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)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
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 C5 H12 and provide the common name of each.
7) Provide an acceptable name for the alkane shown below.
CH3 CH2CH2 CH2 CH2 CH3
8) Provide an acceptable name for the alkane shown below.
9) Provide an acceptable name for the alkane shown below.
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10) Provide an acceptable name for the alkane shown below.
11) Provide an acceptable name for the alkane shown below.
12) Provide an acceptable name for the alkane shown below.
13) Draw an acceptable structure for 4-tert-butyloctane.
14) Draw an acceptable structure for 4-ethyl-6-(1,2-dimethylpropyl)decane.
15) Draw an acceptable structure for 1-ethyl-2-(2,2-dimethylpentyl)cyclopentane.
16) Draw an acceptable structure for 3-ethyl-3-methylhexane.
17) Draw an acceptable structure for 4-isopropyl-2-methylheptane.
18) Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane.
19) Provide an acceptable name for the alkane shown below.
20) Provide an acceptable name for the alkane shown below.
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21) List three commercial products which are composed primarily of alkanes.
22) Why are alkanes described as hydrophobic?
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
24) Which intermolecular force is primarily responsible for the interactions among alkane molecules?
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
26) A branched alkane generally melts at a __________ temperature than the n-alkane
containing the same number of carbons.
26)
27) __________ is the n-alkane of greatest molecular weight which is a gas at room
temperature and pressure.
27)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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
29) How many carbons do the primary alkane constituents of gasoline contain?
A) C1 C2
B) C3 C4
C) C5C8
D) C8 C12
28)
29)
E) C12C16
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
30) Name the two major steps in the refining of crude oil into usable hydrocarbon products.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
31) What is the major constituent of natural gas?
A) octane
B) butane
C) propane
31)
D) ethane
E) methane
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
32) By using the appropriate molecular formulas, write a balanced equation which describes the complete
combustion of nonane.
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
33) __________ is the reaction process through which long-chain alkanes are converted into a
mixture of short-chain alkanes and alkenes.
33)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
34) Draw a Newman projection of the most stable conformation of 2-methylpropane.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
35) The structures below are:
35)
A) not isomers.
B) conformational isomers.
C) cis-trans isomers.
D) structural isomers.
E) both B and D
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
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.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
41) Give the IUPAC name for the cycloalkane shown below.
42) Give the IUPAC name for the cycloalkane shown below.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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) 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
44)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
45) Describe the sources of angle strain and torsional strain present in cyclopropane.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
47) Draw the most stable conformation of trans-1,2-dimethylcyclohexane.
48) Draw the most stable conformation of cis-1,2-dimethylcyclohexane.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
51) Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha ) and the equatorial hydrogens (He).
52) Draw the most stable conformation of trans-1-tert-butyl-3-ethylcyclohexane.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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
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53)
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.
E) none of the above
54)
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
55)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
56) Draw the most stable conformation of cis-1-ethyl-3-methylcyclohexane.
57) Draw the most stable conformation of cis-1-ethyl-4-isopropylcyclohexane.
58) Provide an acceptable structure for spiro [4.4]nonane.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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
E) none of the above
59)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
60) Provide an acceptable name for the compound below.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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
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61)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
62) Provide an acceptable name for the alkane shown below.
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
63) A series of compounds, like the n-alkanes, that differ only by the number of CH2 
63)
groups, is called a(n) __________ series.
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
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.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
70) Draw the most stable conformation of trans-decalin.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
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 )3 C]2 CHCH3.
74)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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.
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
76) Arrange the following conformers of butane in order of energy, lowest to highest: eclipsed,
totally eclipsed, gauche, and anti.
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76)
75)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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?
A) 0
B) 1
C) 2
D) 3
E) 6
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
80) Provide an acceptable name for (CH3 CH2CH2 )3 CH.
80)
81) Draw the most stable conformation of cis-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)
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79)
86) In the complete combustion of heptane, how many moles of water are produced?
86)
87) Provide the IUPAC name of (CH3 CH2)3 CH.
87)
88) Provide the IUPAC name of (CH3 )2CHCH2 CH2 C(CH3 )3 .
88)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
89) Which of the following cycloalkanes has the smallest heat of combustion per CH2 group?
89)
A) cyclopropane
B) cyclobutane
C) cyclopentane
D) cyclohexane
E) cycloheptane
90) 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
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
E) none of the above
92) 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
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92)
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?
A) bridged bicyclic
C) spiro bicyclic
94)
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
95)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
Use the following Newman projection for the question(s) below.
96) Without any change in conformation, translate the Newman projection shown above to a
perspective structure.
96)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
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
B) trans 1,2-difluorocyclohexane
C) cis 1,3-difluorocyclohexane
D) trans 1,3-difluorocyclohexane
98)
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Answer Key
Testname: UNTITLED7
1) E
ID: oc6w 3-1
Diff: 1
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2) saturated
ID: oc6w 3-2
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3) D
ID: oc6w 3-3
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4) n-alkanes
ID: oc6w 3-4
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5) C16H34
ID: oc6w 3-5
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6)
ID: oc6w 3-6
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7) hexane or n-hexane
ID: oc6w 3-7
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8) 2,5-dimethylheptane
ID: oc6w 3-8
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9) 5-sec-butyl-2,2-dimethylnonane or 2,2-dimethyl-5-(1-methylpropyl)nonane
ID: oc6w 3-9
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10) 4-isopropyldecane or 4-(1-methylethyl)decane
ID: oc6w 3-10
Diff: 2
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11) 3-ethyl-7-methyl-5-propylnonane
ID: oc6w 3-11
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Answer Key
Testname: UNTITLED7
12) 3-ethyl-4,4-dimethylheptane
ID: oc6w 3-12
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13)
ID: oc6w 3-13
Diff: 1
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14)
ID: oc6w 3-14
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15)
ID: oc6w 3-15
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16)
ID: oc6w 3-16
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17)
ID: oc6w 3-17
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Answer Key
Testname: UNTITLED7
18)
ID: oc6w 3-18
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19) 2,2,3,6-tetramethylheptane
ID: oc6w 3-19
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20) 6-ethyl-2-methyl-5-propyldecane
ID: oc6w 3-20
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21) natural gas, gasoline, kerosene, heating oil, lubricating oil, liquefied petroleum gas, jet fuel, diesel oil, petroleum jelly
ID: oc6w 3-21
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22) Alkanes are nonpolar and as such they do not dissolve to any appreciable extent in water.
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23) A
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24) van der Waals or London forces
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25) A
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26) higher
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27) Butane
ID: oc6w 3-27
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28) B
ID: oc6w 3-28
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Answer Key
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29) C
ID: oc6w 3-29
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30) 1. fractional distillation
2. cracking (catalytic cracking and/or hydrocracking)
ID: oc6w 3-30
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31) E
ID: oc6w 3-31
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32) CH3 (CH2)7 CH3 + 14 O2 → 9 CO2 + 10 H2 O
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33) Catalytic cracking
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34)
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35) D
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36) Conformations are different arrangements of the same molecule formed by rotations about single bonds.
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37)
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Answer Key
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38)
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39)
ID: oc6w 3-39
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40) C
ID: oc6w 3-40
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41) trans-1-ethyl-2-methylcyclopentane
ID: oc6w 3-41
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42) cis-1-isopropyl-3-methylcycloheptane
ID: oc6w 3-42
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43) A
ID: oc6w 3-43
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44) B
ID: oc6w 3-44
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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
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46) A
ID: oc6w 3-46
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Answer Key
Testname: UNTITLED7
47)
ID: oc6w 3-47
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48)
ID: oc6w 3-48
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49) D
ID: oc6w 3-49
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50) A
ID: oc6w 3-50
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51)
ID: oc6w 3-51
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52)
ID: oc6w 3-52
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53) D
ID: oc6w 3-53
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54) D
ID: oc6w 3-54
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Answer Key
Testname: UNTITLED7
55) C
ID: oc6w 3-55
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56)
ID: oc6w 3-56
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57)
ID: oc6w 3-57
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58)
ID: oc6w 3-58
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59) B
ID: oc6w 3-59
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60) Bicyclo[2.1.1]hexane
ID: oc6w 3-60
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61) B
ID: oc6w 3-61
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62) 5-ethyl-2,2-dimethylheptane
ID: oc6w 3-62
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63) homologous
ID: oc6w 3-63
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64) "Knocking" is the potentially damaging, premature explosive combustion of certain gasoline mixtures in a car's engine.
ID: oc6w 3-64
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Answer Key
Testname: UNTITLED7
65) C6 H12 + 9 O2 → 6 CO2 + 6 H2 O
ID: oc6w 3-65
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66)
ID: oc6w 3-66
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67)
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68) D
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69) E
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70)
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71) A
ID: oc6w 3-71
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Answer Key
Testname: UNTITLED7
72) 4,4-dichloro-6-isopropyl-3-methylnonane
ID: oc6w 3-72
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73) isobutylcyclopentane or 2-methylpropylcyclopentane
ID: oc6w 3-73
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74) 2,2,3,4,4-pentamethylpentane
ID: oc6w 3-74
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75) E
ID: oc6w 3-75
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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)
ID: oc6w 3-82
Diff: 1
Skill:
83)
ID: oc6w 3-83
Diff: 2
Skill:
84)
ID: oc6w 3-84
Diff: 2
Skill:
85)
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
QOI 0809 - ALKANES
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2
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3
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4
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5