of sulfuric acid

Question 80

What is the approximate C-O-C bond angle in noncyclic ethers?

A) 90°
B) 109°
C) 120°
D) 180°