alkanes (ch.3)

QOI 0809

-

ALKANES

Name___________________________________

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

1) Which of the statements below accurately describe(s) alkanes?

A) Alkanes are hydrocarbons which contain only single bonds.

B) Alkanes belong to the class of unsaturated hydrocarbons.

C) Alkanes are the simplest and least reactive class of organic compounds.

D) both A and B

E) both A and C

1)

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

2) If a hydrocarbon has no double or triple bonds, it is said to be __________.

2)


3) If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain?

A) n B) 2n C) n

+

2 D) 2n

+

2 E) n

-

2

3)


4) Straight

chain alkanes are also called __________.

4)

ESSAY. Write your answer in the space provided or on a separate sheet of paper.

5) Predict the molecular formula of 4

ethyl

-

5,5

dimethyldodecane.

6) Give structures for the three isomers with molecular formula C5H12 and provide the common name of each.

7) Provide an acceptable name for the alkane shown below.

CH3CH2CH2CH2CH2CH3



1




13) Draw an acceptable structure for 4

tert

butyloctane.


ethyl

-

6

-

(1,2

dimethylpropyl)decane.


ethyl

-

2

-

(2,2

dimethylpentyl)cyclopentane.


ethyl

-

3

methylhexane.


isopropyl

-

2

methylheptane.


ethyl

-

2,6,7

trimethyl

-

5

propylnonane.



2

21) List three commercial products which are composed primarily of alkanes.

22) Why are alkanes described as hydrophobic?


23) When one compares the densities of n

hexane and water, one finds:

A) that n

hexane is less dense than water.

B) that n

hexane is more dense than water.

C) that these two compounds have the same density.

D) that the relative densities of two immiscible compounds cannot be measured.

23)


24) Which intermolecular force is primarily responsible for the interactions among alkane molecules?


25) Consider the three isomeric alkanes n

hexane, 2,3

dimethylbutane, and 2

methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point?

A) 2,3

dimethylbutane

<

2

methylpentane

< n

hexane

B) 2

methylpentane

< n

hexane

<

2,3

dimethylbutane

C) 2

methylpentane

<

2,3

dimethylbutane

< n

hexane

D) n

hexane

<

2

methylpentane

<

2,3

dimethylbutane

E) n

hexane

<

2,3

dimethylbutane

<

2

methylpentane

25)


26) A branched alkane generally melts at a __________ temperature than the containing the same number of carbons.

n

alkane 26)

27) __________ is the n

alkane of greatest molecular weight which is a gas at room temperature and pressure.


28) Which alkanes have largely replaced Freons as propellants in aerosol cans?

A) methane and ethane

B) propane and butane

C) pentane and hexane

D) nonane and decane

E) none of the above

28)

29) How many carbons do the primary alkane constituents of gasoline contain?

A) C1



C2 B) C3



C4 C) C5



C8 D) C8



C12 E) C12



27)

C16

29)


30) Name the two major steps in the refining of crude oil into usable hydrocarbon products.

3


31) What is the major constituent of natural gas?

A) octane B) butane C) propane D) ethane E) methane

31)


32) By using the appropriate molecular formulas, write a balanced equation which describes the complete combustion of nonane.


33) __________ is the reaction process through which long mixture of short

chain alkanes and alkenes.

chain alkanes are converted into a 33)


34) Draw a Newman projection of the most stable conformation of 2

methylpropane.


35) The structures below are: 35)

A) not isomers.

B) conformational isomers.

C) cis

trans isomers.

D) structural isomers.

E) both B and D


36) Define the term conformation.

37) Use a sawhorse structure to depict the eclipsed conformer of ethane.

38) View a butane molecule along the C2



C3 bond and provide a Newman projection of the lowest energy conformer.

39) Provide a representation of the gauche conformer of butane.

4


40) Among the butane conformers, which occur at energy minima on a graph of potential energy versus dihedral angle?

A) gauche only

B) eclipsed and totally eclipsed

C) gauche and anti

D) eclipsed only

E) anti only

40)


41) Give the IUPAC name for the cycloalkane shown below.

42) Give the IUPAC name for the cycloalkane shown below.


43) Which of the following cycloalkanes exhibits the greatest molar heat of combustion?

A) cyclooctane

B) cycloheptane

C) cyclohexane

D) cyclobutane

E) cyclopropane

43)

44) 44) Which of the following correctly ranks the cycloalkanes in order of increasing ring strain per methylene?

A) cyclopropane

<

cyclobutane

<

cyclohexane

<

cyclopentane

B) cyclohexane

<

cyclopentane

<

cyclobutane

<

cyclopropane

C) cyclohexane

<

cyclobutane

<

cyclopentane

<

cyclopropane

D) cyclopentane

<

cyclopropane

<

cyclobutane

<

cyclohexane

E) cyclopropane

<

cyclopentane

<

cyclobutane

<

cyclohexane


45) Describe the sources of angle strain and torsional strain present in cyclopropane.

5


46) Which of the following statements is a correct description of the most stable conformation of

1,1,3

trimethylcyclohexane?

A) The methyl group at C

-

3 is equatorial.

B) C

-

1 is a tertiary carbon and C

-

3 is a primary carbon.

C) C

-

1 is a quaternary carbon and C

-

3 is a secondary carbon.

D) C

-

1 is a tertiary carbon and C

-

3 is a secondary carbon.

E) Both methyl groups at C

-

1 are equatorial.

46)


47) Draw the most stable conformation of trans

-

1,2

dimethylcyclohexane.

48) Draw the most stable conformation of cis

-

1,2

dimethylcyclohexane.


49) Which of the statements below correctly describes the chair conformations of trans

-

1,4

dimethylcyclohexane?

A) The two chair conformations are of equal energy.

B) The higher energy chair conformation contains one axial methyl group and one equatorial methyl group.

C) The lower energy chair conformation contains one axial methyl group and one equatorial methyl group.

D) The higher energy chair conformation contains two axial methyl groups.

E) The lower energy chair conformation contains two axial methyl groups.

49)

50) Which of the statements below correctly describes the chair conformations of trans

-

1,3

diethylcyclohexane.

A) The two chair conformations are equal in energy.

B) The higher energy chair conformation contains two axial ethyl groups.

C) The higher energy chair conformation contains two equatorial ethyl groups.

D) The lower energy chair conformation contains two axial ethyl groups.

E) The lower energy chair conformation contains two equatorial ethyl groups.

50)


51) Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and the equatorial hydrogens (He).


-

1

tert

butyl

-

3

ethylcyclohexane.


53) Which of the following correctly lists the conformations of cyclohexane in order of increasing energy?

A) chair

<

boat

<

twist

<

half

chair

B) half

chair

<

boat

<

twist

<

chair

C) chair

<

twist

<

half

chair

<

boat

D) chair

<

twist

<

boat

<

half

chair

E) half

chair

<

twist

<

boat

<

chair

53)

6

54) In the boat conformation of cyclohexane, the "flagpole" hydrogens are located:

A) on the same carbon.

B) on adjacent carbons.

C) on C

-

1 and C

-

3.

D) on C

-

1 and C

-

4.


55) The energy difference between the axial and equatorial conformers of methylcyclohexane is:

A)

<

0.1 kcal/mol

B) 0.9 kcal/mol

C) 1.7 kcal/mol

D) 2.5 kcal/mol

E)

>

5.0 kcal/mol



-

1

ethyl

-

3

methylcyclohexane.


-

1

ethyl

-

4

isopropylcyclohexane.

58) Provide an acceptable structure for spiro [4.4]nonane.

54)

55)


59) Which of the following is a bridged bicyclic alkane?

A) cis

decalin

B) bicyclo[2.2.1]heptane

C) bicyclo[3.2.0]heptane

D) bicyclo[4.1.0]heptane


59)


60) Provide an acceptable name for the compound below.


61) If a cyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also contain?

A) n B) 2n C) n

+

2 D) 2n

+

2 E) n

-

2

61)

7




63) A series of compounds, like the n

alkanes, that differ only by the number of groups, is called a(n) __________ series.

 CH2 

63)


64) Within the context of commercial uses of alkanes, explain what "knocking" is.

65) By using the appropriate molecular formulas, write a balanced equation which describes the complete combustion of cyclohexane.

66) From the perspective of viewing down the C2



C3 bond, draw the Newman projection of the most stable conformation of 2,3

dimethylbutane.

67) From the perspective of viewing down the C2

-

C3 bond, draw the Newman projection of the least stable conformation of 2,3

dimethylbutane.


68) Which of the following best describes the molecules of a sample of ethane gas at room temperature?

A) Almost all of the molecules are frozen or locked in the eclipsed conformation.

B) Almost all of the molecules are frozen or locked in the staggered conformation.

C) The molecules are rapidly interconverting between the eclipsed and staggered conformations, but at any one time slightly more of them are present in the eclipsed conformation.

D) The molecules are rapidly interconverting between the eclipsed and staggered conformations, but at any one time slightly more of them are present in the staggered conformation.

68)

69) In the lowest energy chair conformation of cis

-

1,3

dimethylcyclohexane, how many axial positions are occupied by hydrogen atoms?

A) 2 B) 3 C) 4 D) 5 E) 6

69)



decalin.

8


71) Which of the following types of hydrocarbons is(are) saturated?

A) alkanes

B) alkenes

C) alkynes

D) aromatics

E) All of the above are saturated.

71)


72) Provide an acceptable name for the following compound.

72)

73) Provide an acceptable name for the following compound.

73)

74) Provide an acceptable name for the [(CH3)3C]2CHCH3.

74)


75) Which of the following statements concerning the conformers of butane is true?

A) Unlike ethane, all butane conformers are classified as eclipsed.

B) The lowest energy conformer of butane is the gauche conformer.

C) There is more torsional strain in the anti conformer than in the totally eclipsed conformer.

D) The eclipsed and totally eclipsed conformers have the same amount of nonbonded strain.

E) The gauche and anti conformers differ primarily in the amount of nonbonded strain present.

75)


76) Arrange the following conformers of butane in order of energy, lowest to highest: eclipsed, totally eclipsed, gauche, and anti.

76)

9


77) Which of the following statements regarding cyclobutane is correct?

A) The lowest energy conformation of cyclobutane is a planar one in which all of the bond angles is 90°.

B) The lowest energy conformation of cyclobutane is known as the chair conformation.

C) The lowest energy conformation is one in which the bond angles are slightly less than 90° even though this increases angle strain.

D) The lowest energy conformation is one in which the bond angles are greater than 90° so that angle strain is significantly reduced.

E) None of the above statements is correct.

77)

78) In the lowest energy conformation of the compound below, how many alkyl substituents are equatorial?

78)

A) 0 B) 1 C) 2 D) 3 E) 6

79) In the lowest energy conformation of the compound below, how many alkyl substituents are axial?

79)

A) 0 B) 1 C) 2 D) 3 E) 6


80) Provide an acceptable name for (CH3CH2CH2)3CH.

80)


-

1

t

butyl

-

4

methylcyclohexane.

81)

82) Draw the Newman projection of the highest energy conformation that results from rotation about the C2

-

C3 bond of 2,2

dimethylbutane.

82)

83) Draw the Newman projection of the lowest energy conformation that results from rotation about the C2

-

C3 bond of 2

methylbutane.

83)

84) Draw the Newman projection of the lowest energy conformation that results from rotation about the C2

-

C3 bond of 2,2

dimethylbutane.

84)

85) Draw the Newman projection of the highest energy conformation that results from rotation about the C2

-

C3 bond of 2

methylbutane.

85)

10

86) In the complete combustion of heptane, how many moles of water are produced?

86)

87) Provide the IUPAC name of (CH3CH2)3CH.

88) Provide the IUPAC name of (CH3)2CHCH2CH2C(CH3)3.

87)

88)


89) Which of the following cycloalkanes has the smallest heat of combustion per CH2 group?

A) cyclopropane

B) cyclobutane

C) cyclopentane

D) cyclohexane

E) cycloheptane

89)

90) Which has the greatest molar heat of combustion?

A) trans

-

1,2

dimethylcyclopentane

B) cis

-

1,2


C) trans

-

1,3


D) methylcyclohexane

E) cycloheptane

90)

91) Identify the correct IUPAC name for the following structure.

91)

A) 6

bromo

-

1

cyclopentyl

-

3,6

dimethylhexane

B) 1

bromo

-

5

cyclopentyl

-

1,4

dimethylpentane

C) 2

bromo

-

6

cyclopentyl

-

5

methylhexane

D) 5

bromo

-

1

cyclopentyl

-

2

methylhexane


92) Identify the correct IUPAC name for each compound shown below.

92)

A) 2

bromo

-

3

sec

butyl

-

4

ethylhexane

B) 2

bromo

-

4

ethyl

-

3

sec

butylhexane

C) 3

-

(1

bromoethyl)

-

2,4

diethylhexane

D) 4

-

(1

bromoethyl)

-

3

ethyl

-

5

methylheptane

E) 4

-

(1

bromoethyl)

-

5

ethyl

-

3

methylheptane

11

93) Identify the correct IUPAC name for the structure shown below.

93)

A) 1

tert

butyl

-

2

chloro

-

5

bromocycloheptane

B) 5

bromo

-

1

tert

butyl

-

2

chlorocycloheptane

C) 1

bromo

-

4

chloro

-

5

tertbutylcycloheptane

D) 1

bromo

-

4

tert

butyl

-

5

chlorocycloheptane

E) 1

tert

butyl

-

4

bromo

-

7

chlorocycloheptane

94) Which of the following describes the compound below?

94)

A) bridged bicyclic

C) spiro bicyclic

B) fused bicyclic

D) bridged tricyclic

95) The energy barrier for carbon

carbon bond rotation in propane is mainly due to __________.

A) angle strain

B) bond strain

C) muscle strain

D) steric strain

E) torsion strain


Use the following Newman projection for the question(s) below.

95)

96) Without any change in conformation, translate the Newman projection shown above to a perspective structure.

96)


97) For the compound represented by the Newman projection above, what is the dihedral angle between the methyl groups in the conformer that has the smallest molecular dipole moment?

A) 0 ∘ B) 30 ∘ C) 60 ∘ D) 120 ∘ E) 180 ∘

97)

98) Which of the following difluorocyclohexane isomers has the greatest molecular dipole in its least stable chair conformation?

A) cis 1,2

difluorocyclohexane

C) cis 1,3

difluorocyclohexane

B)

D) trans trans

1,2

1,3

-

difluorocyclohexane difluorocyclohexane

98)

12

Answer Key

Testname: UNTITLED7

1) E

ID: oc6w 3

-

1

Diff: 1

Skill:

2) saturated

ID: oc6w 3

-

2

Diff: 1

Skill:

3) D

ID: oc6w 3

-

3

Diff: 2

Skill:

4) n

alkanes

ID: oc6w 3

-

4

Diff: 2

Skill:

5) C16H34

ID: oc6w 3

-

5

Diff: 2

Skill:

6)

ID: oc6w 3

-

6

Diff: 3

Skill:

7) hexane or n

hexane

ID: oc6w 3

-

7

Diff: 1

Skill:

8) 2,5

dimethylheptane

ID: oc6w 3

-

8

Diff: 1

Skill:

9) 5

sec

butyl

-

2,2

dimethylnonane or 2,2

dimethyl

-

5

-

(1

methylpropyl)nonane

ID: oc6w 3

-

9

Diff: 2

Skill:

10) 4

isopropyldecane or 4

-

(1

methylethyl)decane

ID: oc6w 3

-

10

Diff: 2

Skill:

11) 3

ethyl

-

7

methyl

-

5

propylnonane

ID: oc6w 3

-

11

Diff: 3

Skill:

13

Answer Key

Testname: UNTITLED7

12) 3

ethyl

-

4,4

dimethylheptane

ID: oc6w 3

-

12

Diff: 2

Skill:

13)

14)

ID: oc6w 3

-

13

Diff: 1

Skill:

15)

ID: oc6w 3

-

14

Diff: 3

Skill:

16)

ID: oc6w 3

-

15

Diff: 3

Skill:

17)

ID: oc6w 3

-

16

Diff: 1

Skill:

ID: oc6w 3

-

17

Diff: 1

Skill:

14

Answer Key

Testname: UNTITLED7

18)

ID: oc6w 3

-

18

Diff: 2

Skill:

19) 2,2,3,6

tetramethylheptane

ID: oc6w 3

-

19

Diff: 2

Skill:

20) 6

ethyl

-

2

methyl

-

5

propyldecane

ID: oc6w 3

-

20

Diff: 2

Skill:

21) natural gas, gasoline, kerosene, heating oil, lubricating oil, liquefied petroleum gas, jet fuel, diesel oil, petroleum jelly

ID: oc6w 3

-

21

Diff: 2

Skill:

22) Alkanes are nonpolar and as such they do not dissolve to any appreciable extent in water.

ID: oc6w 3

-

22

Diff: 2

Skill:

23) A

ID: oc6w 3

-

23

Diff: 1

Skill:

24) van der Waals or London forces

ID: oc6w 3

-

24

Diff: 2

Skill:

25) A

ID: oc6w 3

-

25

Diff: 2

Skill:

26) higher

ID: oc6w 3

-

26

Diff: 2

Skill:

27) Butane

ID: oc6w 3

-

27

Diff: 2

Skill:

28) B

ID: oc6w 3

-

28

Diff: 2

Skill:

15

Answer Key

Testname: UNTITLED7

29) C

ID: oc6w 3

-

29

Diff: 2

Skill:

30) 1. fractional distillation

2. cracking (catalytic cracking and/or hydrocracking)

ID: oc6w 3

-

30

Diff: 2

Skill:

31) E

ID: oc6w 3

-

31

Diff: 1

Skill:

32) CH3(CH2)7CH3

+

14 O2

→

9 CO2

+

10 H2O

ID: oc6w 3

-

32

Diff: 3

Skill:

33) Catalytic cracking

ID: oc6w 3

-

33

Diff: 2

Skill:

34)

ID: oc6w 3

-

34

Diff: 2

Skill:

35) D

ID: oc6w 3

-

35

Diff: 2

Skill:

36) Conformations are different arrangements of the same molecule formed by rotations about single bonds.

ID: oc6w 3

-

36

Diff: 2

Skill:

37)

ID: oc6w 3

-

37

Diff: 2

Skill:

16

Answer Key

Testname: UNTITLED7

38)

39)

ID: oc6w 3

-

38

Diff: 3

Skill:

ID: oc6w 3

-

39

Diff: 3

Skill:

40) C

ID: oc6w 3

-

40

Diff: 3

Skill:

41) trans

-

1

ethyl

-

2

methylcyclopentane

ID: oc6w 3

-

41

Diff: 1

Skill:

42) cis

-

1

isopropyl

-

3

methylcycloheptane

ID: oc6w 3

-

42

Diff: 1

Skill:

43) A

ID: oc6w 3

-

43

Diff: 2

Skill:

44) B

ID: oc6w 3

-

44

Diff: 2

Skill:

45) The angle strain arises from the compression of the ideal tetrahedral bond angle of 109.5° to 60°. The large torsional strain occurs since all C



H bonds on adjacent carbons are eclipsed.

ID: oc6w 3

-

45

Diff: 3

Skill:

46) A

ID: oc6w 3

-

46

Diff: 2

Skill:

17

Answer Key

Testname: UNTITLED7

47)

48)

ID: oc6w 3

-

47

Diff: 2

Skill:

ID: oc6w 3

-

48

Diff: 2

Skill:

49) D

ID: oc6w 3

-

49

Diff: 2

Skill:

50) A

ID: oc6w 3

-

50

Diff: 2

Skill:

51)

52)

ID: oc6w 3

-

51

Diff: 1

Skill:

ID: oc6w 3

-

52

Diff: 2

Skill:

53) D

ID: oc6w 3

-

53

Diff: 3

Skill:

54) D

ID: oc6w 3

-

54

Diff: 2

Skill:

18

Answer Key

Testname: UNTITLED7

55) C

ID: oc6w 3

-

55

Diff: 3

Skill:

56)

57)

ID: oc6w 3

-

56

Diff: 2

Skill:

58)

ID: oc6w 3

-

57

Diff: 2

Skill:

ID: oc6w 3

-

58

Diff: 3

Skill:

59) B

ID: oc6w 3

-

59

Diff: 2

Skill:

60) Bicyclo[2.1.1]hexane

ID: oc6w 3

-

60

Diff: 2

Skill:

61) B

ID: oc6w 3

-

61

Diff: 1

Skill:

62) 5

ethyl

-

2,2

dimethylheptane

ID: oc6w 3

-

62

Diff: 2

Skill:

63) homologous

ID: oc6w 3

-

63

Diff: 2

Skill:

64) "Knocking" is the potentially damaging, premature explosive combustion of certain gasoline mixtures in a car's engine.

ID: oc6w 3

-

64

Diff: 1

Skill:

19

Answer Key

Testname: UNTITLED7

65) C6H12

+

9 O2

→

6 CO2

+

6 H2O

ID: oc6w 3

-

65

Diff: 2

Skill:

66)

67)

ID: oc6w 3

-

66

Diff: 3

Skill:

ID: oc6w 3

-

67

Diff: 3

Skill:

68) D

ID: oc6w 3

-

68

Diff: 2

Skill:

69) E

ID: oc6w 3

-

69

Diff: 1

Skill:

70)

ID: oc6w 3

-

70

Diff: 3

Skill:

71) A

ID: oc6w 3

-

71

Diff: 1

Skill:

20

Answer Key

Testname: UNTITLED7

72) 4,4

dichloro

-

6

isopropyl

-

3

methylnonane

ID: oc6w 3

-

72

Diff: 2

Skill:

73) isobutylcyclopentane or 2

methylpropylcyclopentane

ID: oc6w 3

-

73

Diff: 2

Skill:

74) 2,2,3,4,4

pentamethylpentane

ID: oc6w 3

-

74

Diff: 2

Skill:

75) E

ID: oc6w 3

-

75

Diff: 2

Skill:

76) anti

<

gauche

<

eclipsed

<

totally eclipsed

ID: oc6w 3

-

76

Diff: 2

Skill:

77) C

ID: oc6w 3

-

77

Diff: 3

Skill:

78) B

ID: oc6w 3

-

78

Diff: 2

Skill:

79) A

ID: oc6w 3

-

79

Diff: 2

Skill:

80) 4

propylheptane

ID: oc6w 3

-

80

Diff: 1

Skill:

81)

ID: oc6w 3

-

81

Diff: 2

Skill:

21

Answer Key

Testname: UNTITLED7

82)

83)

ID: oc6w 3

-

82

Diff: 1

Skill:

84)

ID: oc6w 3

-

83

Diff: 2

Skill:

85)

ID: oc6w 3

-

84

Diff: 2

Skill:

ID: oc6w 3

-

85

Diff: 2

Skill:

86) 8

ID: oc6w 3

-

86

Diff: 2

Skill:

87) 3

ethylpentane

ID: oc6w 3

-

87

Diff: 2

Skill:

22

Answer Key

Testname: UNTITLED7

88) 2,2,5

trimethylhexane

ID: oc6w 3

-

88

Diff: 2

Skill:

89) D

ID: oc6w 3

-

89

Diff: 2

Skill:

90) B

ID: oc6w 3

-

90

Diff: 3

Skill:

91) D

ID: oc6w 3

-

91

Diff: 3

Skill:

92) D

ID: oc6w 3

-

92

Diff: 3

Skill:

93) B

ID: oc6w 3

-

93

Diff: 3

Skill:

94) A

ID: oc6w 3

-

94

Diff: 2

Skill:

95) E

ID: oc6w 3

-

95

Diff: 1

Skill:

96)

ID: oc6w 3

-

96

Diff: 3

Skill:

97) C

ID: oc6w 3

-

97

Diff: 3

Skill:

98) C

ID: oc6w 3

-

98

Diff: 3

Skill:

23

15)

16)

7)

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17)

1)

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3)

4)

5)

6)

QOI 0809

-

ALKANES

Name___________________________________

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5

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