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chapt 3 exam

Total questions: 135

Worksheet time: 2hrs 32mins

Name
Class
Date
1.

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

a)

A) Alkanes are hydrocarbons which contain only single bonds.

b)

B) Alkanes belong to the class of unsaturated hydrocarbons.

c)

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

d)

D) both A and B

e)

E) both A and C

2.

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.

3.

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

4.

Straight-chain alkanes are also called (a)   .

5.

The structure below is a potent analgesic agent (pain reliever) (J. Med. Chem., 2009, 5685).

How many secondary carbons are in this structure?

a)

2

b)

4

c)

6

d)

12

6.

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

7.

A series of compounds, like the n-alkanes, that differ only by the number of -CH2- groups, is

called a(n) (a)   series.

8.

A bicyclic alkane contains 12 carbon atoms. How many hydrogen atoms does it contain?

a)

20

b)

22

c)

24

d)

26

e)

28

9.

How many methylene groups are present in 2,4-dimethylhexane?

a)

0

b)

1

c)

2

d)

6

e)

8

10.

Triacontane is an unbranched alkane that contains 30 carbon atoms in each molecule. How

many hydrogen atoms are present in each molecule of triacontane?

a)

30

b)

32

c)

58

d)

60

e)

62

11.

How many secondary (2°) carbons are found in 5-ethyl-3,3,4-trimethylheptane?

a)

1

b)

4

c)

3

d)

2

e)

6

12.

Provide an acceptable name for (CH3CH2CH2)3CH

(a)  

13.

Provide the name of the compound below.

(a)  

14.

Provide the name of the compound below.

(a)  

15.

Provide an acceptable name for the alkane shown below.

CH3CH2CH2CH2CH2CH3

(a)  

16.

Provide an acceptable name for the alkane shown below.

(a)  

17.

Draw an acceptable structure for 4-tert-butyloctane

a)

b)

c)

d)

e)

18.

Draw an acceptable structure for 3-ethyl-3-methylhexane

a)

b)

c)

d)

e)

19.

A student named the following molecule "4-isobutylheptane." Why is this incorrect? What is the correct name?

(a)  

20.

Name the haloalkane shown

(a)  

21.

Provide an acceptable name for the following compound

(a)  

22.

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

(a)  

23.

Provide the IUPAC name of (CH3CH2)3CH

(a)  

24.

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

(a)  

25.

Predict the molecular formula of 4-ethyl-5,5-dimethyldodecane

(a)  

26.

Provide an acceptable name for the alkane shown below

(a)  

27.

Provide an acceptable name for the alkane shown below

(a)  

28.

Provide an acceptable name for the alkane shown below

(a)  

29.

Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane.

a)

b)

c)

d)

e)

30.

Provide an acceptable name for the alkane shown below.

(a)  

31.

Provide an acceptable name for the alkane shown below.

(a)  

32.

Provide an acceptable name for the alkane shown below

(a)  

33.

Identify the correct IUPAC name for the following structures.

a)

4-(2-iodo-1-methylethyl)-3-methylheptane

b)

3-s-butyl-1-iodo-2-methylhexane

c)

1-iodo-2,4-dimethyl-3-propylhexane

d)

2,4-dimethyl-1-iodo-3-propylhexane

34.

Name the haloalkane shown.

CH3CH2C(CH3)2CH2CH2I

(a)  

35.

Name the alkane shown.

[(CH3)2CH]2CHCH3

(a)  

36.

Name the alkane shown

(a)  

37.

How many methyl groups are present in 2,4-dimethylhexane?

a)

0

b)

2

c)

4

d)

6

e)

8

38.

Identify the correct IUPAC name for the following structure.

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

e)

none of the above

39.

Identify the correct IUPAC name for each compound shown below

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

40.

Provide the name of the compound shown.v

(a)  

41.

Give structures for the three isomers with molecular formula C5H12 and provide the

common name of each

a)

1. pentane or n-pentane
2. isopentane
3. neopentane

b)

  1. 1. n-hexane or hexane

  1. 2. isohexane

  1. 3. neopentane isomer

c)

  1. 1. butane or n-butane
    2. isopentane

    1. 3. 2-methylbutane

d)

  1. 1. pentane or n-pentane

  2. 2. isopentane

  3. 3. neopentane isomer

42.

Provide an acceptable name for the alkane shown below.

(a)  

43.

Draw an acceptable structure for 4-ethyl-6-(1,2-dimethylpropyl)decane

a)

b)

c)

d)

e)

44.

Draw an acceptable structure for 1-ethyl-2-(2,2-dimethylpentyl)cyclopentane

a)

b)

c)

d)

e)

45.

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 measure

46.

A branched alkane has ________ boiling point relative to the isomeric linear alkane. There

are ________ London force interactions in the branched alkane.

a)

a higher; stronger

b)

a higher; weaker

c)

a lower, stronger

d)

a lower; weaker

e)

the same; similar

47.

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

48.

Name the following compound and use the appropriate cis/trans designation

(a)  

49.

(a)   is the n-alkane of greatest molecular weight which is a gas at room temperature

and pressure

50.

Place the following alkanes in order of increasing boiling point:

CH3(CH2)6CH3, CH3(CH2)5CH3, (CH3)3CCH2CH2CH3

(a)  

51.

Why are alkanes described as hydrophobic?

(a)  

52.

Which intermolecular force is primarily responsible for the interactions among alkane

molecules?

(a)  

53.

What is the major constituent of natural gas?

a)

octane

b)

butane

c)

propane

d)

ethane

e)

methane

54.

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

(a)  

55.

Explain why the lowest energy conformation of decane is an extended, or zig-zag

conformation.

(a)  

56.

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

57.

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—C16

58.

(a)   is the reaction process through which long-chain alkanes are converted into a

mixture of short-chain alkanes and alkenes.

59.

List three commercial products which are composed primarily of alkanes.

(a)  

60.

Linear alkanes generally have higher phase transitions than their branched isomers.

However, the melting point of cyclohexane is 6° C while the melting point of hexane is -95° C.

Briefly suggest a reason why this is.

(a)  

61.

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

(a)  

62.

By using the appropriate molecular formulas, write a balanced equation which describes the

complete combustion of cyclohexane.

(a)  

63.

When a mole of decane undergoes complete combustion, how many moles of water are

formed?

a)

1

b)

10

c)

11

d)

15.5

e)

22

64.

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

(a)  

65.

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

66.

The structures below are ________

a)

not isomers

b)

conformational isomers

c)

cis-trans isomers

d)

structural isomers

e)

both B and D

67.

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.

Draw a Newman projection of the most stable conformation of 2-methylpropane.

a)

b)

c)

d)

e)

69.

Define the term conformation.

(a)  

70.

Use a sawhorse structure to depict the eclipsed conformer of ethane

a)

b)

c)

d)

e)

71.

Draw the Newman projection of the highest energy conformation that results from rotation

about the C2-C3 bond of 2,2-dimethylbutane.

a)

b)

c)

d)

e)

72.

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.

73.

Convert the Newman structure below to the equivalent line-angle structure

a)

b)

c)

d)

e)

74.

Draw the Newman projection of the anti conformation of butane.

a)

b)

c)

d)

e)

75.

Draw the Newman projection of the highest energy conformation that results from rotation

about the C2-C3 bond of 2-methylbutane.

a)

b)

c)

d)

e)

76.

Consider rotation about the C3-C4 bond of hexane, and draw the Newman projection for the

most stable conformation.

a)

b)

c)

d)

e)

77.

Arrange the following conformers of butane in order of energy, lowest to highest: eclipsed,

totally eclipsed, gauche, and anti

(a)  

78.

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

79.

Which line angle drawing best represents the Newman Projection shown below?

a)

b)

c)

d)

80.

Without any change in conformation, translate the Newman projection shown below to a

perspective structure

a)

b)

c)

d)

e)

81.

View a butane molecule along the C2—C3 bond and provide a Newman projection of the

lowest energy conformer.

a)

b)

c)

d)

e)

82.

Provide a Newman Projection of the gauche conformer of butane

a)

b)

c)

d)

e)

83.

From the perspective of viewing down the C2—C3 bond, draw the Newman projection of

the most stable conformation of 2,3-dimethylbutane.

a)

b)

c)

d)

e)

84.

From the perspective of viewing down the C2-C3 bond, draw the Newman projection of the

least stable conformation of 2,3-dimethylbutane.

a)

b)

c)

d)

e)

85.

In a Newman projection, siting down the C3-C4 bond, draw the structure below in its most

stable conformation.

a)

b)

c)

d)

e)

86.

If a monocyclic 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

87.

Give the IUPAC name for the cycloalkane shown below

(a)  

88.

Give the IUPAC name for the cycloalkane shown below

(a)  

89.

What element of ring strain exists in cyclooctane but not in cyclopropane?

(a)  

90.

Provide an acceptable name for the following compound.

(a)  

91.

Provide the name of the compound below

(a)  

92.

Identify the correct IUPAC name for the structure shown below.

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

93.

Given the following heats of combustion per CH2 group within the structure, which cyclic

alkane has essentially no angle strain? (Ref: long-chain Alkane = 659 kJ/mol)

a)

cyclobutane = 686 kJ/mol

b)

cyclopentane = 664 kJ/mol

c)

cyclohexane = 659 kJ/mol

d)

cycloheptane = 662 kJ/mol

e)

cyclooctane = 663 kJ/mol

94.

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

a)

cyclooctane

b)

cycloheptane

c)

cyclohexane

d)

cyclobutane

e)

cyclopropane

95.

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

96.

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

a)

cyclopropane

b)

cyclobutane

c)

cyclopentane

d)

cyclohexane

e)

cycloheptane

97.

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

98.

Which has the greatest molar heat of combustion?

a)

trans-1,2-dimethylcyclopentane

b)

cis-1,2-dimethylcyclopentane

c)

trans-1,3-dimethylcyclopentane

d)

methylcyclohexane

e)

cycloheptane

99.

Describe the sources of angle strain and torsional strain present in cyclopropane

(a)  

100.

The twisted boat conformation of cyclohexane is actually a slightly lower energy

conformation than the boat conformation. Which of the following accurately describes one

factor involved in this structural behavior?

a)

lower angle strain in the boat

b)

higher torsional strain in the twisted boat

c)

fewer unfavorable steric factors in the twisted boat

d)

increased rotational freedom in the boat

e)

lower bond strain in the boat

101.

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

equatorial hydrogens (He).

a)

b)

c)

d)

e)

102.

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

e)

none of the above

103.

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

104.

Consider the equilibrium shown below. When one looks at the equilibrium where X = CH3

and the one where X = CH(CH3)2, how do the values of the equilibrium constants (Ks)

compare?

a)

The Ks are equal.

b)

The K where X = CH3 is greater.

c)

The K where X = CH(CH3)2 is greater.

d)

The Ks differ only slightly and are both less than 1.

105.

Draw isopropylcyclohexane in a chair conformation and then draw its ring flipped isomer.

Label the substituent as either axial or equitorial. Indicate which of the conformers is more

stable

a)

b)

c)

d)

e)

106.

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

107.

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.

108.

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.

109.

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

110.

In the lowest energy conformation of the compound below, how many alkyl substituents are

equatorial?

a)

0

b)

1

c)

2

d)

3

e)

6

111.

In the lowest energy conformation of the compound below, how many alkyl substituents are

axial?

a)

0

b)

1

c)

2

d)

3

e)

6

112.

Assuming a chair conformation, which of the following configurations will always have

both methyl groups in relative axial/equatorial positions?

a)

trans-1,3-dimethylcyclohexane

b)

cis-1,3-dimethylcyclohexane

c)

cis-1,2-dimethylcyclohexane

d)

trans-1,2-dimethylcyclohexane

e)

Both A and C are correct.

113.

Draw the most stable conformation of cis-1-t-butyl-4-methylcyclohexane.

a)

b)

c)

d)

e)

114.

Draw the chair conformation of the cyclohexane derivative shown.

a)

b)

c)

d)

e)

115.

Draw the most stable conformation of cis-1,4-dipropylcyclohexane

a)

b)

c)

d)

e)

116.

Draw the most stable conformation of trans-1,4-dipropylcyclohexane

a)

b)

c)

d)

e)

117.

Draw the most stable conformation of trans-1,2-dimethylcyclohexane

a)

b)

c)

d)

e)

118.

Draw the most stable conformation of cis-1,2-dimethylcyclohexane

a)

b)

c)

d)

e)

119.

Draw the most stable conformation of trans-1-tert-butyl-3-ethylcyclohexane

a)

b)

c)

d)

e)

120.

Draw the most stable conformation of cis-1-ethyl-3-methylcyclohexane.

a)

b)

c)

d)

e)

121.

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

a)

cis 1,2-difluorocyclohexane

b)

trans 1,2-difluorocyclohexane

c)

cis 1,3-difluorocyclohexane

d)

trans 1,3-difluorocyclohexane

122.

Draw the most stable conformation of cis-1-ethyl-4-isopropylcyclohexane

a)

b)

c)

d)

e)

123.

Which of the following correctly lists the conformations of cis-1,4-di-t-butylcylcohexane in

order of increasing energy?

a)

chair < boat < twist boat < half-chair

b)

twist boat < boat < chair < half-chair

c)

chair < twist boat < half-chair < boat

d)

boat < chair < twisted boat < half-chair

e)

half-chair < chair < boat < twisted boat

124.

With each structure below drawn in its most stable chair conformation, identify the

sequence that ranks the structures in order of increasing stability

a)

1 < 2 < 3

b)

2 < 3 < 1

c)

3 < 1 < 2

d)

2 < 1 < 3

125.

Circle all substituents that would be expected to occupy an axial position in the fused

bicyclic structure below.

a)

b)

c)

d)

e)

126.

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

e)

none of the above

127.

Which of the following describes the compound below?

a)

bridged bicyclic

b)

fused bicyclic

c)

spiro bicyclic

d)

bridged tricyclic

128.

Provide an acceptable name for the compound below.

(a)  

129.

Provide an acceptable structure for spiro [4.4]nonane

a)

b)

c)

d)

e)

130.

Draw the most stable conformation of trans-decalin.

a)

b)

c)

d)

e)

131.

Arrange the following Newman projections of butane in order of energy.

a)

I<III<II<IV

b)

IV<II<III<I

c)

III<I<IV<II

d)

II<IV<I<III

132.

Which line-angle formula corresponds to the chair conformation shown below?

a)

I

b)

II

c)

III

d)

IV

133.

Draw a Newman Projection along the C3-C4 for the molecule shown below. (C3 should be

in front.)

a)

b)

c)

d)

e)

134.

Draw a Newman Projection along the C3-C4 for the molecule shown below. (C3 should be

in front.)

a)

b)

c)

d)

e)

135.

The structures below are the same

a)

True

b)

False

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