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Chapter 14

front 1

1) Compounds with the -OH group attached to a saturated alkane-like carbon are known as
A) alcohols.
B) alkyl halides.
C) ethers.
D) hydroxyls.
E) phenols.

back 1

Answer: A

front 2

2) Compounds with an oxygen atom bonded to two organic groups are known as
A) alcohols.
B) ethers.
C) hydroxides.
D) hydroxyls.
E) phenols.

back 2

Answer: B

front 3

3) None of the following organic compounds is very likely to form hydrogen bonds except
A) alkanes.
B) alkenes.
C) alcohols.
D) aromatics.
E) ethers

back 3

Answer: C

front 4

4) Alcohols, ethers, and phenols can be considered organic derivatives of the inorganic compound
A) ammonia.
B) carbon dioxide.
C) sodium hydroxide.
D) water.
E) none of these

back 4

Answer: D

front 5

5) Which molecule shown is an ether?

back 5

Answer: D

front 6

6) What is the inorganic compound that can be considered the structural basis for alcohols and ethers? Discuss two ways in which the physical properties of alcohols and ethers are similar to properties of this compound.

back 6

Answer: Alcohols and ethers can be considered to be derivatives of water. Similar physical properties include:
Polarity: Water is a very polar molecule; alcohols and ethers also display polarity.
Boiling point: Water has a higher boiling point than predicted on the basis of its molar mass. Alcohols also share this characteristic, but ethers do not.
Solubility: Water is miscible with other polar liquids; alcohols and ethers of low molar mass are miscible with water and with each other because of their polarity.

front 7

7) The alcohol which contains only one carbon atom and has the common name of wood alcohol is
A) ethanol.
B) glycerol.
C) glycol.
D) methanol.
E) phenol.

back 7

Answer: D

front 8

8) The common name of CH3OH is
A) grain alcohol.
B) wood alcohol.
C) rubbing alcohol.
D) antifreeze.
E) glycerol.

back 8

Answer: B

front 9

9) The alcohol which contains two carbon atoms and has the common name of grain alcohol is
A) ethanol.
B) glycerol.
C) glycol.
D) methanol.
E) phenol.

back 9

Answer: A

front 10

10) The common name of CH3CH2OH is
A) grain alcohol.
B) wood alcohol.
C) rubbing alcohol.
D) antifreeze.
E) glycerol.

back 10

Answer: A

front 11

11) The molecule with three carbon atoms with an -OH group on each, and used as a moisturizer is
A) ethanol.
B) glycerol.
C) glycol.
D) methanol.
E) phenol.

back 11

Answer: B

front 12

12) The common name of CH2(OH)CH2OH is
A) grain alcohol.
B) wood alcohol.
C) rubbing alcohol.
D) ethylene glycol (antifreeze).
E) glycerol.

back 12

Answer: D

front 13

13) Rubbing alcohol is a solution of
A) ethylene glycol.
B) glycerol.
C) isopropyl alcohol.
D) ethanol.
E) methanol.

back 13

Answer: C

front 14

14) Which of the following is commonly known as glycerol?

back 14

Answer: B

front 15

15) Which molecule shown is a glycol?

back 15

Answer: E

front 16

16) The common name of 1,2-ethanediol is
A) grain alcohol.
B) wood alcohol.
C) rubbing alcohol.
D) ethylene glycol (antifreeze)
E) glycerol.

back 16

Answer: D

front 17

17) The common name of CH3CH(OH)CH3 in water solution is
A) grain alcohol.
B) wood alcohol.
C) rubbing alcohol.
D) antifreeze.
E) glycerol

back 17

Answer: C

front 18

18) What is the IUPAC name of the compound shown?

A) 4-methyl-2-pentanol
B) 2-methyl-4-pentanol
C) 4,4-dimethyl-2-butanol
D) 2,2-dimethyl-4-butanol
E) 2-isohexanol

back 18

Answer: A

front 19

19) The IUPAC name of the alcohol shown is

A) 2,3-dimethyl-1-pentanol.
B) 2,3-dimethyl-5-pentanol.
C) 3,4-dimethyl-1-pentanol.
D) 3,4-dimethyl-5-pentanol.
E) primary 2,3-dimethylpentanol.

back 19

Answer: C

front 20

20) What is the IUPAC name of the compound shown?

A) 4-ethyl-1-hexanol
B) 3-ethyl-6-hexanol
C) 3-ethyl-1-hexanol
D) 4,4-diethyl-1-butanol
E) isooctanol

back 20

Answer: A

front 21

21) The name of the alcohol shown is

A) 2,4,4-trimethyl-3-pentanol.
B) 2,2,4-trimethyl-3-pentanol.
C) branched 3-octanol.
D) trimethyl-3-pentanol.
E) secondary 2,4,4-pentanol.

back 21

Answer: B

front 22

22) What is the systematic name for the following compound?

A) 2-methyl-3-pentanol
B) 2-methyl-3-pentenol
C) 4-methyl-3-pentanol
D) 3-methyl-2-pentanol

back 22

Answer: A

front 23

23) What is the IUPAC name of the compound shown?

A) butanetriol
B) 1,3,4-butanetriol
C) 1,2,4-butanetriol
D) 2-hydroxy-1,4-butanediol
E) butylene glycol

back 23

Answer: C

front 24

24) Compounds of the type R3C-OH are referred to as ________ alcohols.
A) primary
B) secondary
C) tertiary
D) quaternary
E) none of the above

back 24

Answer: C

front 25

25) Compounds of the type R2CH-OH are referred to as ________ alcohols.
A) primary
B) secondary
C) tertiary
D) quaternary
E) none of the above

back 25

Answer: B

front 26

26) Compounds of the type RCH2-OH are referred to as ________ alcohols.
A) primary
B) secondary
C) tertiary
D) quaternary
E) none of the above

back 26

Answer: A

front 27

27) Which compound is a tertiary alcohol?
A) 1-propanol
B) 2-methyl-1-hexanol
C) 2-methyl-2-hexanol
D) 3-methyl-2-hexanol
E) 3-hexanol

back 27

Answer: C

front 28

28) Which molecule shown is a primary alcohol?

back 28

Answer: C

front 29

29) The molecule shown is a ________ alcohol because ________.

A) primary; it has one -OH group
B) primary; its -OH group is on the end of the molecule
C) secondary; the carbon bonded to the -OH group is bonded to two other carbons
D) secondary; each group bonded to the hydroxyl carbon contains two carbon atoms
E) tertiary; the -OH is bonded to the number 3 carbon

back 29

Answer: C

front 30

30) Which molecule shown is a secondary alcohol?

back 30

Answer: A

front 31

31) An alcohol is classified as primary, secondary or tertiary based on
A) the number of carbon atoms bonded to the carbon bearing the OH group.
B) the number of carbon atoms in the molecule.
C) the number of hydrogens present in the alcohol.
D) the number of OH groups present in the molecule.
E) the mass of the alcohol

back 31

Answer: A

front 32

32) Which molecule shown is a tertiary alcohol?

back 32

Answer: B

front 33

33) How many isomeric alcohols exist with the formula C4H10O ?
A) 4
B) 1
C) 2
D) 3
E) 5

back 33

Answer: A

front 34

34) The relatively high boiling point of alcohols in relation to their molecular weights is the result of
A) covalent bonding.
B) dipolar forces.
C) hydrogen bonding.
D) ionic bonding.
E) London forces.

back 34

Answer: C

front 35

35) All of the following properties of alcohols are affected by hydrogen bonding except
A) boiling point.
B) miscibility with water.
C) ability to dissolve polar substances.
D) molecular weight.
E) none of the above

back 35

Answer: D

front 36

36) Which compound is the most soluble in water?
A) CH3CH2CH2CH2OH
B) CH3CH2CH2OH
C) CH3CH2CH2CH3
D) CH3CH2CH3
E) CH3CH2CH2CH2CH2CH2CH2CH3

back 36

Answer: B

front 37

37) Which compound is the least soluble in water?
A) CH3CH2CH2CH2OH
B) CH3CH2CH2OH
C) CH3CH2CH2CH3
D) CH3CH2CH3
E) CH3CH2CH2CH2CH2CH2CH2CH3

back 37

Answer: E

front 38

38) Which compound has the lowest boiling point?
A) CH3CH2CH2CH2CH2OH
B) CH3CH2CH2CH2CH3
C) CH3CH2CH2CH2OH
D) CH3CH2CH2CH3
E) CH3CH2CH2OH

back 38

Answer: D

front 39

39) Which of the following would at best be only very slightly soluble in water?
A) 1-hexanol
B) 2-propanol
C) 1,5-pentanediol
D) 1-propanol
E) 2-butanol

back 39

Answer: A

front 40

40) Which compound would have the highest boiling point?

back 40

Answer: B

front 41

41) Which compound has the highest boiling point?
A) CH3CH2CH2CH2CH2OH
B) CH3CH2CH2CH2CH3
C) CH3CH2CH2CH2OH
D) CH3CH2CH2CH3
E) CH3CH2CH2OH

back 41

Answer: A

front 42

42) Which of the following is the most soluble in water?
A) diethyl ether
B) methanol
C) 1-butanol
D) 1-decanol
E) decane

back 42

Answer: B

front 43

43) Which of the following is the most soluble in water?
A) HOCH2CH2CH2OH
B) CH3CH2CH2CH2OH
C) CH3CH2OCH2CH3
D) CH3CH2CH2CH3
E) CH3CH2CH2OCH3

back 43

Answer: A

front 44

44) Which of the following would be the least soluble in water?
A) HOCH2CH2CH2OH
B) CH3CH2CH2CH2OH
C) CH3CH2OCH2CH3
D) CH3CH2CH2CH3
E) CH3CH2CH2OCH3

back 44

Answer: D

front 45

45) Which compound has the lowest boiling point?
A) CH3CH2CH2CH2OH
B) CH3CH2CH2OH
C) CH3CH2OCH2CH3
D) CH3CH2OCH3
E) CH3CH2CH2OCH3

back 45

Answer: D

front 46

46) Which compound has the highest boiling point?
A) CH3CH2CH2CH2OH
B) CH3CH2CH2OH
C) CH3CH2OCH2CH3
D) CH3CH2OCH3
E) CH3CH2CH2OCH3

back 46

Answer: A

front 47

47) Which compound would you expect to have the lowest boiling point?
A) methane
B) methanol
C) dimethyl ether
D) ethanol
E) water

back 47

Answer: A

front 48

48) Which alcohol is most soluble in water?
A) ethanol
B) 1-propanol
C) 1-butanol
D) 1-pentanol
E) 1-hexanol

back 48

Answer: A

front 49

49) Describe and explain the change in water solubility of straight-chain primary alcohols as molar mass increases.

back 49

Answer: As the molar mass of these alcohols increases, the water solubility decreases. This occurs because the polarity of the hydroxyl group, which is the reason for the interaction with the polar water molecules, becomes less important as the size of the nonpolar hydrocarbon portion of the molecule increases.

front 50

50) The product of dehydration of an alcohol is an

A) alkane.
B) alkene.
C) aromatic.
D) ether.
E) aldehyde.

back 50

Answer: B

front 51

51) Oxidation of an alcohol group results in formation of a(an) ________ group.
A) alkyl
B) aromatic
C) carbonyl
D) ether
E) hydroxyl

back 51

Answer: C

front 52

52) The symbol [O] written above a reaction arrow means
A) oxygen is removed from one of the reactants during the reaction.
B) the reaction consumes oxygen from the atmosphere.
C) that an oxidation reaction is occurring.
D) that a reduction reaction is occurring and oxygen is liberated.
E) none of the above

back 52

Answer: C

front 53

53) Oxidation of R2CHOH will produce
A) an aldehyde.
B) a ketone.
C) an alkene.
D) a carboxylic acid.
E) no reaction.

back 53

Answer: B

front 54

54) Oxidation of a tertiary alcohol will produce
A) an aldehyde.
B) a ketone.
C) an alkene.
D) a carboxylic acid.
E) no reaction.

back 54

Answer: E

front 55

55) Treatment of CH3CH2CH2OH with a limited amount of oxidizing agent will produce
A) an aldehyde.
B) a ketone.
C) an alkene.
D) a carboxylic acid.
E) no reaction

back 55

Answer: A

front 56

56) Treatment of CH3CH2OH with an excess amount of oxidizing agent will produce
A) an aldehyde.
B) a ketone.
C) an alkene.
D) a carboxylic acid.
E) no reaction.

back 56

Answer: D

front 57

57) Gentle oxidation of a primary alcohol will produce
A) an aldehyde.
B) an alkene.
C) a carboxylic acid.
D) an ether.
E) a ketone.

back 57

Answer: A

front 58

58) Gentle oxidation of a secondary alcohol will produce
A) an aldehyde.
B) an alkene.
C) a carboxylic acid.
D) an ether.
E) a ketone.

back 58

Answer: E

front 59

59) Strong oxidation of a primary alcohol will produce

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

back 59

Answer: C

front 60

60) Which of the following would be the product of the oxidation of 2-methyl-3-pentanol?

back 60

Answer: B

front 61

61) Treatment of the molecule shown with a strong oxidizing agent will produce

A) an aldehyde.
B) an alkene.
C) a carboxylic acid.
D) a ketone.
E) no reaction.

back 61

Answer: E

front 62

62) Which of the following alcohols would not be able to be oxidized with any type of oxidizing agent?

back 62

Answer: C

front 63

63) Treatment of the molecule shown with a dehydrating agent will produce

A) an aldehyde.
B) an alkene.
C) a carboxylic acid.
D) a ketone.
E) no reaction.

back 63

Answer: B

front 64

64) The major product obtained from dehydration of 2-hexanol is
A) 1-hexene.
B) 2-hexene.
C) 3-hexene.
D) 2-hexanone.
E) 2-hexanal

back 64

Answer: B

front 65

65) Which alcohol should be used to produce 2-methyl-3-pentene by dehydration?
A) 2-methyl-3-pentanol
B) 4-methyl-2-pentanol
C) 4-methyl-1-pentanol
D) 2-methyl-1-pentanol
E) 1-propanol and 2-propanol

back 65

Answer: B

front 66

66) The major product resulting from the dehydration of

A) 1-pentene.
B) 2-pentene.
C) n-pentane.
D) 1,2-pentanediol.
E) 1,3-pentanediol.

back 66

Answer: B

front 67

67) Which of the following is the major product formed from dehydration of the following alcohol?

back 67

Answer: C

front 68

68) What is the product of the oxidation of a secondary alcohol?
A) ketone
B) aldehyde
C) alkene
D) carboxylic acid
E) alkyne

back 68

Answer: A

front 69

69) Oxidation reactions are defined differently in organic chemistry than they are in inorganic chemistry. Give the definition of both and explain their similarities.

back 69

Answer: The inorganic definition of oxidation is loss of electrons. The organic definition is formation of additional bonds between carbon and oxygen (or a decrease in the number of carbon-hydrogen bonds). These are similar because when carbon forms a bond with electronegative oxygen, it essentially loses some of its attraction for its electrons.

front 70

70) The simplest aromatic alcohol, recognized by its strong medicinal odor and used as a disinfectant is
A) ethanol.
B) glycerol.
C) glycol.
D) methanol.
E) phenol.

back 70

Answer: E

front 71

71) Which compound is sometimes called carbolic acid?
A) ethanol
B) methanol
C) glycerol
D) ether
E) phenol

back 71

Answer: E

front 72

72) Compounds with the -OH group attached to an aromatic ring are known as
A) alcohols.
B) alkyl halides.
C) ethers.
D) hydroxyls.
E) phenols.

back 72

Answer: E

front 73

73) Which molecule would be considered a derivative of phenol?

back 73

Answer: C

front 74

74) Which molecule would be the most acidic?
A) dimethyl ether
B) ethanol
C) phenol
D) water
E) 1-hexanol

back 74

Answer: C

front 75

75) When phenol acts as an acid, a ________ ion is produced.
A) phenyl
B) benzyl
C) phenolate
D) phenolic
E) phenoxide

back 75

Answer: E

front 76

76) The molecule CH3CH2CH2OCH2CH3 can be classified as
A) an alcohol.
B) an aldehyde.
C) an alkane.
D) an ether.
E) a ketone

back 76

Answer: D

front 77

77) All of the following are properties of ethers except
A) the molecules are polar, but do not form hydrogen bonds with other ether molecules.
B) low molecular weight ethers are flammable and evaporate easily.
C) ethers dissolve readily in water in all proportions.
D) ethers are relatively unreactive except for flammability.
E) ethers dissolve many organic compounds readily.

back 77

Answer: C

front 78

78) What is the IUPAC name of the compound shown?

CH3CH2CH2OCH3

A) 1,2-etherbutane
B) methyl propyl ether
C) propyl methyl ether
D) butyl ether
E) isobutyl ether

back 78

Answer: B

front 79

79) Ether molecules are polar, but do not form hydrogen bonds with other ether molecules because
A) the molecules are generally too large.
B) there is no hydrogen atom bonded to the oxygen.
C) there are too many hydrogen atoms on the molecules to bond with just one oxygen atom.
D) only binary compounds form hydrogen bonds.
E) ether molecules are so reactive that they never have an opportunity to form hydrogen bonds.

back 79

Answer: B

front 80

80) What is the systematic name of the following compound?

A) 2-methoxy propane
B) 2-ethoxy propane
C) ethyl methyl ether
D) diethyl ether

back 80

Answer: A

front 81

81) Organic compounds which are sulfur analogs of alcohols are referred to as

A) sulfuric alcohols.
B) disulfides
C) halides.
D) thiols.
E) carbonyls

back 81

Answer: D

front 82

82) Which property of thiols makes them useful as additives to natural gas?
A) flammability
B) solubility
C) odor
D) color
E) disinfectant

back 82

Answer: C

front 83

83) The reaction conditions which would result in formation of disulfides from thiols are
A) mild oxidizing.
B) gentle heat.
C) strong heat.
D) strong acid.
E) none of these

back 83

Answer: A

front 84

84) What is the IUPAC name of the compound shown?

A) 2-thiobutane
B) 3-thiobutanol
C) 2-butanethiol
D) 1-methyl-1-thiopropane
E) 1-methyl-1-propanethiol

back 84

Answer: C

front 85

85) When a thiol is oxidized the product is
A) an aldehyde.
B) a ketone.
C) sulfuric acid.
D) a disulfide.
E) an alkene

back 85

Answer: D

front 86

86) The most characteristic feature of thiols is ________
A) odor
B) solubility in water
C) reactivity with water
D) boiling point
E) color

back 86

Answer: A

front 87

87) What is the IUPAC name of the compound shown?

A) di(chloroethane)
B) 2,3-dichlorobutane
C) 1,2-dichloro-1,2-dimethylethane
D) 1,2-dichloro-1-methylpropane
E) 2,3-dichlorbutane

back 87

Answer: B

front 88

88) What is the IUPAC name for the compound shown?

A) 3-bromo-2-chloro-3-methylpentane
B) 3-bromomethyl-2-chloro-pentane
C) bromochlorohexane
D) 3-bromo-4-chloro-3-methylpentane
E) none of these

back 88

Answer: A

front 89

89) Give the IUPAC name for the following compound:

A) 1,2-dibromo-1-methyl butane
B) 2,3-dibromopentane
C) 3,4-dibromopentane
D) 2,3-bromopentane

back 89

Answer: B

front 90

90) All of the following can be classified as alkyl halides except
A) styrene, the monomer used to make foam coffee cups.
B) chloroform, an anesthetic.
C) iodoform, an disinfectant
D) methyl bromide, an insecticide.
E) CFC's used as refrigerants

back 90

Answer: A