Ch14 Organic Compounds That Contain Oxygen, Test Bank Docx

General, Organic and Biological Chemistry, 4e (Smith)

Chapter 14 Organic Compounds That Contain Oxygen, Halogen, or Sulfur

1) What is the functional group in thiols?

A) Sulfide group

B) Sulfate group

C) Sulfhydryl group

D) Sulfite group

2) Which is a secondary alcohol?

A)

B)

C)

D)

E) More than one of the compounds is a secondary alcohol.

3) Which is a primary alcohol?

A)

B)

C)

D)

4) Which is a primary alcohol?

A)

B)

C) CH3CH2CH2OH

D)

5) The molecule below is classified as what type of alcohol?

A) Secondary alcohol

B) Primary alcohol

C) Tertiary alcohol

6) The molecule below is classified as what type of alcohol?

A) Secondary alcohol

B) Primary alcohol

C) Tertiary alcohol

7) What is the shape around the oxygen atom in an alcohol?

A) Tetrahedral

B) Trigonal pyramidal

C) Trigonal planar

D) Bent

E) Linear

8) Which alcohol is most soluble in water?

A) (CH3)2CHCH2OH

B) CH3CH2CH2CH2CH2CH2CH2OH

C) CH3(CH2)10CH2OH

D) All alcohols are soluble in water.

9) What is the IUPAC name of the compound below?

A) 2,2-dimethyl-3-propanol

B) 2,2-dimethyl-1-propanol

C) 3,3-dimethyl-1-butanol

D) 2,2-dimethyl-4-butanol

10) What is the IUPAC name of the compound below?

A) 2-propyl-2-butanol

B) 2-methy-4-heptanol

C) 2-ethyl-2-pentanol

D) 3-methyl-3-hexanol

11) What is the IUPAC name of the compound below?

A) 1-pentanol

B) Phenol

C) Cyclo-1-pentol

D) Cyclopentanol

12) What is the structure of 1-chloro-3-ethyl-2-heptanol?

A)

B)

C)

D)

13) What is the structure of 3-methyl-4-propyl-3-octanol?

A)

B)

C)

D)

14) What is the major product of the dehydration of the compound below?

A)

B)

C)

D)

15) How many products, including stereoisomers, are possible from the dehydration of the alcohol below?

A) 1

B) 2

C) 3

D) 4

16) How many products are possible from the dehydration of the alcohol below?

A) 1

B) 2

C) 3

D) 4

17) What reagent is commonly used for alcohol dehydration?

A) K2Cr2O7

B) H2SO4

C) Cl2

D) H2O

18) What is/are the carbonyl product(s) formed when the alcohol below is oxidized with K2Cr2O7?

A) CH3(CH2)4COOH

B)

C)

D)

then

E) No reaction occurs.

19) What is/are the carbonyl product(s) formed when the alcohol below is oxidized with K2Cr2O7?

A)

B)

C)

D)

then

E) No reaction occurs.

20) What alcohol would be oxidized to form the compound below?

A) CH3(CH2)5CH2OH

B)

C)

D)

21) Which is an example of an ether?

A)

B)

C)

D)

E) None of these structures is an ether.

22) What type of product results from the reaction shown below?

A) A cyclic carboxylic acid

B) A primary alcohol

C) A cyclic ketone

D) An ether

23) Which compound has the highest boiling point?

A) CH3(CH2)4CH2OH

B) CH3(CH2)2O(CH2)2CH3

C) CH3(CH2)5CH3

D) All of the compounds have the same boiling point.

24) What is the common name of CH3(CH2)2–O–(CH2)2CH3?

A) Propyl propyl ether

B) Dipropyl ether

C) Dibutyl ether

D) Butyl butyl ether

E) Butyl propyl ether

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

A) Heptyl methyl pentyl ether

B) Nonyl pentyl ether

C) 8-pentoxynonane

D) 2-nonyl pentyl ether

E) 2-pentoxynonane

26) What is the structure of methoxycyclobutane?

A)

B)

C)

D)

27) Which compound has the lowest boiling point?

A)

B)

C)

D)

E)

28) Which compound has the lowest boiling point?

A) BrCH2CH2CH2CH3

B) FCH2CH2CH2CH2CH3

C) FCH2CH2CH2CH3

D) ClCH2CH2CH2CH2CH3

E) ICH2CH2CH2CH2CH3

29) Which compound has the highest boiling point?

A) CH3CH2CH2Cl

B) CH3CH2CH2OH

C) CH3CH2CH2F

D) CH3CH2CH2Br

E) CH3CH2CH3

30) Which compound has the highest boiling point?

A) BrCH2CH2CH2CH3

B) FCH2CH2CH2CH2CH3

C) FCH2CH2CH2CH3

D) ClCH2CH2CH2CH2CH3

E) ICH2CH2CH2CH2CH3

31) What is the common name of the compound below?

A) Pentyl iodide

B) 5-iodopentane

C) Hexyl iodide

D) Iodyl pentane

32) What is the common name of the compound below?

CH3CH2CH2CH2Br

A) 1-bromobutane

B) Butyl bromide

C) Pentyl bromide

D) Propyl bromide

33) What is the structure of 1,1,2-trichloroethane?

A)

B)

C)

D) More than one of the structures is 1,1,2-trichloroethane.

34) What is the structure of 1,2,4-trifluorocyclopentane?

A)

B)

C)

D)

35) Which statement concerning chlorofluorocarbons (CFCs) is not true?

A) CFCs are simple halogen-containing compounds having the general molecular formula CFxCl4 – x.

B) CFCs are manufactured under the trade name Freons.

C) CFCs are inert and nontoxic.

D) CFCs are currently used as refrigerants, solvents, and aerosol propellants in the United States.

E) CFCs are decomposed by sunlight, forming highly reactive intermediates that have been shown to destroy the ozone layer.

36) What is the IUPAC name of the compound below?

A) 3,6-diethyl-3-methyl-8-decathiol

B) 3,6-diethyl-3-methyl-8-decanethiol

C) 5,8-diethyl-8-methyl-5-decanethiol

D) 5,8-diethyl-8-methyl-5-decathiol

E) 3-butyl-6-ethyl-6-methyl-3-octanethiol

37) Which compound has the lowest boiling point?

A) CH3(CH2)4CH2OH

B) CH3(CH2)4CH3

C) CH3(CH2)4CH2SH

D) CH3(CH2)4CH2OH and CH3(CH2)4CH2SH have the same boiling point and the boiling point is lower than that of CH3(CH2)4CH3.

38) What product is formed when CH3CH2CH2CH2–SH is oxidized?

A)

B) CH3CH2CH2CH2–S–S–CH2CH2CH2CH3

C)

D) CH3CH2CH2CH2–S–CH2CH2CH2CH3

39) Which alcohol can be dehydrated with sulfuric acid to form the alkene below?

A)

B)

C)

D) Dehydration of more than one of the compounds produces the desired product.

40) Which compound is a secondary alkyl halide?

A)

B)

C)

D)

E) More than one of the compounds is a secondary alkyl halide.

41) Which compound is a secondary alkyl halide?

A)

B)

C)

D)

E) More than one of the compounds is a secondary alkyl halide.

42) What product forms when the following disulfide is reduced?

A)

B)

C)

D)

43) Which compound can be oxidized to a carboxylic acid?

A)

B)

C)

D)

44) Which compound can be oxidized to a carboxylic acid?

A)

B)

C)

D)

45) Which compound is a glycol?

A)

B)

C)

D)

46) Which compound is a glycol?

A)

B)

C)

D)

47) What is the IUPAC name of the compound below?

A) 2,6-dihydroxytoluene

B) 1-methyl-2,6-cyclohexanediol

C) 2-methyl-1,3-cyclohexanediol

D) 2-methyl-3-hydroxyphenol

48) Which statement concerning the compound shown below is incorrect?

A) It is a tertiary alcohol.

B) Its molecular formula is C6H14O.

C) Its name is 2-methyl-2-pentanol.

D) It can be oxidized to give a ketone.

49) Which statement concerning the compound shown below is incorrect?

A) It is a secondary alcohol.

B) Its molecular formula is C6H12O.

C) Its name is phenol.

D) It can be oxidized to give a ketone.

50) What dithiol is formed when the cyclic disulfide shown below is reduced?

A)

B)

C)

D)

51) What products are formed when the disulfide shown below is reduced?

A)

B)

C)

D)

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

A)

B)

C)

D)

53) Benzyl alcohol is a colorless liquid with a gentle, pleasant aroma.  What is the first product formed when benzyl alcohol is oxidized?

A)

B)

C)

D)

54) Alcohol dehydration reactions are important biological reactions. For example, 2-phosphogylcerate undergoes dehydration in the glycolysis pathway to produce phosphoenolpyruvate. Which structure represents the product that results when 2-phosphoglycerate is dehydrated?

A)

B)

C)

D)

55) Which structure represents the product that results when the given structure is dehydrated with H2SO4?

A)

B)

C)

D)

56) Which statement best describes the changes that occurred in the reactant in forming the alkene product?

A) An H atom and an OH group have been removed from the reactant.

B) The OH group was removed from the reactant.

C) The OH group was replaced by an H atom.

D) Two H atoms were removed from the reactant.

57) Primary (1°) alcohols are first oxidized to aldehydes (RCHO), which are further oxidized to carboxylic acids (RCOOH).

58) Secondary (2°) alcohols are first oxidized to aldehydes (RCHO), which are further oxidized to ketones (RCOR).

59) The oxidation of CH3CH2OH with K2Cr2O7 was the first method used for the routine testing of alcohol concentration in exhaled air.

60) When ethanol (CH3CH2OH) is ingested, it is oxidized in the liver first to acetaldehyde by alcohol dehydrogenase, and then to acetic acid by aldehyde dehydrogenase.

61) Antabuse, a drug given to alcoholics to prevent them from consuming alcoholic beverages, acts by interfering with the normal oxidation of ethanol. Antabuse inhibits the oxidation of ethanol to acetaldehyde.

62) Ethers are organic compounds that have two alkyl groups bonded to an oxygen atom.

63) Ethers have stronger intermolecular forces than alkanes but weaker intermolecular forces than alcohols.

64) Cyclopentanol has a higher boiling point than methylcyclopentane.

65) The compound below is expected to be soluble in water.

66) The compound below is expected to be soluble in water.

67) The compound below is a secondary alkyl halide.

68) Propyl bromide is a primary alkyl halide.

69) Alkyl halides are soluble in water when the alkyl group has less than five carbons.

70) CH3CH2CH2CH2Cl has a higher melting point than CH3CH2CH2CH2Br.

71) Thiols have higher boiling points and melting points than alcohols having the same size and shape.

72) CHCl2F is classified as a CFC.

73) Thiols are oxidized to sulfates.

74) CH3CH2CH2CH2–S–S–CH2CH2CH3 is an example of a disulfide compound.

75) In the simple sugar D-glucose (structure shown), there are two primary –OH groups.

76) The alcohol shown below can be oxidized with K2Cr2O7 to give the indicated product.

77) The alcohol shown below can be oxidized with K2Cr2O7 to give the indicated product.

78) Two ether molecules can form hydrogen bonds with each other.

79) The two alcohols below are dehydrated with H2SO4 to give the same major product.

80) The IUPAC name of the compound below is 2-pentanol.

81) Including stereoisomers, there are two possible products when the compound below is dehydrated with H2SO4.

82) The IUPAC name of the compound below is 5-ethyl-5-methyl-7-nonanethiol.

83) The IUPAC name of the compound below is 1-ethyl-3-cyclopentanethiol.

84) The IUPAC name of the compound below is 3-methyl-3-hexanethiol.

85) Thiols have pleasant, sweet odors.

86) To make straight hair curly, the disulfide bonds holding the protein chains together are reduced, forming free SH groups. The hair is turned around curlers and then an oxidizing agent is applied that reforms the disulfide bonds to the hair, giving it a curly appearance.

87) The alkene product in the dehydration reaction below is the one predicted by the Zaitsev rule.

88) The compound below will not be oxidized by K2Cr2O7.

89) Vitamin D4 (structure shown) can be oxidized by K2Cr2O7 to give a ketone.

90) Vitamin D4 (structure shown) can be oxidized by K2Cr2O7 to give a ketone.

91) Dehydration of an alcohol yields an alkene product.

92) Ethers are the class of compounds primarily responsible for the foul smell of skunk spray.

93) Cortisol, an anti-inflammatory agent, contains a primary alcohol, a secondary alcohol, and a tertiary alcohol.

94) Glucose, a common monosaccharide shown below, contains a primary alcohol, a secondary alcohol, and a tertiary alcohol.

95) The compound below may be classified as an alkene, ether, and an alcohol.

96) The compound below may be classified as aromatic, an ether, and an amine.

97) A thiol is a sulfur analogue of an alcohol, formed by replacing the oxygen by sulfur.

98) Every –OH group in an organic molecule is an alcohol functional group.

99) Starch and cellulose are two polymers that contain many –OH groups and belong to the family of molecules called carbohydrates.

100) Ethylene glycol (HOCH2CH2OH), a diol, is the major component of antifreeze.

101) According to the Zaitsev rule, the major product in an elimination reaction from an alcohol is the alkene that has fewer alkyl groups bonded to it.

102) Alcohols undergo two useful reactions: ________ and ________.

103) When the ether functional group is part of a three-membered ring, the ether is called a(n) ________.

104) A thiol is converted to a disulfide in a(n) ________ reaction.

105) The Zaitsev rule is used to predict the major product of a(n) ________ reaction of alcohols.

106) Ethers have a ________ shape around the oxygen atom and two polar C–O bonds, so they (have/do not have) ________ a net dipole.

107) Secondary alcohols (R2CHOH) are oxidized to ________.

108) A student incorrectly names a compound as 2,6-diethyl-2-propyl-5-heptanethiol. The correct IUPAC name of this compound is ________.

109) The IUPAC name of the compound below is ________.

110) The IUPAC name of the compound below is ________.

111) The compound shown below contains ________ ether functional groups.

112) The IUPAC name of the structure below is ________.