Deck 14: 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

What are the approximate bond angles at the OH-bearing carbon atom of all alcohols?

A) 90°
B) 109°
C) 120°
D) 180°

Answer 3

B

Question 4

Which of the following elements is present in thiols but not in alcohols?

A) C
B) O
C) P
D) S

Question 5

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 6

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 7

Which of the following is a complete and correct IUPAC name?

A) 1-isopropyl-3-cyclohexanol
B) 3-isopropyl-1-cyclohexanol
C) 3-isopropylcyclohexanol
D) cis-3-isopropylcyclohexanol

Question 8

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

A)
B)
C)
D)

Question 9

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 10

What is the geometry at the OH-bearing carbon atom of all alcohols?

A) linear
B) tetrahedral
C) trigonal planar
D) none of these

Question 11

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 12

Which of the following is a glycol?

A) HOCH₂CH₂CH₂OH
B)
C) HOCH₂CH₂OH
D) None of these is a glycol.

Question 13

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 14

Which of the following is(are) glycols?

A) HOCH₂CH₂CH₂CH₂CH₂OH
B)
C) both a and b
D) neither a nor b

Question 15

Which of the following structures represents 4-methylcyclohexanol?

A)
B)
C)
D)

Question 16

Which of the following compounds has an extremely disagreeable odor?

A) CH₃CH₂OH
B) CH₃CH₂OCH₂CH₃
C) CH₃CH₂SH
D) none of these

Question 17

Which of the following is a correct IUPAC name?

A) 1-isopropyl-1-cyclohexanol
B) 1-isopropylcyclohexanol
C) trans-1-isopropyl-1-cyclohexanol
D) none of these

Question 18

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 19

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 20

Which of the following is the common name of 2-methyl-2-propanol?

A) sec-butyl alcohol
B) tert-butyl alcohol
C) isobutyl alcohol
D) isopropyl alcohol

Question 21

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

A) One is primary and one is secondary.
B) One is primary and one is tertiary.
C) Both are primary.
D) Neither is primary.

Question 22

Which of the following alcohols has the lowest boiling point?

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

Question 23

Of the alcohols with the molecular formula C₄H₉OH, which has the highest boiling point?

A) 1-butanol
B) sec-butyl alcohol
C) tert-butyl alcohol
D) isobutyl alcohol

Question 24

What is the color of pure ethylene glycol?

A) colorless
B) green
C) red
D) white

Question 25

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 26

Which of the following is true about the polarities of the C−O and O−H bonds?

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 27

Given that in stable diols the two hydroxyl groups are not attached to the same carbon atom, which of the following is the molecular formula of a stable diol in which both alcohol functional groups are tertiary?

A) C₃H₈O₂
B) C₄H₁₀O₂
C) C₅H₁₂O₂
D) C₆H₁₄O₂

Question 28

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

A) One is secondary and one is tertiary.
B) Both are secondary.
C) Both are tertiary.
D) None of the above is true.

Question 29

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 30

Which of the following alcohols is most soluble in water?

A) 1-pentanol
B) 1,5-pentanediol
C) 1,3,5-pentanetriol
D) None, they are all equally soluble.

Question 31

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

A) One is primary and one is secondary.
B) One is primary and one is tertiary.
C) Both are primary.
D) Neither is primary.

Question 32

Of the alcohols with the molecular formula C₄H₉OH, which has the lowest boiling point?

A) 1-butanol
B) sec-butyl alcohol
C) tert-butyl alcohol
D) isobutyl alcohol

Question 33

What is the maximum number of hydrogen bonds which can be formed by a single molecule of an alcohol which contains only one hydroxyl group?

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

Question 34

Which of the following compounds is most soluble in water?

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

Question 35

Which of the following alcohols is least soluble in water?

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

Question 36

Which of the following statements about London dispersion forces is/are true?

A) London dispersion forces are stronger between molecules of 1-butanol than between molecules of 2-methyl-2-propanol.
B) London dispersion forces are weaker than hydrogen bonding interactions.
C) both a and b
D) neither a nor b

Question 37

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

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

Question 38

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

A) One is primary and one is secondary.
B) One is primary and one is tertiary.
C) Both are primary.
D) Neither is primary.

Question 39

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

A) 1° alcohols
B) phenols
C) both a and b
D) neither a nor b

Question 40

Which of the following statements concerning the boiling points of isomeric alcohols is true?

A) Isomeric alcohols have the same boiling points.
B) The relative boiling points of isomeric alcohols are determined primarily by the different number of hydrogen bonds which they can form.
C)
C) The relative boiling points of isomeric alcohols are determined primarily by the different shapes of the molecules.
D) The relative boiling points of isomeric alcohols are determined equally by both b and

Question 41

Which of these responses describes the products formed by heating the following 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 major product is 2-methyl-2-hexene and the minor product is 2-methyl-1-hexene.

Question 42

Which of the following 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) none of these

Question 43

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

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

Question 44

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

A)
B)
C)
D)

Question 45

Which of the alcohols shown below will react when heated with concentrated sulfuric acid to give the following alkene as the major product?

A)
B)
C) both a and b
D) neither a nor b

Question 46

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

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

Question 47

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 48

Which definition of oxidation is most useful when considering the oxidation of tertiary alcohols?

A) gain of oxygen
B) loss of electrons
C) loss of hydrogen
D) None of these, 3° alcohols are not oxidized.

Question 49

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

A) 2,2,4,4-tetramethyl-2-pentene is the only product.
B) 2,2,4,4-tetramethyl-3-pentene is the only product.
C) 2,2,4,4-tetramethyl-4-pentene is the only product.
D) There is no product, since 2,2,4,4-tetramethyl-3-pentanol does not undergo dehydration.

Question 50

Suppose you carried out two reactions in sequence. In the first reaction you hydrated 1-hexene and 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) none of the above

Question 51

Of 1-pentanol, 2-pentanol and 3-pentanol, which compound(s) can yield only a single alkene product when dehydrated?

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

Question 52

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 53

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

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

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

Which of the following is true of the hydration-dehydration equilibrium which 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 56

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

A) The only product is 1-methylcyclopentene.
B) The only product 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 57

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

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

Question 58

Which of the following describes the products formed by the dehydration of trans-4-methylcyclohexanol?

A) The only product is 4-methylcyclohexene.
B) The only product 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 59

When a primary alcohol is oxidized to a carboxylic acid, an intermediate product is an aldehyde. Which physical property of the aldehyde can be exploited if it is desired to obtain the aldehyde as the reaction product?

A) boiling point
B) molecular weight
C) solubility
D) any of these

Question 60

Which definition of oxidation is most useful when considering the oxidation of primary or secondary alcohols?

A) gain of oxygen
B) loss of electrons
C) loss of hydrogen
D) None of these, 1° and 2° alcohols are not oxidized.

Question 61

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

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

Question 62

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

A) Cr³⁺
B) hydrogen peroxide
C) potassium dichromate
D) none of these

Question 63

Which of the following is obtainable by the oxidation of tert-butyl alcohol?

A)
B)
C) both a and b
D) neither a nor b

Question 64

Which of the following correctly gives the order of boiling points for the molecules 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 65

What is the smallest number of hydrogen atoms which can be found in a noncyclic unsymmetrical ether that contains only C, H and a single O atom?

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

Question 66

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 67

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

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

Question 68

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

A)
B)
C) both a and b
D) neither a nor b

Question 69

Ketones can be obtained by the oxidation of which of the following?

A) 1° alcohols
B) 2° alcohols
C) 3° alcohols
D) none of these

Question 70

What color change is associated with the original breath alcohol test?

A) green to reddish orange
B) reddish orange to green
C) colorless to pink
D) None, the test is not based on a color change.

Question 71

If experimental conditions are carefully controlled, aldehydes can be obtained by the oxidation of which of the following?

A) 1° alcohols
B) 2° alcohols
C) 3° alcohols
D) all of these

Question 72

Which of the following is the name of the smallest cyclic ether?

A) ethylene oxide
B) methylene oxide
C) tetrahydrofuran
D) none of these

Question 73

What is the common name for the following compound?

A) hexyl ether
B) propyl isopropyl ether
C) isopropyl propyl ether
D) none of these

Question 74

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

A)
B)
C)
D)

Question 75

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

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

Question 76

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

A) 90°
B) 109°
C) 120°
D) 180°

Question 77

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

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

Question 78

Which of the following explains why the boiling points of ethers are more similar to those of comparable alkanes than to those of comparable alcohols?

A) Both ether molecules and alkane molecules are nonpolar.
B) Hydrogen bonding between ether molecules is weak.
C) Although ether molecules are polar they cannot form hydrogen bonds to other ether molecules.
D) None of the above is the correct explanation.

Question 79

What is the name of the −OCH₃ group?

A) methyloxy
B) methoxy
C) oxymethyl
D) oxymeth

Question 80

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

A)
B)
C) both a and b
D) neither a nor b