Organic Chemistry 8th Edition By L. G. Wade – Test Bank
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Sample Test
Organic Chemistry, 8e (Wade)
Chapter 3 Structure and Stereochemistry of Alkanes
1) Which of the statements below accurately describe(s) alkanes?
1. A)
Alkanes are hydrocarbons which contain only single bonds.
2. B)
Alkanes belong to the class of unsaturated hydrocarbons.
3. C)
Alkanes are the simplest and least reactive class of organic compounds.
4. D)
both A and B
5. E)
both A and C
Answer: E
Diff: 1
Section: 3.1
2) Which of the following types of hydrocarbons is(are)
saturated?
1. A)
alkanes
2. B)
alkenes
3. C)
alkynes
4. D)
aromatics
5. E)
All of the above are saturated.
Answer: A
Diff: 1
Section: 3.1
3) If a hydrocarbon has no double or triple bonds, it is said to
be ________.
Answer: saturated
Diff: 1
Section: 3.1
4) Straight-chain alkanes are also called ________.
Answer: n-alkanes
Diff: 2
Section: 3.1
5) The structure below is a potent analgesic agent (pain
reliever) (J. Med. Chem., 2009, 5685). How many secondary carbons are in
this structure?
1. A) 2
2. B) 4
3. C) 6
4. D) 12
Answer: A
Diff: 2
Section: 3.1
6) If an acyclic alkane hydrocarbon contains n carbon atoms, how
many hydrogen atoms must it also contain?
1. A) n
2. B) 2n
3. C) n
+ 2
4. D) 2n
+ 2
5. E) n
– 2
Answer: D
Diff: 2
Section: 3.2
7) A series of compounds, like the n-alkanes, that differ only
by the number of -CH2- groups, is called a(n) ________ series.
Answer: homologous
Diff: 2
Section: 3.2
8) A bicyclic alkane contains 12 carbon atoms. How many hydrogen
atoms does it contain?
1. A) 20
2. B) 22
3. C) 24
4. D) 26
5. E) 28
Answer: B
Diff: 2
Section: 3.2
9) How many methylene groups are present in 2,4-dimethylhexane?
1. A) 0
2. B) 1
3. C) 2
4. D) 6
5. E) 8
Answer: C
Diff: 2
Section: 3.2
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?
1. A) 30
2. B) 32
3. C) 58
4. D) 60
5. E) 62
Answer: E
Diff: 3
Section: 3.2
11) How many secondary (2°) carbons are found in
5-ethyl-3,3,4-trimethylheptane?
1. A) 1
2. B) 4
3. C) 2
4. D) 3
5. E) 6
Answer: D
Diff: 1
Section: 3.3
12) Provide an acceptable name for (CH3CH2CH2)3CH.
Answer: 4-propylheptane
Diff: 1
Section: 3.3
13) Provide the name of the compound below.
Answer: 3-fluoro-2,2-dimethylhexane
Diff: 1
Section: 3.3
14) Provide the name of the compound below.
Answer: 2,3,6,7-tetramethylnonane
Diff: 1
Section: 3.3
15) Provide an acceptable name for the alkane shown below.
CH3CH2CH2CH2CH2CH3
Answer: hexane or n-hexane
Diff: 1
Section: 3.3
16) Provide an acceptable name for the alkane shown below.
Answer: 2,5-dimethylheptane
Diff: 1
Section: 3.3
17) Draw an acceptable structure for 4-tert-butyloctane.
Answer:
Diff: 1
Section: 3.3
18) Draw an acceptable structure for 3-ethyl-3-methylhexane.
Answer:
Diff: 1
Section: 3.3
19) Draw an acceptable structure for
4-isopropyl-2-methylheptane.
Answer:
Diff: 1
Section: 3.3
20) Name the haloalkane shown.
Answer: 3,4-dibromoheptane
Diff: 1
Section: 3.3
21) Provide an acceptable name for the following compound.
Answer: 4,4-dichloro-6-isopropyl-3-methylnonane
Diff: 2
Section: 3.3
22) Provide an acceptable name for the [(CH3)3C]2CHCH3.
Answer: 2,2,3,4,4-pentamethylpentane
Diff: 2
Section: 3.3
23) Provide the IUPAC name of (CH3CH2)3CH.
Answer: 3-ethylpentane
Diff: 2
Section: 3.3
24) Provide the IUPAC name of (CH3)2CHCH2CH2C(CH3)3.
Answer: 2,2,5-trimethylhexane
Diff: 2
Section: 3.3
25) Predict the molecular formula of
4-ethyl-5,5-dimethyldodecane.
Answer: C16H34
Diff: 2
Section: 3.3
26) Provide an acceptable name for the alkane shown below.
Answer: 5-sec-butyl-2,2-dimethylnonane or
2,2-dimethyl-5-(1-methylpropyl)nonane
Diff: 2
Section: 3.3
27) Provide an acceptable name for the alkane shown below.
Answer: 4-isopropyldecane or
4-(1-methylethyl)decane
Diff: 2
Section: 3.3
28) Provide an acceptable name for the alkane shown below.
Answer: 3-ethyl-4,4-dimethylheptane
Diff: 2
Section: 3.3
29) Draw an acceptable structure for
6-ethyl-2,6,7-trimethyl-5-propylnonane.
Answer:
Diff: 2
Section: 3.3
30) Provide an acceptable name for the alkane shown below.
Answer: 2,2,3,6-tetramethylheptane
Diff: 2
Section: 3.3
31) Provide an acceptable name for the alkane shown below.
Answer: 6-ethyl-2-methyl-5-propyldecane
Diff: 2
Section: 3.3
32) Provide an acceptable name for the alkane shown below.
Answer: 5-ethyl-2,2-dimethylheptane
Diff: 2
Section: 3.3
33) Identify the correct IUPAC name for the following
structures.
1. A)
4-(2-iodo-1-methylethyl)-3-methylheptane
2. B)
3-s-butyl-1-iodo-2-methylhexane
3. C)
1-iodo-2,4-dimethyl-3-propylhexane
4. D)
2,4-dimethyl-1-iodo-3-propylhexane
Answer: A
Diff: 2
Section: 3.3
34) Name the haloalkane shown.
CH3CH2C(CH3)2CH2CH2I
Answer: 1-iodo-3,3-dimethylpentane
Diff: 2
Section: 3.3
35) Name the alkane shown.
[(CH3)2CH]2CHCH3
Answer: 2,3,4-trimethylpentane
Diff: 2
Section: 3.3
36) Name the alkane shown.
Answer: 5-ethyl-2,2-dimethyloctane
Diff: 2
Section: 3.3
37) How many methyl groups are present in 2,4-dimetylhexane?
1. A) 0
2. B) 2
3. C) 4
4. D) 6
5. E) 8
Answer: C
Diff: 2
Section: 3.3
38) Identify the correct IUPAC name for the following structure.
1. A)
6-bromo-1-cyclopentyl-3,6-dimethylhexane
2. B)
1-bromo-5-cyclopentyl-1,4-dimethylpentane
3. C)
2-bromo-6-cyclopentyl-5-methylhexane
4. D)
5-bromo-1-cyclopentyl-2-methylhexane
5. E)
none of the above
Answer: D
Diff: 3
Section: 3.3
39) Identify the correct IUPAC name for each compound shown
below.
1. A)
2-bromo-3-sec-butyl-4-ethylhexane
2. B)
2-bromo-4-ethyl-3-sec-butylhexane
3. C) 3-(1-bromoethyl)-2,4-diethylhexane
4. D)
4-(1-bromoethyl)-3-ethyl-5-methylheptane
5. E)
4-(1-bromoethyl)-5-ethyl-3-methylheptane
Answer: D
Diff: 3
Section: 3.3
40) Provide the name of the compound shown.
Answer: 2,2,7-trichloro-4-ethyl-6-isobutyl-7,10-dimethyldodecane
Diff: 3
Section: 3.3
41) Give structures for the three isomers with molecular formula
C5H12 and provide the common name of each.
Answer:
Diff: 3
Section: 3.3
42) Provide an acceptable name for the alkane shown below.
Answer: 3-ethyl-7-methyl-5-propylnonane
Diff: 3
Section: 3.3
43) Draw an acceptable structure for
4-ethyl-6-(1,2-dimethylpropyl)decane.
Answer:
Diff: 3
Section: 3.3
44) Draw an acceptable structure for
1-ethyl-2-(2,2-dimethylpentyl)cyclopentane.
Answer:
Diff: 3
Section: 3.3
45) When one compares the densities of n-hexane and water, one
finds:
1. A)
that n-hexane is less dense than water.
2. B)
that n-hexane is more dense than water.
3. C)
that these two compounds have the same density.
4. D)
that the relative densities of two immiscible compounds cannot be measured.
Answer: A
Diff: 1
Section: 3.4
46) A branched alkane has ________ boiling point relative to the
isomeric linear alkane. There are ________ London force interactions in
the branched alkane
1. A) a
higher; stronger
2. B) a
higher; weaker
3. C) a
lower, stronger
4. D) a
lower; weaker
5. E)
the same; similar
Answer: D
Diff: 1
Section: 3.4
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?
1. A)
2,3-dimethylbutane < 2-methylpentane < n-hexane
2. B)
2-methylpentane < n-hexane < 2,3-dimethylbutane
3. C)
2-methylpentane < 2,3-dimethylbutane < n-hexane
4. D)
n-hexane < 2-methylpentane < 2,3-dimethylbutane
5. E)
n-hexane < 2,3-dimethylbutane < 2-methylpentane
Answer: A
Diff: 2
Section: 3.4
48) A branched alkane generally melts at a ________ temperature
than the n-alkane containing the same number of carbons.
Answer: lower
Diff: 2
Section: 3.4
49) ________ is the n-alkane of greatest molecular weight which
is a gas at room temperature and pressure.
Answer: Butane
Diff: 2
Section: 3.4
50) Place the following alkanes in order of increasing boiling
point:
CH3(CH2)6CH3, CH3(CH2)5CH3, (CH3)3CCH2CH2CH3
Answer: (CH3)3CCH2CH2CH3 <
CH3(CH2)5CH3 < CH3(CH2)6CH3
Diff: 2
Section: 3.4
51) Why are alkanes described as hydrophobic?
Answer: Alkanes are nonpolar and as such they do not
dissolve to any appreciable extent in water.
Diff: 2
Section: 3.4
52) Which intermolecular force is primarily responsible for the
interactions among alkane molecules?
Answer: van der Waals or London
forces
Diff: 2
Section: 3.4
53) What is the major constituent of natural gas?
1. A) octane
2. B)
butane
3. C)
propane
4. D)
ethane
5. E)
methane
Answer: E
Diff: 1
Section: 3.5
54) Within the context of commercial uses of alkanes, explain
what “knocking” is.
Answer: “Knocking” is the potentially damaging, premature
explosive combustion of certain gasoline mixtures in a car’s engine.
Diff: 1
Section: 3.5
55) Natural gas is primarily composed of
1. A)
oxygen.
2. B)
carbon dioxide.
3. C)
methane.
4. D)
octane.
5. E)
ethanol.
Answer: C
Diff: 1
Section: 3.5
56) Which alkanes have largely replaced Freons as propellants in
aerosol cans?
1. A)
methane and ethane
2. B)
propane and butane
3. C)
pentane and hexane
4. D)
nonane and decane
5. E)
none of the above
Answer: B
Diff: 2
Section: 3.5
57) How many carbons do the primary alkane constituents of
gasoline contain?
1. A) C1C2
2. B)
C3C4
3. C)
C5C8
4. D)
C8C12
5. E)
C12C16
Answer: C
Diff: 2
Section: 3.5
58) ________ is the reaction process through which long-chain
alkanes are converted into a mixture of short-chain alkanes and alkenes.
Answer: Catalytic cracking
Diff: 2
Section: 3.5
59) List three commercial products which are composed primarily
of alkanes.
Answer: natural gas, gasoline, kerosene, heating oil,
lubricating oil, liquefied petroleum gas, jet fuel, diesel oil, petroleum jelly
Diff: 2
Section: 3.5
60) Name the two major steps in the refining of crude oil into
usable hydrocarbon products.
Answer: 1. fractional distillation
2. cracking
(catalytic cracking and/or hydrocracking)
Diff: 2
Section: 3.5
61) In the complete combustion of heptane, how many moles of water
are produced?
Answer: 8
Diff: 2
Section: 3.6
62) By using the appropriate molecular formulas, write a
balanced equation which describes the complete combustion of cyclohexane.
Answer: C6H12 + 9 O2 → 6 CO2
+ 6 H2O
Diff: 2
Section: 3.6
63) When a mole of decane undergoes complete combustion, how
many moles of water are formed?
1. A) 1
2. B) 10
3. C) 11
4. D)
15.5
5. E) 22
Answer: C
Diff: 2
Section: 3.6
64) By using the appropriate molecular formulas, write a
balanced equation which describes the complete combustion of nonane.
Answer: CH3(CH2)7CH3 + 14 O2 → 9
CO2 + 10 H2O
Diff: 3
Section: 3.6
65) The energy barrier for carbon-carbon bond rotation in
propane is mainly due to ________.
1. A)
angle strain
2. B)
bond strain
3. C)
muscle strain
4. D) steric
strain
5. E)
torsion strain
Answer: E
Diff: 1
Section: 3.7
66) The structures below are:
1. A)
not isomers.
2. B)
conformational isomers.
3. C)
cis-trans isomers.
4. D)
structural isomers.
5. E)
both B and D
Answer: D
Diff: 2
Section: 3.7
67) Which of the following best describes the molecules of a
sample of ethane gas at room temperature?
1. A)
Almost all of the molecules are frozen or locked in the eclipsed conformation.
2. B)
Almost all of the molecules are frozen or locked in the staggered conformation.
3. 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.
4. 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.
Answer: D
Diff: 2
Section: 3.7
68) Draw a Newman projection of the most stable conformation of
2-methylpropane.
Answer:
Diff: 2
Section: 3.7
69) Define the term conformation.
Answer: Conformations are different arrangements of the
same molecule formed by rotations about single bonds.
Diff: 2
Section: 3.7
70) Use a sawhorse structure to depict the eclipsed conformer of
ethane.
Answer:
Diff: 2
Section: 3.7
71) Draw the Newman projection of the highest energy
conformation that results from rotation about the C2-C3 bond of
2,2-dimethylbutane.
Answer:
Diff: 1
Section: 3.8
72) Which of the following statements concerning the conformers
of butane is true?
1. A)
Unlike ethane, all butane conformers are classified as eclipsed.
2. B)
The lowest energy conformer of butane is the gauche conformer.
3. C)
There is more torsional strain in the anti conformer than in the totally
eclipsed conformer.
4. D) The
eclipsed and totally eclipsed conformers have the same amount of nonbonded
strain.
5. E)
The gauche and anti conformers differ primarily in the amount of nonbonded
strain present.
Answer: E
Diff: 2
Section: 3.8
73) Draw the Newman projection of the lowest energy conformation
that results from rotation about the C2-C3 bond of 2-methylbutane.
Answer:
Diff: 2
Section: 3.8
74) Draw the Newman projection of the lowest energy conformation
that results from rotation about the C2-C3 bond of 2,2-dimethylbutane.
Answer:
Diff: 2
Section: 3.8
75) Draw the Newman projection of the highest energy
conformation that results from rotation about the C2-C3 bond of 2-methylbutane.
Answer:
Diff: 2
Section: 3.8
76) Consider rotation about the C3-C4 bond of hexane, and draw
the Newman projection for the most stable conformation.
Answer:
Diff: 2
Section: 3.8
77) Arrange the following conformers of butane in order of
energy, lowest to highest: eclipsed, totally eclipsed, gauche, and anti.
Answer: anti < gauche < eclipsed < totally
eclipsed
Diff: 2
Section: 3.8
78) Among the butane conformers, which occur at energy minima on
a graph of potential energy versus dihedral angle?
1. A)
gauche only
2. B)
eclipsed and totally eclipsed
3. C)
gauche and anti
4. D)
eclipsed only
5. E)
anti only
Answer: C
Diff: 3
Section: 3.8
79) For the compound represented by the Newman projection below,
what is the dihedral angle between the methyl groups in the conformer that has
the smallest molecular dipole moment?
1. A) 0°
2. B)
30°
3. C)
60°
4. D)
120°
5. E)
180°
Answer: C
Diff: 3
Section: 3.8
80) Without any change in conformation, translate the Newman
projection shown below to a perspective structure.
Answer:
Diff: 3
Section: 3.8
81) View a butane molecule along the C2C3 bond and provide a
Newman projection of the lowest energy conformer.
Answer:
Diff: 3
Section: 3.8
82) Provide a representation of the gauche conformer of butane.
Answer:
Diff: 3
Section: 3.8
83) From the perspective of viewing down the C2C3 bond, draw
the Newman projection of the most stable conformation of 2,3-dimethylbutane.
Answer:
Diff: 3
Section: 3.8
84) From the perspective of viewing down the C2-C3 bond, draw
the Newman projection of the least stable conformation of 2,3-dimethylbutane.
Answer:
Diff: 3
Section: 3.8
85) In a Newman projection, siting down the C3-C4 bond, draw the
structure below in its most stable conformation.
Answer:
Diff: 3
Section: 3.9
86) If a monocyclic alkane hydrocarbon contains n carbon atoms,
how many hydrogen atoms must it also contain?
1. A) n
2. B) 2n
3. C) n
+ 2
4. D) 2n
+ 2
5. E) n
– 2
Answer: B
Diff: 1
Section: 3.10
87) Give the IUPAC name for the cycloalkane shown below.
Answer: trans-1-ethyl-2-methylcyclopentane
Diff: 1
Section: 3.10
88) Give the IUPAC name for the cycloalkane shown below.
Answer: cis-1-isopropyl-3-methylcycloheptane
Diff: 1
Section: 3.10
89) What element of ring strain exists in cyclooctane but not in
cyclopropane?
Answer: transannular strain
Diff: 1
Section: 3.10
90) Provide an acceptable name for the following compound.
Answer: isobutylcyclopentane or
(2-methylpropyl)cyclopentane
Diff: 2
Section: 3.10
91) Provide the name of the compound below.
Answer: sec-butylcycloheptane
Diff: 2
Section: 3.10
92) Identify the correct IUPAC name for the structure shown
below.
1. A)
1-tert-butyl-2-chloro-5-bromocycloheptane
2. B)
5-bromo-1-tert-butyl-2-chlorocycloheptane
3. C)
1-bromo-4-chloro-5-tertbutylcycloheptane
4. D)
1-bromo-4-tert-butyl-5-chlorocycloheptane
5. E)
1-tert-butyl-4-bromo-7-chlorocycloheptane
Answer: B
Diff: 3
Section: 3.10
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)
1. A)
cyclobutane = 686 kJ/mol
2. B)
cyclopentane = 664 kJ/mol
3. C)
cyclohexane = 659 kJ/mol
4. D)
cycloheptane = 662 kJ/mol
5. E)
cyclooctane = 663 kJ/mol
Answer: C
Diff: 1
Section: 3.12
94) Which of the following cycloalkanes exhibits the greatest
molar heat of combustion?
1. A)
cyclooctane
2. B)
cycloheptane
3. C)
cyclohexane
4. D)
cyclobutane
5. E)
cyclopropane
Answer: A
Diff: 2
Section: 3.12
95) Which of the following correctly ranks the cycloalkanes in
order of increasing ring strain per methylene?
1. A)
cyclopropane < cyclobutane < cyclohexane < cyclopentane
2. B)
cyclohexane < cyclopentane < cyclobutane < cyclopropane
3. C)
cyclohexane < cyclobutane < cyclopentane < cyclopropane
4. D)
cyclopentane < cyclopropane < cyclobutane < cyclohexane
5. E)
cyclopropane < cyclopentane < cyclobutane < cyclohexane
Answer: B
Diff: 2
Section: 3.12
96) Which of the following cycloalkanes has the smallest heat of
combustion per CH2 group?
1. A)
cyclopropane
2. B)
cyclobutane
3. C)
cyclopentane
4. D)
cyclohexane
5. E)
cycloheptane
Answer: D
Diff: 2
Section: 3.12
97) Which of the following statements regarding cyclobutane is
correct?
1. A)
The lowest energy conformation of cyclobutane is a planar one in which all of
the bond angles is 90°.
2. B)
The lowest energy conformation of cyclobutane is known as the chair
conformation.
3. C)
The lowest energy conformation is one in which the bond angles are slightly
less than 90° even though this increases angle strain.
4. D)
The lowest energy conformation is one in which the bond angles are greater than
90° so that angle strain is significantly reduced.
5. E)
None of the above statements is correct.
Answer: C
Diff: 3
Section: 3.12
98) Which has the greatest molar heat of combustion?
1. A)
trans-1,2-dimethylcyclopentane
2. B)
cis-1,2-dimethylcyclopentane
3. C)
trans-1,3-dimethylcyclopentane
4. D)
methylcyclohexane
5. E)
cycloheptane
Answer: B
Diff: 3
Section: 3.12
99) Describe the sources of angle strain and torsional strain
present in cyclopropane.
Answer: 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 CH bonds on adjacent carbons are eclipsed.
Diff: 3
Section: 3.12
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 ?
1. A)
lower angle strain in the boat
2. B)
higher torsional strain in the twisted boat
3. C)
fewer unfavorable steric factors in the twisted boat
4. D)
increased rotational freedom in the boat
5. E)
lower bond strain in the boat
Answer: C
Diff: 1
Section: 3.13
101) Draw the chair conformer of cyclohexane. Label the axial
hydrogens (Ha) and the equatorial hydrogens (He).
Answer:
Diff: 1
Section: 3.13
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