Organic Chemistry Complete Test Bank Chapter 16

Introduction to Chemistry, 5e (Bauer)

Chapter 16 Organic Chemistry

1) Which of the following molecules has only single bonds?

A) CHCHCH3

B) CH2CHCH3

C) CH3CH2CCH

D) CH3CH3

E) CH2CH2

2) Which of the following molecules has only single bonds?

A) CH3CHCH2

B) CH3CH2CH3

C) CH2CHCH2CH3

D) CHCH

E) CH3CCH

3) Which of the following molecules has a carbon-to-carbon double bond?

A) CH3CCH

B) CHCH

C) CH3CH3

D) CH3CH2CH3

E) CH2CHCH3

4) Which of the following molecules has a carbon-to-carbon triple bond?

A) CH3CH3

B) CH2CHCH3

C) CH3CCH

D) CH3CH2CH3

E) CH2CHCH2CH3

5) List the number and type of bonds in the compound CH2CHCH2CH3.

A) 12 single bonds

B) 11 single bonds, and 1 double bond

C) 10 single bonds, and 1 double bond

D) 11 single bonds

E) 13 single bonds

6) List the number and type of bonds in the molecule CH3CCCH3.

A) 7 single bonds, and 2 double bonds

B) 6 single bonds, and 3 double bonds

C) 9 single bonds

D) 8 single bonds, and 1 double bond

E) 8 single bonds, and 1 triple bond

7) To which class of compounds does the molecule CH3CH2NH2 belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) carboxylic acid

8) To which class of compounds does the compound shown belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) aromatic compound

9) To which class of compounds does the molecule CH3CH2OH belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) carboxylic acid

10) To which class of compounds does the molecule CH3CH=CH2 belong?

A) alkane

B) aldehyde

C) alcohol

D) alkene

E) carboxylic acid

11) To which class of compounds does the molecule shown in the figure belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) carboxylic acid

12) To which class of compounds does the compound shown in the figure belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) carboxylic acid

13) To which class of compounds does the compound shown in the figure belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) carboxylic acid

14) To which class of compounds does the molecule CH3CH2CO2H belong?

A) ketone

B) aldehyde

C) alcohol

D) carboxylic acid

15) To which class of compounds does the molecule shown in the figure belong?

A) ketone

B) aldehyde

C) alcohol

D) amine

E) carboxylic acid

16) To which class of compounds does the molecule CH3CH2OCH3 belong?

A) ketone

B) aldehyde

C) alcohol

D) ether

E) carboxylic acid

17) To which class of compounds does the molecule shown in the figure belong?

A) ketone

B) aldehyde

C) alcohol

D) ester

E) carboxylic acid

18) Which of the following is the structural formula for the molecule represented in the figure?

A) CH3CH2CH2CH2CH3

B) CH3CH2CH3

C) CH2CH2CH2CH2CH2

D) CH2CHCHCHCH2

E) CHCHCHCHCH

19) Which of the following is the molecular formula for the molecule represented in the figure?

A) C6H6

B) C6H8

C) C6H10

D) C6H12

E) C6H16

20) Which of the following is the molecular formula for the molecule represented in the figure?

A) C7H15O

B) C7H13O

C) C6H10O

D) C6H12O

E) C6H6O

21) The condensed structural formula for the molecule shown in the figure is ________.

A) C8H14O

B) CH3CH2CH(CH3)COCH2CH3

C) CH3CH2CH(CH3)2COCH2CH3

D) CH3CH2CH(CH3)CH2OCH2CH3

E) CH3CH2CH(CH3)CHOCH2CH3

22) The condensed structural formula for the molecule shown in the figure is ________.

A) C8H14

B) CH3CH2C(CH3)3CH2CH3

C) (CH3)2CHCH(CH3)CH(CH3)2

D) CH3CHCH3CH2(CH3)2

E) CH3CH2CH(CH3)2CH

23) The molecular formula for the molecule shown in the figure is ________.

A) C4H4

B) C4H6

C) C4H8

D) C4H10

E) C4H12

24) The condensed structural formula for the molecule shown in the figure is ________.

A) C6H16O2

B) CH3CH2CH(CH3)3CO2H

C) (CH3)2CH(CH2)2CO2H

D) (CH3)2CHCH(CH3)CO2H

E) CH3CH2CH(CH3)2CO2H

25) The condensed structural formula for the molecule shown in the figure is ________.

A) (CH3)2CH(CH2)2CH3

B) (CH3)2CHCH2CH3

C) CH3CH2CH3(CH2)2

D) CH3CH2CH3(CH3)2

E) CH3CHCH3(CH3)2

26) The condensed structural formula for the molecule shown in the figure is ________.

A) (CH3)2CH(CH2)2CH3

B) (CH3)2CHCH2(CH3)2

C) (CH3)3CCH2CH(CH3)2

D) CH3CH2CH3(CH3)2

E) CH3CHCH3(CH3)2

27) Which of the following formulas represents a straight-chain molecule that is saturated?

A) C3H8

B) C5H10

C) CH2CHCH3

D) CH2CHCH2CH3

E) C4H8

28) Which of the following formulas represents a molecule that is unsaturated?

A) C3H8

B) C5H12

C) CH2CHCH3

D) CH3CH3

E) C7H16

29) Which of the following formulas could represent a straight-chain molecule that is an alkyne?

A) C3H8

B) C5H12

C) C3H6

D) C4H8

E) C7H12

30) Which of the following formulas represent an alkene?

A) C3H8

B) C5H12

C) CH2CHCH3

D) CH3CH3

E) C7H16

31) Arrange the alkanes in the figure in order of increasing boiling point.

A) I < II < III

B) I < III < II

C) II < I < III

D) II < III < I

E) III < II < I

32) Arrange the following compounds in order of increasing strength of intermolecular forces:

CH3CH3, CH3CH2CH3, CH4

A) CH3CH3 < CH3CH2CH3 < CH4

B) CH3CH3 < CH4 < CH3CH2CH3

C) CH4 < CH3CH2CH3 < CH3CH3

D) CH4 < CH3CH3 < CH3CH2CH3

E) CH3CH2CH3 < CH3CH3 < CH4

33) Arrange the following compounds in order of increasing strength of intermolecular forces:

CH3CH3, CH3CH2CH2CH3, CH3CH2CH3

A) CH3CH3 < CH3CH2CH2CH3 < CH3CH2CH3

B) CH3CH2CH2CH3 <CH3CH2CH3 <CH3CH3

C) CH3CH2CH3 <CH3CH3 < CH3CH2CH2CH3

D) CH3CH3 < CH3CH2CH3 < CH3CH2CH2CH3

E) CH3CH2CH2CH3 < CH3CH3 < CH3CH2CH3

34) What is the name of the straight-chain alkane CH3CH2CH2CH3?

A) ethane

B) propane

C) pentane

D) hexane

E) butane

35) What is the name of the straight-chain alkane CH3CH2CH2CH2CH3?

A) ethane

B) propane

C) pentane

D) hexane

E) butane

36) What is the name of the straight-chain alkane CH3CH2CH2CH2CH2CH3?

A) heptane

B) propane

C) pentane

D) hexane

E) butane

37) What is the name of the straight-chain alkane CH3CH2CH3?

A) ethane

B) propane

C) pentane

D) methane

E) butane

38) What is the IUPAC name of the compound shown in the figure?

A) pentane

B) butane

C) methylbutane

D) 3-methylbutane

E) methylpentane

39) What is the IUPAC name of the compound shown in the figure?

A) 3-methyl-4-ethyldecane

B) 4-ethyl-3-methyldecane

C) ethyl-methyl-decane

D) methyl-ethyl-decane

E) 3-methyl-4-propyldecane

40) What is the IUPAC name of the compound shown in the figure?

A) 2-ethylpentane

B) ethylpentane

C) heptane

D) 3-methylhexane

E) 4-methylhexane

41) There are ________ possible isomers with the formula C6H14.

A) 1

B) 2

C) 3

D) 4

E) 5

42) There are ________ possible isomers with the formula C5H12.

A) 1

B) 2

C) 3

D) 4

E) 5

43) There are ________ possible isomers with the formula C4H10.

A) 1

B) 2

C) 3

D) 4

E) 5

44) What can be said about the two structural formulas shown in the figure?

A) They represent isomers.

B) They have different molecular formulas.

C) They represent compounds with the same IUPAC name.

D) They represent the same compound.

E) None of the above.

45) What is the name of the compound CH3CH2CH2CH(CH3)CH3?

A) hexane

B) 5-methylpentane

C) 2-methylpentane

D) 2-butylethane

E) heptane

46) What is the name of the compound CH3CH2CH(CH3)CH3?

A) pentane

B) 2-methylbutane

C) 3-methylbutane

D) 1,1-dimethylpropane

E) 3,3-dimethylpropane

47) There are many isomers of octane in gasoline. What is the name of the compound with the formula CH3C(CH3)2CH2CH(CH3)CH3?

A) octane

B) 2,4-dimethylpentane

C) 2,2,4-methylpentane

D) 2,2,4-trimethylpentane

E) 2,4,4-methylpentane

48) What is the name of the compound CH3C(CH3)2CH(CH2CH3)CH2CH3?

A) nonane

B) 2-methyl-3-ethylpentane

C) 2,2-diethyl-3-ethylpentane

D) 2,2-dimethyl-3-ethylpentane

E) 3-ethyl-2,2-dimethylpentane

49) What is the name of the compound CH3CH(CH3)2?

A) 2,2-methylethane

B) 2,2-dimethylethane

C) 1-methylpropane

D) 2-methylpropane

E) 3-methylpropane

50) What is the condensed structural formula for 2-methylpropane?

A) CH3CH(CH3)2

B) CH3CH2(CH3)2

C) CH3C(CH3)3

D) (CH3)2CH3

E) (CH3)2CH

51) What is the condensed structural formula for 3,3-diethyl-2-methylpentane?

A) CH3CH(CH3)2CH(CH2CH3)CH2CH3

B) CH3CH(CH3)C(CH2CH3)2CH2CH3

C) CH3CH2(CH3)CH(CH2CH3)2CH2CH3

D) CH3CH2(CH3)CH2(CH2CH3)CH2CH3

E) CH3C(CH3)2CH(CH2CH3)CH2CH3

52) What is the condensed structural formula for 3-ethyl-4-methylheptane?

A) CH3CH2CH2CH2CH(CH3)CH(CH2CH3)CH2CH3

B) CH3CH2CH2CH2C(CH3)2CH(CH2CH3)CH2CH3

C) CH3CH2CH2CH(CH3)CH(CH2CH3)CH2CH3

D) CH3CH2CH2CH(CH2CH3)CH(CH2CH3)CH2CH3

E) CH3CH2CH2CH(CH2CH3)CH2(CH3)CH2CH3

53) What is the condensed structural formula for 3,3-diethyl-2-methylhexane?

A) CH3CH2CH(CH2CH3)CH2(CH3)CH2CH3

B) CH3CH2C(CH2CH3)2CH2(CH3)CH2CH3

C) CH3CH2C(CH2CH3)2C(CH3)2CH2CH3

D) CH3CH(CH3)C(CH2CH3)2CH2CH2CH3

E) CH3C(CH3)2C(CH2CH3)2CH2CH2CH3

54) Select the line drawing for 2-methylhexane.

A) A

B) B

C) C

D) D

E) E

55) Select the line drawing for 2,3-dimethylpentane.

A) A

B) B

C) C

D) D

E) E

56) Select the line drawing for 3,3-diethylhexane.

A) A

B) B

C) C

D) D

E) E

57) Predict the product(s) of the reaction

CH3CH3 + Br2

A) CH3BrCH3Br

B) CH2BrCH2Br + H2

C) CH3CH2Br + HBr

D) no reaction

E) 2 CH3Br

58) Predict the product(s) of the reaction

CH3CH3 + Cl2

A) CHClCH3Cl

B) CH2ClCH2Cl + H2

C) no reaction

D) CH3CH2Cl + HCl

E) 2 CH3Cl

59) Predict the product(s) of the reaction between CH3CH(CH3)CH2CH3 and O2 in the presence of a spark.

A) CH3CO(CH3)CH2CH3 + OH

B) CH3CO(CH3)OCH2CH3 + H2

C) no reaction

D) CO2 + H2O

E) CH3CH(CH3)O + CH3CH2O

60) What is the IUPAC name of the compound shown in the figure?

A) butyne

B) 1-butene

C) 2-butene

D) 1-pentene

E) butene

61) What is the IUPAC name of the compound shown in the figure?

A) methylhexene

B) 4-methylhexene

C) 2-methylhexene

D) 4-methyl-1-hexene

E) 4-ethyl-5-pentene

62) Which of the following represents a trans isomer of a compound that can exhibit cis-trans isomerism?

A) A

B) B

C) C

D) D

E) E

63) What is the name of the compound shown in the figure?

A) trans-2,3-diethyl-2-butene

B) 2,3-dimethyl-2-hexene

C) cis-2,3-diethyl-2-butene

D) trans-2,3-dimethyl-2-hexene

E) trans-4,5-dimethyl-4-hexene

64) What is the name of the compound shown in the figure?

A) trans-2,3-diethyl-2-butene

B) trans-3,4-dimethyl-3-hexene

C) cis-2,3-diethyl-2-butene

D) cis-3,4-dimethyl-3-hexene

E) 3-octene

65) What is the name of the compound CH3CH=CHC(CH3)3?

A) 2,2-dimethyl-4-pentene

B) trimethylbutene

C) 2-heptene

D) 4,4-dimethyl-2-pentene

E) 1,1,1-trimethyl-2-butene

66) Which of the following represents a cis isomer of a compound that can exhibit cis-trans isomerism?

A) A

B) B

C) C

D) D

E) E

67) What is the name of the compound shown in the figure?

A) trans-2,3-diethyl-2-butene

B) trans-3,4-dimethyl-3-hexene

C) cis-2,3-diethyl-2-butene

D) cis-3,4-dimethyl-3-hexene

E) 3-octene

68) Which of the following compounds can exist as cis/trans isomers?

A) CH3CH=CHC(CH3)3

B) CH3CH=CH2

C) CH2=CH2

D) CH3CH(CH3)2

E) CH2=CHCH2CH3

69) Which of the following compounds can exist as cis/trans isomers?

A) CH3CH2CH=CH2

B) CH3CH=CH2

C) CH2=CH2

D) CH3CH=CHCH3

E) CH2=CHCH2CH2CH3

70) Predict the product(s) of the reaction of ethene and bromine:

CH2=CH2 + Br2 → ?

A) no reaction

B) CH3CH2Br + HBr

C) CH2BrCH2Br + H2

D) CH2BrCH2Br

E) CH2=CHBr + HBr

71) Predict the product(s) of the reaction of ethene and hydrogen, catalyzed by palladium metal:

CH2=CH2 + H2 ?

A) no reaction

B) CH2=CH3

C) CH3=CH3

D) CH3CH3

E) 2 CH4

72) Predict the product(s) of the reaction between ethene and hydrogen bromide:

CH2=CH2 + HBr → ?

A) no reaction

B) CH2=CH2Br

C) CH3=CH2Br

D) CH3CH2Br

E) CH4 + CH3Br

73) Which types of compounds undergo addition polymerization reactions?

A) alkanes

B) alkenes

C) alcohols

D) aromatic compounds

E) amines

74) Give the IUPAC name for the compound shown in the figure.

A) 2,3-bromobenzene

B) 2,3-dibromobenzene

C) 1,2-bromobenzene

D) 1,2-dibromobenzene

E) benzenedibromide

75) Give the IUPAC name for the compound shown in the figure.

A) 2-aminobenzene

B) 2-aminocyclohexene

C) aniline

D) ammonia benzene

E) benzene ammonia

76) Give the IUPAC name for the compound shown in the figure.

A) 1-chloro-3-ethylbenzene

B) 1-chloro-4-ethylbenzene

C) 1-ethyl-2-chlorobenzene

D) 1-ethyl-4-chlorobenzene

E) chloroethylcyclohexane

77) Give the IUPAC name for the compound shown in the figure.

A) 4-ethyl-1-methylbenzene

B) 3-ethyltoluene

C) 4-ethyltoluene

D) 1-methyl-phenylethane

E) 4-ethyl-1-methylcyclohexane

78) Identify the major product of the following catalyzed reaction.

A) A

B) B

C) C

D) D

E) No products.

79) Which of the following formulas represents an alcohol?

A) CH3COCH3

B) CH3OCH3

C) CH3OCH2CH3

D) CH3CH2CH2OH

E) CH3CH2CH2CHO

80) Which of the following formulas represents an alcohol?

A) CH3CH2CHO

B) CH3CH2OCH2CH3

C) CH3CH(OH)CH2CH3

D) CH3COCH2CH3

E) CH3CO2H

81) Which of the following formulas represents an alcohol?

A) CH3CH2CHO

B) CH3OCH3

C) (CH3)2C(OH)CH3

D) CH3CO2H

E) CH3OCH2CH3

82) What is the IUPAC name for the compound shown in the figure?

A) 3-methylalcohol

B) 3-methyl-3-hexanol

C) 3-methylhexanol

D) 5-methylhexanal

E) 5-methylhaxane-5 hydroxide

83) What is the IUPAC name for the compound shown in the figure?

A) 3-methylbutanol

B) 4-methylpentanol

C) 2-methyl-1-butanol

D) 3-methyl-1-pentanol

E) hexanol

84) Name the compound (CH3)2C(OH)CH2CH2CH3 using the IUPAC system.

A) 1,1-dimethyl-2-butanol

B) 1,1-dimethyl-1-butanol

C) 2-methyl-4-pentanol

D) 2-methyl-2-pentanol

E) 3-methyl-4-pentanol

85) Name the compound (CH3)2CHCH2CH2CH2OH using the IUPAC system.

A) 2-methyl-5-pentanol

B) 4-methyl-1-pentanol

C) 1,1-dimethyl-4-butanol

D) 4,4-dimethyl-1-butanol

86) Which of the following formulas represents an ether?

A) CH3CH2CHO

B) CH3OCH3

C) (CH3)2C(OH)CH3

D) CH3CO2H

E) CH3COCH2CH3

87) Which of the following formulas represents an ether?

A) CH3CH2CHO

B) CH3COCH2CH3

C) CH3CH(OH)CH2CH3

D) CH3CH2OCH2CH3

E) CH3CO2H

88) Rank the following compounds in order of increasing boiling point: CH3OCH3, CH3CH2OH, CH3CH2CH3

A) CH3OCH3 < CH3CH2OH < CH3CH2CH3

B) CH3OCH3 < CH3CH2CH3 < CH3CH2OH

C) CH3CH2CH3 < CH3CH2OH < CH3OCH3

D) CH3CH2CH3 < CH3OCH3 < CH3CH2OH

E) CH3CH2OH < CH3OCH3 < CH3CH2CH3

89) Rank the following compounds in order of increasing boiling point: CH3OCH2CH3, CH3CH2CH2OH, CH3CH2CH2CH3

A) CH3OCH2CH3 < CH3CH2CH2OH < CH3CH2CH2CH3

B) CH3OCH2CH3 < CH3CH2CH2CH3 < CH3CH2CH2OH

C) CH3CH2CH2OH < CH3OCH2CH3 < CH3CH2CH2CH3

D) CH3CH2CH2CH3 < CH3OCH2CH3 < CH3CH2CH2OH

E) CH3CH2CH2CH3 < CH3CH2CH2OH < CH3OCH2CH3

90) Give the common name for the compound CH3CH2CH2-O-CH2CH3.

A) ethane propane ether

B) ethyl propyl ether

C) propyl ethyl ether

D) diethyl ether

E) dipropyl ether

91) Give the common name for the compound CH3CH2CH2-O-CH3.

A) methane propane ether

B) methyl propyl ether

C) propyl methyl ether

D) methyl propyl ketone

E) propyl methyl ketone

92) Give the common name for the compound CH3CH2-O-CH3.

A) methane ethane ether

B) methyl propyl ether

C) ethyl methyl ether

D) methyl ethyl ketone

E) ethyl methyl ketone

93) Give the common name for the compound shown in the figure.

A) methane ethane ether

B) methyl propyl ether

C) ethyl methyl ether

D) methyl ethyl ketone

E) ethyl methyl ketone

94) Select the correct condensed structural formula for ethyl methyl ether.

A) CH3CH(OH)CH3

B) CH3CH2COCH3

C) CH3COCH3

D) CH3OCH2CH3

E) CH3OCH3

95) Which of the following formulas represents an aldehyde?

A) CH3CH2OH

B) CH3CH2COCH3

C) CH3OCH3

D) CH3COCH3

E) CH3CHO

96) Which of the following formulas represents an aldehyde?

A) CH3OH

B) CH3COCH3

C) CH3CH2CHO

D) CH3CH2COCH3

E) CH3CO2H

97) Which of the following formulas represents a ketone?

A) CH3OH

B) CH3COCH3

C) CH3CH2CHO

D) CH3CH2OCH2CH3

E) CH3CO2H

98) Which of the following formulas represents a ketone?

A)  CH3CH2OH

B) CH3CH2CO2H

C) CH3OCH3

D) CH3CH2COCH3

E) CH3CHO

99) Rank the following in order of increasing boiling point:

CH3CH2NH2, CH3CH3, CH3NH2

A) CH3CH2NH2 < CH3CH3 < CH3NH2

B) CH3CH2NH2 < CH3NH2 < CH3CH3

C) CH3NH2 < CH3CH3 < CH3CH2NH2

D) CH3NH2 < CH3CH2NH2 < CH3CH3

E) CH3CH3 < CH3NH2 < CH3CH2NH2

100) Rank the following in order of increasing boiling point:

C2H6, C4H10, C6H14

A) C2H6 < C4H10 < C6H14

B) C2H6 < C6H14< C4H10

C) C6H14 < C4H10 < C2H6

D) C6H14 < C2H6 < C4H10

E) They should have the same boiling

101) Which of the following is the molecular formula for the aniline shown in the figure?

A) C6H11NH2

B) C6H5NH2

C) C7H7NH2

D) C7NH2

E) C6NH2

102) An unsaturated hydrocarbon is one that will absorb water.

103) The compound 2-butyne can exist as cis-trans isomers.

104) Both alkenes and alkynes can undergo addition reactions.

105) The compound shown in the figure is aromatic.

106) Aromatic compounds readily undergo addition reactions.

107) Linoleic acid is a long-chain unsaturated carboxylic acid with a bent chain. It has a higher melting point than stearic acid, a straight-chain saturated carboxylic acid with the same chain length.

108) Esters can be formed by a condensation reaction between a carboxylic acid and an alcohol.

109) An amine is an organic base.

110) A branched-chain alkane will have a higher boiling point than a straight-chain alkane with the same number of carbons.

111) The number of possible isomers of an organic compound increases rapidly as the number of carbon atoms increases.

112) The line structure shown represents a molecule of cyclobutane.

113) The following ball-and-stick model represents a molecule of butane.

114) The following line structure represents a molecule of octane.

115) The following line structure represents a molecule of 5-methyl-1-pentene.

116) The following line structure represents a molecule of propyne.

117) The following is a correct equation that describes the reaction of benzene (C6H6) with chlorine (Cl2) in the presence of an FeCl3 catalyst:

C6H6 + Cl2  C6H5Cl + HCl 

118) The reagents CH3CH2CO2H and CH3OH can combine in a condensation reaction to produce the ester CH3CH2CO2CH3.

119) The boiling point of CH3CH2CO2H is greater than CH3CH2CHO because CH3CH2CO2H has particularly strong hydrogen bonding interactions between molecules while CH3CH2CHO does not.

120) Both of the line structures shown represent a molecule of dimethylamine:

(CH3)2NH.

121) The line structure shown represents the molecule with the formula

CH3NH2.

122) Classify the following compound based on its functional group:

(CH3)2NH.

123) Classify the following compound based on its functional group:

CH3CH2CH2OH.

124) Classify the following compound based on its functional group:

CH3CH2CO2H.

125) Classify the molecule shown in the figure based on its functional group.

126) Classify the molecule shown in the figure based on its functional group.

127) Classify the molecule shown in the figure based on its functional group.

128) Which should be more soluble in water, dimethyl ether, CH3OCH3, or ethanol, CH3CH2OH? Explain your answer.

129) The solubility of CH3CH2CHO is 20 mL/100 mL of water, while CH3CHO is soluble in water in any proportions. Explain why the two compounds differ in solubility.