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GRE-Chemistry

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G R A D U A T E R E C O R D E X A M I N A T I O N S®
Chemistry Test
Practice Book
This practice book contains
䡲 one actual, full-length GRE® Chemistry Test
䡲 test-taking strategies
Become familiar with
䡲 test structure and content
䡲 test instructions and answering procedures
Compare your practice test results with the performance of those who
took the test at a GRE administration.
This book is provided FREE with test registration by the Graduate Record Examinations Board.
www.ets.org/gre
Note to Test Takers: Keep this practice book until you receive your score report.
This book contains important information about scoring.
Copyright © 2009 by Educational Testing Service. All rights reserved.
ETS, the ETS logos, LISTENING. LEARNING. LEADING., GRADUATE RECORD EXAMINATIONS,
and GRE are registered trademarks of Educational Testing Service (ETS) in the United States and other countries.
Table of Contents
Purpose of the GRE Subject Tests ........................ 3
Development of the Subject Tests........................ 3
Content of the Chemistry Test ............................ 4
Preparing for a Subject Test.................................. 6
Test-Taking Strategies .......................................... 6
What Your Scores Mean ....................................... 7
Practice GRE Chemistry Test............................... 9
Scoring Your Subject Test .................................. 53
Evaluating Your Performance ............................. 56
Answer Sheet ..................................................... 57
Purpose of the GRE
Subject Tests
The GRE Subject Tests are designed to help graduate
school admission committees and fellowship sponsors
assess the qualifications of applicants in specific fields
of study. The tests also provide you with an assessment
of your own qualifications.
Scores on the tests are intended to indicate
knowledge of the subject matter emphasized in many
undergraduate programs as preparation for graduate
study. Because past achievement is usually a good
indicator of future performance, the scores are helpful
in predicting success in graduate study. Because
the tests are standardized, the test scores permit
comparison of students from different institutions
with different undergraduate programs. For some
Subject Tests, subscores are provided in addition to
the total score; these subscores indicate the strengths
and weaknesses of your preparation, and they may
help you plan future studies.
The GRE Board recommends that scores on the
Subject Tests be considered in conjunction with
other relevant information about applicants. Because
numerous factors influence success in graduate school,
reliance on a single measure to predict success is not
advisable. Other indicators of competence typically
include undergraduate transcripts showing courses
taken and grades earned, letters of recommendation,
and GRE General Test scores. For information about
the appropriate use of GRE scores, see the GRE Guide
to the Use of Scores at www.ets.org/gre/stupubs.
Development of the
Subject Tests
Each new edition of a Subject Test is developed by
a committee of examiners composed of professors in
the subject who are on undergraduate and graduate
faculties in different types of institutions and in
different regions of the United States and Canada.
In selecting members for each committee, the GRE
Program seeks the advice of appropriate professional
associations in the subject.
The content and scope of each test are specified
and reviewed periodically by the committee of
examiners. Test questions are written by committee
members and by other university faculty members
who are subject-matter specialists. All questions
proposed for the test are reviewed and revised by the
committee and subject-matter specialists at ETS. The
tests are assembled in accordance with the content
specifications developed by the committee to ensure
adequate coverage of the various aspects of the field
and, at the same time, to prevent overemphasis on
any single topic. The entire test is then reviewed and
approved by the committee.
Subject-matter and measurement specialists on the
ETS staff assist the committee, providing information
and advice about methods of test construction and
helping to prepare the questions and assemble the
test. In addition, each test question is reviewed to
eliminate language, symbols, or content considered
potentially offensive, inappropriate for major
subgroups of the test-taking population, or likely
to perpetuate any negative attitude that may be
conveyed to these subgroups.
CHEMISTRY TEST
PRACTICE BOOK
3
Because of the diversity of undergraduate curricula,
it is not possible for a single test to cover all the
material you may have studied. The examiners,
therefore, select questions that test the basic
knowledge and skills most important for successful
graduate study in the particular field. The committee
keeps the test up-to-date by regularly developing new
editions and revising existing editions. In this way, the
test content remains current. In addition, curriculum
surveys are conducted periodically to ensure that the
content of a test reflects what is currently being taught
in the undergraduate curriculum.
After a new edition of a Subject Test is first
administered, examinees’ responses to each test
question are analyzed in a variety of ways to determine
whether each question functioned as expected. These
analyses may reveal that a question is ambiguous,
requires knowledge beyond the scope of the test, or
is inappropriate for the total group or a particular
subgroup of examinees taking the test. Such questions
are not used in computing scores.
Following this analysis, the new test edition is
equated to an existing test edition. In the equating
process, statistical methods are used to assess the
difficulty of the new test. Then scores are adjusted so
that examinees who took a more difficult edition of
the test are not penalized, and examinees who took
an easier edition of the test do not have an advantage.
Variations in the number of questions in the different
editions of the test are also taken into account in this
process.
Scores on the Subject Tests are reported as threedigit scaled scores with the third digit always zero.
The maximum possible range for all Subject Test total
scores is from 200 to 990. The actual range of scores
for a particular Subject Test, however, may be smaller.
For Subject Tests that report subscores, the maximum
possible range is 20 to 99; however, the actual range
of subscores for any test or test edition may be smaller.
Subject Test score interpretive information is provided
in Interpreting Your GRE Scores, which you will receive
with your GRE score report. This publication is also
available at www.ets.org/gre/stupubs.
4
Content of the Chemistry Test
The test consists of about 130 multiple-choice
questions. A periodic table is printed in the test
booklet as well as a table of information (see pages
10 and 11) presenting various physical constants and
a few conversion factors among SI units. Whenever
necessary, additional values of physical constants
are printed with the text of the question. Test
questions are constructed to simplify mathematical
manipulations. As a result, neither calculators nor
tables of logarithms are needed. If the solution to a
problem requires the use of logarithms, the necessary
values are included with the question.
The content of the test emphasizes the four fields
into which chemistry has been traditionally divided
and some interrelationships among the fields. Because
of these interrelationships, individual questions may
test more than one field of chemistry. Some examinees
may associate a particular question with one field,
whereas other examinees may have encountered
the same material in a different field. For example,
the knowledge necessary to answer some questions
classified as testing organic chemistry may well have
been acquired in analytical chemistry courses by some
examinees. Consequently, the emphases of the four
fields indicated in the following outline of material
covered by the test should not be considered definitive.
I. ANALYTICAL CHEMISTRY — 15%
A. Data Acquisition and Use of Statistics —
Errors, statistical considerations
B. Solutions and Standardization —
Concentration terms, primary standards
C. Homogeneous Equilibria — Acid-base,
oxidation-reduction, complexometry
D. Heterogeneous Equilibria — Gravimetric
analysis, solubility, precipitation titrations,
chemical separations
E. Instrumental Methods — Electrochemical
methods, spectroscopic methods,
chromatographic methods, thermal
methods, calibration of instruments
F. Environmental Applications
G. Radiochemical Methods — Detectors,
applications
CHEMISTRY TEST
PRACTICE BOOK
II. INORGANIC CHEMISTRY — 25%
A. General Chemistry — Periodic trends,
oxidation states, nuclear chemistry
B. Ionic Substances — Lattice geometries,
lattice energies, ionic radii and radius/
ratio effects
C. Covalent Molecular Substances — Lewis
diagrams, molecular point groups, VSEPR
concept, valence bond description
and hybridization, molecular orbital
description, bond energies, covalent
and van der Waals radii of the elements,
intermolecular forces
D. Metals and Semiconductors — Structure,
band theory, physical and chemical
consequences of band theory
E. Concepts of Acids and Bases — BrønstedLowry approaches, Lewis theory, solvent
system approaches
F. Chemistry of the Main Group Elements
— Electronic structures, occurrences and
recovery, physical and chemical properties
of the elements and their compounds
G. Chemistry of the Transition Elements —
Electronic structures, occurrences and
recovery, physical and chemical properties
of the elements and their compounds,
coordination chemistry
H. Special Topics — Organometallic
chemistry, catalysis, bioinorganic
chemistry, applied solid-state chemistry,
environmental chemistry
III. ORGANIC CHEMISTRY — 30%
A. Structure, Bonding, and Nomenclature —
Lewis structures, orbital hybridization,
configuration and stereochemical
notation, conformational analysis,
systematic IUPAC nomenclature,
spectroscopy (IR and 1H and 13C NMR)
B. Functional Groups — Preparation,
reactions, and interconversions of
alkanes, alkenes, alkynes, dienes, alkyl
halides, alcohols, ethers, epoxides,
sulfides, thiols, aromatic compounds,
aldehydes, ketones, carboxylic acids and
their derivatives, amines
C. Reaction Mechanisms — Nucleophilic
displacements and addition, nucleophilic
aromatic substitution, electrophilic
additions, electrophilic aromatic
substitutions, eliminations, Diels-Alder
and other cycloadditions
D. Reactive Intermediates — Chemistry and
nature of carbocations, carbanions, free
radicals, carbenes, benzynes, enols
E. Organometallics — Preparation and
reactions of Grignard and organolithium
reagents, lithium organocuprates, and
other modern main group and transition
metal reagents and catalysts
F. Special Topics — Resonance, molecular
orbital theory, catalysis, acid-base
theory, carbon acidity, aromaticity,
antiaromaticity, macromolecules, lipids,
amino acids, peptides, carbohydrates,
nucleic acids, terpenes, asymmetric
synthesis, orbital symmetry, polymers
IV. PHYSICAL CHEMISTRY — 30%
A. Thermodynamics — First, second, and
third laws, thermochemistry, ideal and
real gases and solutions, Gibbs and
Helmholtz energy, chemical potential,
chemical equilibria, phase equilibria,
colligative properties, statistical
thermodynamics
B. Quantum Chemistry and Applications to
Spectroscopy — Classical experiments,
principles of quantum mechanics, atomic
and molecular structure, molecular
spectroscopy
C. Dynamics — Experimental and
theoretical chemical kinetics, solution
and liquid dynamics, photochemistry
CHEMISTRY TEST
PRACTICE BOOK
5
Preparing for a Subject Test
GRE Subject Test questions are designed to measure
skills and knowledge gained over a long period
of time. Although you might increase your scores
to some extent through preparation a few weeks
or months before you take the test, last minute
cramming is unlikely to be of further help. The
following information may be helpful.
A general review of your college courses is
probably the best preparation for the test.
However, the test covers a broad range of subject
matter, and no one is expected to be familiar
with the content of every question.
Use this practice book to become familiar with
the types of questions in the GRE Chemistry
Test, taking note of the directions. If you
understand the directions before you take the
test, you will have more time during the test to
focus on the questions themselves.
Test-Taking Strategies
The questions in the practice test in this book
illustrate the types of multiple-choice questions in
the test. When you take the actual test, you will
mark your answers on a separate machine-scorable
answer sheet. Total testing time is two hours and
fifty minutes; there are no separately timed sections.
Following are some general test-taking strategies you
may want to consider.
Read the test directions carefully, and work as
rapidly as you can without being careless. For
each question, choose the best answer from the
available options.
6
All questions are of equal value; do not waste
time pondering individual questions you find
extremely difficult or unfamiliar.
You may want to work through the test quite
rapidly, first answering only the questions about
which you feel confident, then going back and
answering questions that require more thought,
and concluding with the most difficult questions
if there is time.
If you decide to change an answer, make sure
you completely erase it and fill in the oval
corresponding to your desired answer.
Questions for which you mark no answer or
more than one answer are not counted in
scoring.
Your score will be determined by subtracting
one-fourth the number of incorrect answers
from the number of correct answers. If you have
some knowledge of a question and are able to
rule out one or more of the answer choices as
incorrect, your chances of selecting the correct
answer are improved, and answering such
questions will likely improve your score. It is
unlikely that pure guessing will raise your score;
it may lower your score.
Record all answers on your answer sheet.
Answers recorded in your test book will not be
counted.
Do not wait until the last five minutes of a
testing session to record answers on your answer
sheet.
CHEMISTRY TEST
PRACTICE BOOK
What Your Scores Mean
Your raw score — that is, the number of questions you
answered correctly minus one-fourth of the number
you answered incorrectly — is converted to the scaled
score that is reported. This conversion ensures that
a scaled score reported for any edition of a Subject
Test is comparable to the same scaled score earned
on any other edition of the same test. Thus, equal
scaled scores on a particular Subject Test indicate
essentially equal levels of performance regardless of
the test edition taken. Test scores should be compared
only with other scores on the same Subject Test. (For
example, a 680 on the Computer Science Test is not
equivalent to a 680 on the Mathematics Test.)
Before taking the test, you may find it useful
to know approximately what raw scores would be
required to obtain a certain scaled score. Several
factors influence the conversion of your raw score
to your scaled score, such as the difficulty of the test
edition and the number of test questions included in
the computation of your raw score. Based on recent
editions of the Chemistry Test, the following table
gives the range of raw scores associated with selected
scaled scores for three different test editions. (Note
that when the number of scored questions for a given
test is greater than the number of actual scaled score
points, it is likely that two or more raw scores will
convert to the same scaled score.) The three test
editions in the table that follows were selected to
reflect varying degrees of difficulty. Examinees should
note that future test editions may be somewhat more
or less difficult than the test editions illustrated in the
table.
Range of Raw Scores* Needed to Earn
Selected Scaled Scores on Three
Chemistry Test Editions That
Differ in Difficulty
Raw Scores
Scaled Score
Form A
Form B
Form C
800
96-97
95-97
94-95
700
73-74
72-73
70-72
600
50-51
48-50
47-48
500
26-28
24-25
23-24
Number of Questions Used to Compute Raw Score
129
130
130
*Raw Score = Number of correct answers minus one-fourth the
number of incorrect answers, rounded to the nearest integer.
For a particular test edition, there are many ways
to earn the same raw score. For example, on the
edition listed above as “Form A,” a raw score of 73
through 74 would earn a scaled score of 700. Below
are a few of the possible ways in which a scaled score
of 700 could be earned on that edition.
Examples of Ways to Earn a Scaled Score
of 700 on the Edition Labeled as “Form A”
Raw
Score
Questions
Answered
Correctly
Questions
Answered
Incorrectly
Questions
Not
Answered
Number of
Questions
Used to
Compute
Raw Score
73
73
0
56
129
73
79
23
27
129
73
84
44
1
129
74
74
0
55
129
74
79
21
29
129
74
85
43
1
129
CHEMISTRY TEST
PRACTICE BOOK
7
Practice Test
To become familiar with how the administration will be conducted at the test center,
first remove the answer sheet (pages 57 and 58). Then go to the back cover of the test
book (page 52) and follow the instructions for completing the identification areas of the
answer sheet. When you are ready to begin the test, note the time and begin marking
your answers on the answer sheet.
8
CHEMISTRY TEST
PRACTICE BOOK
FORM GR0627
27
GRADUATE RECORD EXAMINATIONS®
CHEMISTRY TEST
Do not break the seal
until you are told to do so.
The contents of this test are confidential.
Disclosure or reproduction of any portion
of it is prohibited.
THIS TEST BOOK MUST NOT BE TAKEN FROM THE ROOM.
Copyright © 2006 by Educational Testing Service. All rights reserved.
GRE, GRADUATE RECORD EXAMINATIONS, ETS, EDUCATIONAL TESTING
SERVICE and the ETS logos are registered trademarks of Educational Testing Service.
9
Material in the tables on pages 10 and 11 may be useful in answering the questions in this examination.
10
TABLE OF INFORMATION
Electron rest mass
me = 9.11 u 1031 kg
Proton rest mass
mp = 1.672 u 1027 kg
Neutron rest mass
mn = 1.675 u 1027 kg
Magnitude of the electron charge
e = 1.60 u 1019 C
Bohr radius
a0 = 5.29 u 1011 m
Avogadro number
NA = 6.02 u 1023 per mol
Universal gas constant
R = 8.314 J mol1 K1
= 0.0821 L ™ atm mol1 K1
= 0.08314 L ™ bar mol1 K1
Boltzmann constant
k = 1.38 u 1023 J/K
Planck constant
h = 6.63 u 1034 J ™ s
= = h/2 p = 1.05 u 1034 J ™ s
Speed of light
c = 3.00 u 108 m/s = 3.00 u 1010 cm/s
1 bar pressure
1 bar = 1.000 N m2
= 1.000 u 105 Pa
= 0.987 atm
1 atmosphere pressure
1 atm = 1.013 u 105 N m2
= 1.013 u 105 Pa
= 1.013 bar
Faraday constant
1 atomic mass unit (amu)
1 electron volt (eV)
Angstrom
Volume of 1 mol of ideal
gas at 0’ C, 1 atmosphere
Unauthorized copying or reuse of
any part of this page is illegal.
Ᏺ = 9.65 u 104 C/mol
1 amu = 1.66 u 1027 kg
1 eV = 1.602 u 1019 J
1 Å = 1010 m = 101 nm
= 22.4 L
GO ON TO THE NEXT PAGE.
11
CHEMISTRY TEST
Time— 170 minutes
130 Questions
Directions: Each of the questions or incomplete statements below is followed by five suggested answers or
completions. Select the one that is best in each case and then fill in the corresponding space on the answer sheet.
Note: Solutions are aqueous unless otherwise specified.
Throughout the test the following symbols have the specified definitions unless otherwise noted.
T
P
V
S
H
U
G
A
R
n
s
mol
C
=
=
=
=
=
=
=
=
=
=
=
=
=
temperature
pressure
volume
entropy
enthalpy
internal energy
Gibbs energy
Helmholtz energy
gas constant
number of moles
seconds
mole(s)
coulomb(s)
1. Of the following, which element has the highest
first ionization energy?
(A)
(B)
(C)
(D)
(E)
As
Ge
Ga
Rb
Sr
M
m
L
mL
g
kg
m
nm
atm
J
kJ
ppm
Pa
V
=
=
=
=
=
=
=
=
=
=
=
=
=
=
molar
molal
liter(s)
milliliter(s)
gram(s)
kilogram(s)
meter(s)
nanometer(s)
atmosphere(s)
joule(s)
kilojoule(s)
parts per million
Pascal(s)
volt(s)
2. Which of the following is the most acceptable
Lewis electron dot structure for carbon
monoxide?
(A)
(B)
(C)
(D)
(E)
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12
GO ON TO THE NEXT PAGE.
3. What is the correct IUPAC name for the
compound shown above?
(A)
(B)
(C)
(D)
(E)
trans-3-methyl-3-pentene
cis-2-ethyl-2-butene
(E)-3-methyl-2-pentene
(Z)-3-methyl-2-pentene
(Z)-2-ethyl-2-butene
4. What is the total number of stereoisomers
possible for the compound shown above?
(A) 3
(B) 4
(C) 6
(D) 8
(E) 16
5. The total number of peptide bonds in the structure shown above is
(A)
(B)
(C)
(D)
(E)
1
2
3
4
5
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13
6. A 0.10 L solution of Cl(aq) is titrated with
1.0 – 103 M Ag+(aq). The end point is reached
when 0.025 L of the Ag+ solution has been
added. What was the concentration of Cl in
the original solution?
(A)
(B)
(C)
(D)
(E)
1.0 – 104 M
2.5 – 104 M
4.0 – 104 M
8.0 – 104 M
1.0 – 103 M
C(s) + CO2(g) U 2 CO(g)
7. DH for the reaction shown above is greater than
zero. Assuming DH is independent of temperature, which of the following statements about the
percent yield of CO(g) is true?
9. Assuming that air is approximately 80 percent
nitrogen and 20 percent oxygen by volume, which
of the following is closest to the density of air at
0’C and 1 atmosphere?
(A)
0.01 g/L
(B)
0.1 g/L
(C)
1 g/L
(D) 10 g/L
(E) 100 g/L
10. How many S bonds are there in acetylene, shown
above?
(A)
(B)
(C)
(D)
(E)
(A)
(B)
(C)
(D)
It increases as the amount of C(s) increases.
It increases as the temperature increases.
It decreases as the temperature increases.
It doubles when the initial partial pressure of
CO2 is doubled.
(E) It increases when the total pressure of the
reaction system increases.
[A]
[B]
Initial Rate
0.50 M
0.50 M
0.25 M
1.00 M
0.50 M
1.00 M
0.50 M
1.00 M
10 M s1
20 M s1
5 M s1
40 M s1
8. The initial rates given above were determined
for the reaction A + 2 B  AB2. What is
the overall rate law for this reaction?
1
2
3
4
5
1. CHF2CH2CH2CO2H
2. CH3CF2CH2CO2H
3. CH3CH2CF2CO2H
4. CH3CH2CH2CO2H
11. In which of the following are the carboxylic acids
shown above listed in order of decreasing acidity,
from most acidic to least acidic?
(A)
(B)
(C)
(D)
(E)
1
1
3
3
4
>
>
>
>
>
2
4
2
4
1
>
>
>
>
>
3
3
1
1
2
>
>
>
>
>
4
2
4
2
3
(A) Rate = k[A]2[B]2
(B) Rate = k[A]2[B]
(C) Rate = k[A][B]2
(D) Rate = k[A][B]
(E) Rate = k
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14
GO ON TO THE NEXT PAGE.
12. Which of the following is a 1,4-addition product
of the reaction shown above?
(A)
15. The half-life of 14C is 5,730 years. All of
the following are true for the method of
carbon dating EXCEPT:
(A)
14
C undergoes b-decay to produce 14N.
(B) The 14C content of an organism decreases
after it dies.
(B)
(C) The 14C/12C ratio is the same in living
terrestrial organisms as in the atmosphere.
(C)
(D) The 14C/12C ratio can be used to date a
sample from a dead organism.
(D)
(E) Carbon dating is equally useful for
samples that are millions of years old as for
samples that are about 10,000 years old.
(E)
13. Which of the following is a weak Brønsted-Lowry
acid?
(A)
(B)
(C)
(D)
(E)
HCl
HNO3
H2SO4
H2S
HClO4
14. Which of the following correctly lists the species
in order of increasing radius from smallest to
largest?
(A)
(B)
(C)
(D)
(E)
K+ < Ar < Cl
Ar < Cl < K+
K+ < Cl < Ar
Cl < Ar < K+
Ar < K+ < Cl
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16. The curve shown above illustrates the PV
behavior of a real gas, where V is the molar
volume. According to the van der Waals model
for nonideal gas behavior, the values of PV / RT
greater than 1.0 at high pressures are due to
(A) the effects of increased rate of collision of the
molecules with the walls of the container
(B) the effects of dissociation of individual gas
molecules
(C) the effects of the volume occupied by the
molecules themselves
(D) the effects of forces of attraction between
molecules
(E) ideal gas behavior in this pressure region
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15
O3 ( g ) 
3
O (g)
2 2
17. For the reaction shown above at 298 K,
'G’ = 163 kJ/mol. What is the value of the
equilibrium constant, KP, for this reaction?
(A)
(B)
(C)
(D)
(E)
KP
KP
0.0
KP
KP
>
=
<
=
<
1.0
1.0
KP < 1.0
0.0
0.0
18. In an isolated hydrogen atom, the 2px orbital has
the same principal quantum number, n, as which
of the following orbitals?
I. 2s
II. 2pz
III. 3px
(A)
(B)
(C)
(D)
(E)
(A) Diamond
(B) Graphite
(C) C60
(D) C70
(E) C22
20. Of the following covalent bonds, which has
the greatest bond dissociation energy?
(A)
(B)
(C)
(D)
(E)
C == C
O == O
C == Si
Si œœ Si
C œœ O
I only
II only
III only
I and II only
II and III only
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16
19. Which of the following is NOT an allotrope of
carbon?
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21. Assuming complete dissociation, which of the
following is NOT true about a 1.00 M Mg(NO3)2
solution? (Molar masses: Mg = 24.30 g;
23. Which of the following is the aldol condensation
product of butanal (CH3CH2CH2CHO) ?
(A)
NO3 = 62.01 g; Mg(NO3)2 = 148.31 g)
(A) The concentration of nitrate ions is
2.00 mol L1.
(B) The total concentration of ions is
3.00 mol L1.
(C) The total mass of solute in 1.00 L of this
solution is 148 g.
(D) There are 2.43 g of Mg2+ in 100 mL of
this solution.
(E) There are 6.20 g of NO3 in 100 mL of
this solution.
22. A 499 mg sample of CuSO4ⴢnH2O is heated
to drive off the waters of hydration and then
reweighed to give a final mass of 319 mg. Given
that the sample contains 2.0 mmol of Cu, what
is the average number of waters of hydration, n,
in CuSO4ⴢnH2O ?
(A)
(B)
(C)
(D)
(E)
(B)
(C)
(D)
(E)
2.0
5.0
10.
18
20.
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17
N
H
Naphthalene
Pyrrole
CH
N
Cycloheptatriene
CH 2
Styrene
Pyridine
24. Which of the following statements correctly applies Hückel’s rule to the molecules shown above?
(A)
(B)
(C)
(D)
(E)
Naphthalene is not monocyclic; therefore it cannot be aromatic.
Pyrrole is not a hydrocarbon; therefore it cannot be aromatic.
Cycloheptatriene is not completely conjugated; therefore it cannot be aromatic.
Pyridine is weakly basic; therefore it cannot be aromatic.
Styrene has 8 S electrons; therefore it cannot be aromatic.
25. When 1.0 kJ of heat is added to 5.0 L of an
ideal gas, the gas expands against a constant
external pressure of 1.0 bar to a final volume of
8.0 L. What is the change in internal energy, DU,
for the gas? (1.0 Lⴢbar = 0.10 kJ)
(A)
(B)
(C)
(D)
(E)
0.30 kJ
0.70 kJ
1.0 kJ
1.3 kJ
1.8 kJ
26. Which of the following must be true for adiabatic
processes?
(A)
(B)
(C)
(D)
(E)
CV = CP
DH = 0
DU = 0
DS = 0
q = 0
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18
27. At 37’C, the dissociation constant, Kw , of water
is 2.5 – 1014 (pKw = 13.6). What is the pH of a
1.0 – 105 M NaOH solution at 37’C ?
(A) 4.6
(B) 5.0
(C) 8.6
(D) 9.0
(E) 13.6
__ H+ + __ IO3 + __ I  __ I2 + __ H2O
28. The reaction shown above is not balanced. If the
reaction is balanced using the smallest whole
number coefficients possible, the coefficient for
I will be
(A) 1
(B) 2
(C) 3
(D) 5
(E) 10
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29. Which of the following is the major product of the
reaction shown above?
(A)
30. The reaction of 2-bromobutane with methanol,
as shown above, yields which of the following
as the major product?
(A)
(B)
(C)
(B)
(C)
(D)
(D)
(E)
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(E)
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19
31. Which of the following is the major organic
product of the reaction shown above?
33. Two cylinders, one containing 1 mole of C4H10
gas at 1 atm and the other containing 1 mole
of CH4 gas at 1 atm, are at 288 K. If each gas
absorbs 100 J of heat under conditions of constant
volume, which of the following is true?
(A) The temperature of the CH4 increases more
than the temperature of the C4H10.
(B) The internal energy of both the CH4 and the
C4H10 decreases.
(C) The heat capacity of the C4H10 is less than
the heat capacity of the CH4.
(D) The entropy of both the CH4 and the C4H10
decreases.
(E) The heat transferred to the C4H10 is greater
than the heat transferred to the CH4.
(A)
(B)
(C)
(D)
34. Which of the following statements is true about a
pure substance above its critical point?
(E)
(A)
(B)
(C)
(D)
(E)
One fluid phase is present.
Solid, liquid, and gas are in equilibrium.
Only liquid and gas are in equilibrium.
A liquid forms.
A solid forms.
‡
Ô y1 ( x) y 2 ( x) dx
0
‡
32. In which of the following are the compounds
shown above listed in order of increasing
reactivity to acid-catalyzed dehydration?
(A)
(B)
(C)
(D)
(E)
1
1
2
3
3
<
<
<
<
<
2
3
3
1
2
<
<
<
<
<
3
2
1
2
1
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20
35. If two wavefunctions \1(x) and \2(x)
satisfy the condition given above, the two
wavefunctions are
(A)
(B)
(C)
(D)
(E)
orthogonal
degenerate
normalized
continuous
symmetrical
GO ON TO THE NEXT PAGE.
Aˆ
d2
dx 2
y
sin kx
36. For the equation Ây ay , where Â
and y are shown above, all of the following
are true EXCEPT:
(A) y is an eigenfunction of  .
(B) a is an eigenvalue.
(C) a is an observable.
(D) Â is an operator corresponding to
the observable.
(E) Â is an eigenfunction of a.
37. At standard temperature and pressure, all of
the following compounds exist in the gas state
EXCEPT
(A)
(B)
(C)
(D)
(E)
HCl
HBr
NH3
BH3
LiH
38. The electron configuration of Co in
[Co(NH3)6]Cl3 is
(A)
(B)
(C)
(D)
(E)
[Ar] 4s23d 7
[Ar] 4s23d 4
[Ar] 3d 9
[Ar] 3d 7
[Ar] 3d 6
39. A 0.600 g sample of a pure, weak diprotic acid
gives end points at 20.0 mL and 40.0 mL when
it is titrated with 0.100 M NaOH. What is the
molar mass of the weak acid?
(A)
(B)
(C)
(D)
(E)
120 g
150 g
180 g
300 g
450 g
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40. The figure shown above is a plot of conductance
data obtained during the titration of HCl with
a standard solution of NaOH. Which of the
following statements about the results is NOT
true?
(A) Point B is the end point of the titration.
(B) ·slope AB· > ·slope BC·
(C) The measured conductance increases after
point B because the overall concentration
of ions increases.
(D) Na+ must have a higher equivalent
conductance than H3O+.
(E) Segment BC represents the conductance due
to ions from NaCl and NaOH in solution.
41. The molecular geometry of IF5 is
(A)
(B)
(C)
(D)
(E)
square pyramidal
trigonal planar
bent
linear
octahedral
42. At a given temperature, the vapor pressure of SiF4
is significantly higher than that of SF4 . The major
physical basis for the difference in vapor pressure
is that SiF4 and SF4 have different
(A)
(B)
(C)
(D)
(E)
dipole moments
molar masses
ionization energies
electron affinities
magnetic susceptibilities
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21
43. Which of the protons indicated will be observed
as a doublet in the 1H NMR spectrum of the
molecule shown above?
(A)
(B)
(C)
(D)
(E)
a
b
c
d
e
45. Acyclic conjugated dienes may exist in two
conformations, as shown above. Based on
differences in steric strain, which of the following
dienes has the greatest preference for the s-trans
conformation?
(A)
(B)
(C)
Na
CH3CH2C œœ CCH2CH3 JJJJJJJJJJJJG
liquid NH3
(D)
44. Which of the following is the major product of the
reaction shown above?
(E)
(A) CH3CH2CH2CH2C œœ CNa
(B) CH3CH2CH2CH2CH2CH3
(C) cis-CH3CH2CH == CHCH2CH3
(D) trans-CH3CH2CH == CHCH2CH3
(E)
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22
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48. Based on the molecular orbital model, which of
the following is the number of unpaired electrons
and the bond order for the superoxide ion, O2 ?
46. Which of the following substances is
in equilibrium with cyclopentanone
and HCN shown above?
(A)
(A)
(B)
(C)
(D)
(E)
Unpaired Electrons
1
1
1
2
2
49. For a system at thermal equilibrium, which of
the following is the Boltzmann distribution
expression for the probability, pi , that a single
molecule is in the ith energy state with
energy ei ?
(B)
(C)
(D)
(A) pi
ei / kT
(B) pi
1 e ei / kT
(C) pi
È ‡ e / kT Ø
ei / kT
i
É e
Ù e
Êi 0
Ú
(D) pi
(E)
(E) pi
47. All of the following elements have at least one
isotope that is not radioactive EXCEPT
(A)
(B)
(C)
(D)
(E)
Bond Order
0.5
1.5
2.5
1
2
O
Pb
Sn
No
He
e ei / kT
Ni
e ei / kT
È ‡ e / kT Ø
i
ÉÇe
Ù
Êi 0
Ú
50. Which of the following expressions involving
fugacity, f, is correct as P  0 ?
(A) f
(B) f
(C) f
(D) f
(E) f
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Ç
P
1
P
1
1
V
V
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23
51. Sodium acetate spontaneously crystallizes out
of a supersaturated solution on standing or on the
addition of a seed crystal. Which of the following
is true for the thermodynamic quantities of this
system for this process?
(A)
(B)
(C)
(D)
(E)
DS < 0, DH < 0
DS < 0, DG > 0
DS > 0, DH > 0
DS > 0, DG < 0
DG < 0, DH > 0
52. If ideal gas behavior is assumed, for which of
the following reactions does DH equal DU ?
54. Which of the following is the major product of the
reaction shown above?
(A)
(B)
(A) N2O4(g)  2 NO2(g)
(B) CH4(g) + 2 O2(g)  CO2(g) + 2 H2O(l)
1
(C) SO2(g) +
O (g)  SO3(g)
2 2
(D) Br2(l) + 3 Cl2(g)  2 BrCl 3 (g)
(C)
(E) Cl2(g) + F2(g)  2 ClF(g)
53. PbF2(s), which is slightly soluble in water, is
dissolved in water to form a saturated solution
in equilibrium with solid PbF2 . Which of the
following will cause additional PbF2(s) to
dissolve?
(A)
(B)
(C)
(D)
(E)
Adding HNO3
Adding Pb(NO3)2
Adding a seed crystal
Adding solid PbF2
Evaporating some of the water to decrease
the volume of solution
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24
(D)
(E)
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55. Which of the following is the product of the
reaction shown above?
(A)
(B)
56. Which of the following is the major product of the
reaction shown above?
(A)
(B)
(C)
(C)
(D)
(D)
(E)
(E)
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25
59. The heat of fusion of ice is 333.5 J/g. The entropy
change for the water when freezing 5.0 g of water
at 0qC and 1 atm pressure is
57. Which of the following is the major organic
product of the reaction shown above?
(A)
(A) 6.1 J/K
(B) 1.2 J/K
(C) 0
(D) 1.2 J/K
(E) 6.1 J/K
rate
(B)
60. Many enzyme reactions follow the MichaelisMenten rate law shown above, where V and Km
are constants and [S] is the concentration of
substrate that is undergoing a catalyzed reaction.
When [S] >> Km , what is the apparent order of
the reaction?
(C)
(D)
(A)
(B)
(C)
(D)
(E)
(E)
˜U
˜V
P T
T
˜P
˜T
V
58. Given the expression above, what is the value of
˜U
for an ideal gas undergoing isothermal
˜V T
expansion? (PV = nRT for an ideal gas.)
(A) P V [S]
K m [S]
nR
V
(B) nR
(C) P
(D) 1
Zero order
One-half order
First order
Second order
Third order
61. If for Ni(OH)2 the Ksp is 8.0 – 1018, then the
expression used to calculate the molar solubility S
of Ni(OH)2 is
(A) S
3
2.0 – 10 18
(B) S
3
4.0 – 10 18
(C) S
3
8.0 – 10 18
(D) S
3
5.0 – 10 19
(E) S
3
1.5 – 10 19
(E) 0
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62. Of the following compounds, which reacts
most rapidly with water?
(A)
64. All of the following reactions are examples of the
Lewis definition of acid-base behavior EXCEPT
(A) FeCl3 + Cl  [FeCl4] (B) I2 + I  I3
(B)
(C) SO3 + H2O  H+ + HSO4
(D) Zn(s) + I3  Zn2+ + 3I
(E) NH3 + H2O  NH4+ + OH
(C)
(D)
(E)
65. Of the following, which is the weakest oxidizing
agent?
(A)
(B)
(C)
(D)
(E)
MnO4 aq)
H2O2 aq)
I2(s)
H+(aq)
Mg(s)
63. Which of the following compounds will react
with (CH3)2NH to form an enamine?
(A) CH3CH2CHO
(B) CH3CH2CO2H
(C) CH3CH2CH2OH
(D)
(E)
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27
66. Which of the following reactions proceeds via a carbene
(or carbenoid) intermediate?
(A)
(B)
(C)
(D)
(E)
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28
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67. Which of the following is the major carbocation
rearrangement product of the reaction shown
above?
(A)
(B)
(C)
(D)
(E)
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29
[Benzene], mg/mL
[Ethylbenzene], mg/mL
Benzene peak area, mVⴢs
Ethylbenzene peak area, mVⴢs
Standard
Sample
50
10
2,500
1,000
10
2,500
500
68. The table above shows chromatographic data for the analysis
of benzene using an ethylbenzene internal standard. What is
the benzene concentration of the sample in mg/mL ?
(A)
(B)
(C)
(D)
(E)
10
25
80
100
250
DE
69. A high-resolution infrared absorption spectrum
of a heteronuclear diatomic molecule is shown
above. Information about which of the following
kinds of energy levels of the diatomic molecule
can be obtained from this spectrum?
I. Electronic
II. Vibrational
III. Rotational
(A)
(B)
(C)
(D)
(E)
I only
II only
III only
II and III only
I, II, and III
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30
È 1
1 Ø
h c RH É 2 2 Ù
Ê n1
n2 Ú
70. The ionization energy of a ground state H atom
is 13.6 eV. Given the equation shown above,
how much energy is needed to excite an electron
in an H atom from a state with quantum number
n = 1 to a state with n = 2 ?
(A)
(B)
(C)
(D)
(E)
(1/8) 13.6 eV
(1/4) 13.6 eV
(1/2) 13.6 eV
(3/4) 13.6 eV
13.6 eV
71. All of the following are true about lasers
EXCEPT:
(A)
(B)
(C)
(D)
The light does not diverge significantly.
The light is emitted only in pulses.
The light waves are in phase.
The light is essentially all the same
wavelength.
(E) The light is essentially all the same
frequency.
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75. In a particular TLC separation, the stationary
phase is a C2 plate (= ¶CH2CH3), and the mobile
phase is 60% methanol:40% water (v:v). Of the
following compounds, which will likely travel the
greatest distance during the analysis?
(A)
(B)
72. Consider the ground electronic state S0, the
excited singlet state S1, and the triplet state T1
of a molecule, shown above. The S1  S0
transition corresponds to
(A)
(B)
(C)
(D)
(E)
a forbidden transition
fluorescence
phosphorescence
photoionization
vibrational relaxation
73. Graphite reacts with potassium to produce a
compound with the empirical formula KC8 . Of
the following, which is the best description of this
compound’s structure?
(C)
(D)
(A) K+ ions close-packed with polyhedral
C8 ions
(B) K ions close-packed with polyhedral
C8+ ions
(E)
(C) K+ ions packed with C22 ions
(D) Negatively charged hexagonal carbon layers
with intercalated K+ ions between them
(E) An expanded diamond lattice with K+ ions
in the tetrahedral holes
74. The experimental technique most suited for the
determination of the three-dimensional structure
of a crystalline solid is
(A)
(B)
(C)
(D)
(E)
UV-visible spectroscopy
X-ray diffraction
measurement of colligative properties
polarimetry
Fourier transform mass spectrometry
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31
76. Which of the following statements about sulfur
dioxide is true?
(A) It forms an SS bonded dimer in condensed
phases.
(B) It is the anhydride of sulfuric acid, H2SO4.
(C) It plays an important physiological role in
the transmission of nerve impulses.
(D) Its OSO angle is 180’.
(E) It is a product of the combustion of
fossil fuels that contain sulfur.
78. In their metallic form, elements from which
of the following groups are usually effective
hydrogenation catalysts?
(A)
(B)
(C)
(D)
(E)
Alkaline earth metals
Platinum metals
Halogens
Actinides
Group 12 metals
77. Which of the following statements about polonium,
the heaviest Group 16 element, is NOT true?
(A) Polonium is the least metallic of the Group
16 elements.
(B) Polonium has the lowest ionization energy
of the Group 16 elements.
(C) Polonium atoms are the largest of the Group
16 elements.
(D) Polonium is expected to be a solid at room
temperature and pressure.
(E) When
forms
209
Po undergoes alpha decay, it
205
79. Which of the following is the product of the
reaction shown above?
(A)
(B)
(C)
Pb .
(D)
(E)
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32
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80. Which of the following is the product of the series of reactions shown above?
(A)
(B)
(C)
(D)
(E)
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33
81. Which of the following is a step in the mechanism of the hydrolysis of the ester shown above?
(A)
(B)
(C)
(D)
(E)
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34
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82. Which of the following is the major product of the reaction
shown above?
(A)
(B)
(C)
(D)
(E)
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35
A  Products
83. For the reaction shown above, the experimental
rate law is rate = k[A]2. Which of the following
is the integrated rate law for this reaction?
(A)
[A]0
[A]
(B) ln
[A]0
[A]
kt
k1
JJJJJG
J B
A HJJJJJ
k 1
K1
k2 G
HJJJJJ
J C
A JJJJJJ
k 2
K2
>[email protected]
>[email protected]
>[email protected]
>[email protected]
1
2
k1 = 10 k2
at t = 0: [B] = [C] = 0
kt
(C) [A] [A]0
85. Given the information above, the concentrations
of B and C and the control (thermodynamic or
kinetic) of the system at short and long times are
described by which of the following?
kt
(D) [A]2 [A]20
1
1
(E)
[A] [A]0
kt
Short Time
Long Time
(A)
[B] > [C]
kinetic
[C] > [B]
thermodynamic
(B)
[C] > [B]
kinetic
[B] > [C]
thermodynamic
(C)
[B] > [C]
thermodynamic
[C] > [B]
kinetic
(D)
[C] > [B]
thermodynamic
[B] > [C]
kinetic
(E)
[B] > [C]
kinetic
[B] > [C]
kinetic
kt
k1
ZZZZ
X
NO + NO YZZZ
Z N2O2
k1
N2O2 + O2
k2
 2 NO2
84. Consider the mechanism shown above for
oxidation of NO by O2. Based on the steady
state approximation, which of the following
conditions is true for this mechanism?
d[NO2 ]
d[N 2 O2 ]
2
dt
dt
d[NO2 ]
0
(B)
dt
d[N 2 O2 ]
(C)
0
dt
(D) [N2O2] = 0
(A)
86. In CrF2(s), the coordination of the six F’s
around the Cr is a distorted octahedron with
four short and two long C r F bonds. Which
of the following best explains this observation?
(A)
(B)
(C)
(D)
(E)
F has a 1 anionic charge.
Cr2+ has a low cationic charge.
The Jahn-Teller effect
Spin-orbit coupling in Cr2+
The formation of C r Cr bonds in CrF2(s)
(E) k = k1 + k1
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87. Each of the following molecules can act as
a chelating ligand EXCEPT
(A)
(B)
(C)
(D)
(E)
H2NCH2CH2NH2
CH3NHCH2CH2NH2
HC(CH2CH2NH2)3
CH3NHCH2CH2CH3
N(CH2CH2NH2)3
88. Which of the following is NOT a desirable
property of an indicator to be used in a
complexometric titration that involves EDTA?
(A) The indicator should be a Lewis base.
(B) The indicator should bind more tightly
to the analyte metal than does EDTA.
(C) The complexation reaction between the
indicator and the analyte metal should
be reversible.
(D) The uncomplexed form of the indicator
should be a different color than the
indicator-metal complex.
(E) The indicator should be highly soluble
in the sample.
89. Which of the following statements about
complexes that form between metals, Mn+, and
EDTA in aqueous solutions is true?
(A) Metal-EDTA complexes have an equilibrium
concentration that is independent of pH.
(B) Metal-EDTA complexes are usually highly
colored.
(C) Metal-EDTA complexes are often 2:1 in
stoichiometry.
(D) Metal-EDTA complexes are less stable than
the corresponding metal-ammine
complexes.
(E) The presence of other complexing ligands
in solution affects the equilibrium concentrations of metal-EDTA complexes.
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90. Which of the following compounds exists in
stereoisomeric forms?
(A) [Pt(NH3)4 ]2+
(B) [Pt(NH3)3Cl]+
(C) [Pt(NH3)2Cl2]
(D) [Pt(NH3)Cl3] (E) [PtCl4 ]2
91. All of the following are recognized as pathways
that can reduce the CO2 level in the atmosphere
EXCEPT
(A)
(B)
(C)
(D)
(E)
dissolution in the oceans
photosynthesis
respiration
reduced burning of fossil fuels
rainfall with dissolved CO2
92. Which of the following is a wavefunction,
y (r , q , f ) , for an s electron?
(A) N 2 Zr
e
a
Zr
2a
(B) N re
Zr
2a
cos q
(C) N re
Zr
2a
sin q cos f
Zr
N re 2 a
sin q sin f
(D)
(E) N r 2 e
Zr
3a
3cos2 q 1
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37
93. Due to electron-electron interactions, it is not
possible to obtain exact solutions to the
Schrödinger equation for many-electron atoms.
One approach that addresses this difficulty uses
(A)
(B)
(C)
(D)
(E)
the rigid-rotor approximation
the harmonic oscillator approximation
the principle of corresponding states
effective nuclear charges
the Franck-Condon principle
94. Of the following linear combinations of atomic
orbitals centered on two atoms, A and B, which
best represents the ground-state molecular orbital
for the hydrogen molecule, H2 ?
(A)
(B)
(C)
(D)
(E)
y
y
y
y
y
=
=
=
=
=
N (1sA
N (1sA
N (1sA
N (1sA
N (2pA
+
+
+
1sB)
1sB)
2pB)
2pB)
2pB)
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95. Acetic acid is extracted from ether into water.
Which of the following actions will NOT
increase the fraction of acetic acid removed
from ether?
(A)
(B)
(C)
(D)
(E)
Raising the pH of the water
Increasing the volume of water
Decreasing the volume of ether
Adding benzoic acid to the water
Adding ammonia to the water
96. The ionic strength of an aqueous 0.10 M Pb(NO3)2
solution is
(A)
(B)
(C)
(D)
(E)
0.10 M
0.25 M
0.30 M
0.50 M
0.60 M
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97. Which two of the following are the propagation steps in the allylic bromination of cyclohexene shown above?
I.
II.
III.
IV.
V.
(A)
(B)
(C)
(D)
(E)
I and II
I and IV
I and V
II and V
III and IV
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39
101. Which of the following is a strong acid in pure
liquid HF?
(A) H2O
98. The transformation shown above is carried out by
which of the following reagents?
(A)
(B)
(C)
(D)
(E)
KOH
BH3/THF then H2O2, NaOH
Hg(O2CCH3)2/H2O then NaBH4
H2O, H2SO4
H2O, peroxides
(B) SbF5
(C) CH3COOH
(D) NH3
(E) NaF
102. What is the most common natural form in which
fluorine is found on Earth?
(A)
(B)
(C)
(D)
(E)
99. Which of the following could carry out the
conversion shown above?
(A) 1. Mg, ether
2. CO2
3. H3O+
(B) 1. O3
2. Zn, H2O
(C) 1. KMnO4, OH
2. H3O+
(D) 1. NaOH
2. CrO3, H2SO4
(E) 1. Li
2. H2C == O
3. H3O+
100. Vitamin B12 , an essential nutrient for humans,
contains which of the following elements?
(A)
(B)
(C)
(D)
(E)
Cobalt
Chromium
Copper
Zinc
Iron
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40
As a fluoride ion in various minerals
As XeF2(s)
As the weak acid HF(aq)
As the free element F2(g)
In various fluorocarbon compounds in the
atmosphere
En = n2h2/8mL2
103. For a particle of mass m in a one-dimensional
box of length L, the energy of the particle is given
by the equation shown above. How much energy
is required to promote the particle from the state
with quantum number n = 2 to the state with
quantum number n = 3 ?
(A) 9h2/8mL2
(B) 5h2/8mL2
(C) 4h2/8mL2
(D) h2/8mL2
(E) 0
104. A large activation energy implies which of the
following about a reaction?
(A)
(B)
(C)
(D)
(E)
It is spontaneous.
It is highly endothermic.
It is at equilibrium.
It is very rapid.
It has a highly temperature-dependent
rate constant.
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105. Analysis of a bottle of 100 mg vitamin C tablets
yields an average vitamin C content of 99.8 mg,
with a standard deviation of ±0.3 mg. Assuming
Gaussian statistics, which of the following is true?
(A) None of the tablets contains less than 99.5
mg of vitamin C.
(B) 68% of the tablets contain between 99.5 and
100.1 mg of vitamin C.
(C) 97% of the tablets contain between 99.5 and
100.1 mg of vitamin C.
(D) All of the tablets contain less than 100 mg of
vitamin C.
(E) The average value is incorrect.
108. Which of the following is the major organic
product of the reaction sequence shown above?
(A)
106. In an experiment to test the de Broglie hypothesis,
a beam of high-energy electrons with momenta
p = meu = 6 – 1024 kgⴢm/s
(B)
would be scattered by a nickel crystal with a
pattern similar to that of which of the following?
(A) X-rays of wavelength O = h/p
(B) Electromagnetic radiation with wavelength
O = p/h
(C) A beam of protons with velocity u
(D) Billiard balls undergoing perfectly elastic
collisions
(E) Visible light with a mixture of frequencies
frequently characterized as “white”
107. Which of the following is true about the quantum
yield for photodecomposition of a chromophore?
(A) It depends on the intensity of the light source
used for the photolysis.
(B) It depends on the duration of the light source
used for the photolysis.
(C) It is the reciprocal of the fluorescence
lifetime.
(D) It has a value of either 0 or 1, reflecting the
quantum nature of photons.
(E) It is the ratio of the number of chromophores
decomposed to the number of photons
absorbed.
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(C)
(D)
(E)
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41
109. Which of the following is the major organic product of the
sequence of reactions shown above?
(A)
(B)
(C)
(D)
(E)
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42
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110. A characteristic common to polymers that can be
made to conduct electricity, such as polyacetylene
and polypyrrole, is
(A) the presence of stereogenic centers of
the same configuration
(B) a monodisperse distribution in molecular
weight
(C) a very low glass transition temperature
(D) conjugation throughout the polymer chain
(E) a high degree of cross-linking
111. Which of the following complexes does NOT
contain a significant S component in the
metal-ligand bonding?
(A) [Co(NH3)6]3+
(B) [Fe(CO)5]
(C) [CrO4]2
(D) [Co(CN)6]3
(E) [Cr(K-C6H6)2]
112. In an experiment to determine riboflavin by
fluorescence spectrometry, a series of riboflavin
standards was analyzed and gave a calibration
line with a slope of 1000 ppm and a y-intercept
of 25. If a sample gave a fluorescence reading of
750, the riboflavin concentration (in ppm) of the
sample is
(A)
(B)
(C)
(D)
(E)
0.0750
0.0775
0.725
0.775
7.50
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113. The rate constant for a first-order reaction
R  P is 0.010 s. The concentration of R
decreases to one-half of its initial value after
(A)
2
s
0.010
(B)
ln 2
s
0.010
(C)
1
s
2(0.010)
(D)
1
s
4(0.010)
(E) 5(0.010) s
114. The activated-complex theory (or transition
state theory) assumes that an equilibrium exists
between the
(A)
(B)
(C)
(D)
(E)
activated complex and reactants only
activated complex and products only
products and reactants only
reactants, activated complex, and products
system (reaction) and surroundings
115. Oxidation of (R)-3-bromo-5-hydroxypentanoic
acid, shown above, yields the corresponding
3-bromopentanedicarboxylic acid product that is
(A) a mixture of two diastereomers in
unequal amounts
(B) a racemic mixture
(C) a single pure enantiomer
(D) a meso compound
(E) an achiral compound
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43
116. Of the following molecules, which most readily
undergoes a unimolecular elimination (E1)
reaction?
(A)
118. AgCl is insoluble in water at room temperature.
The dissolution of AgCl(s) into aqueous
ammonia can best be explained as the
(A)
(B)
(C)
(D)
(E)
(B)
coprecipitation of NH4Cl(s)
formation of AgNO3
oxidation of Ag+ in aqueous base
reduction of Ag+ by NH3
formation of the complex cation Ag(NH3)2+
(C)
d[HBr]
dt
(D)
(E)
117. Compounds have been prepared from which of
the following noble gas elements?
(A)
(B)
(C)
(D)
(E)
He only
He and Ne only
Ne and Ar only
He, Ne, and Ar
Kr, Xe, and Rn
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44
1
k[H 2 ][Br2 ] 2
119. The rate law shown above is for the reaction
H2 + Br2  2 HBr at the early stages of the
reaction, when [HBr] is low and holds over
a wide range of concentrations of H2 and Br2.
An explanation that is consistent with the halfinteger order in Br2 is given by which of the
following?
(A) The mechanism is an elementary reaction
involving one Br2 and two H2 molecules.
(B) The overall reaction is not accomplished by
a single elementary step.
(C) The rate-limiting step involves one Br2 and
two H2 molecules.
(D) The rate-limiting step involves one H2 and
two Br2 molecules.
(E) Quantum mechanical tunneling affects
the rate.
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120. In a mixture of He and Ar atoms in thermal
equilibrium, what is the average speed of the He
atoms, uHe, compared with the average speed of
the Ar atoms, uAr ? (mHe is the mass of He
atoms, and mAr is the mass of Ar atoms.)
(A) uHe
uAr
(B)
uHe
uAr
mHe
mAr
(C)
uHe
uAr
mAr
mHe
u
(D) He
uAr
mHe
mAr
uHe
uAr
mAr
mHe
(E)
121. Which of the following is the major nucleophilic
substitution product of the reaction shown above?
(A)
(B)
(C)
(D)
(E)
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45
122. What is the major organic product from the sequence of reactions shown above?
(A)
(B)
(C)
(D)
(E)
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46
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125. For the species H2 , HD, HT, and D2 , all
of the bond strengths (and force constants) are
the same. Which of the following will have the
lowest fundamental vibration frequency?
(D = deuterium; T = tritium)
123. A simple electronic band structure for lithium
metal is shown above. Based on this band
structure, which of the following is correct?
(A) Electrons occupy one of two distinct energy
states in the 2s band.
(B) If the number of lithium atoms in a piece of
lithium metal is represented by N, then the
number of 2s orbitals that make up the 2s
band is 2N.
(C) The electrons in the 2s band are each
localized on a particular lithium atom.
(D) Electrons must be promoted to the 2p band
in order to conduct.
(E) The partial filling of the 2s band is responsible for the metallic character of lithium.
(A)
(B)
(C)
(D)
(E)
H2
HD
HT
D2
All will have the same fundamental vibration
frequency.
126. Which of the following is NOT true about Raman
scattering?
(A) Raman scattering requires a change in dipole
moment.
(B) Raman frequency shifts are independent of
the frequency of excitation.
(C) Raman scattering results in equal shifts in
frequency above and below the incident
frequency.
(D) Some Raman-active transitions are not
infrared active.
(E) Raman scattering requires a change in
polarizability.
H3C O C(CH3)3
124. Methyl t-butyl ether (MTBE), shown above, is a
controversial gasoline additive. Of the following
analytical techniques, which would be the best
method to measure quantitatively trace amounts
of MTBE in contaminated groundwater?
(A)
(B)
(C)
(D)
(E)
Capillary electrophoresis
Gas chromatography
Atomic absorption spectroscopy
Fluorescence spectroscopy
EPR spectroscopy
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47
127. Which of the following is formed when a solution of E-D-glucopyranose is allowed to stand in methanol that
contains a small amount of an acid catalyst, as indicated in the equation shown above?
(A)
(B)
(C)
(D)
(E)
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48
GO ON TO THE NEXT PAGE.
pKa1
pKa2
pKa3
128. The species shown above is
(A)
(B)
(C)
(D)
(E)
a nucleotide
a peptide
a diterpene
a disaccharide
an alkaloid
129. Which of the following is NOT a known,
relatively stable compound of uranium?
(A)
(B)
(C)
(D)
(E)
2.15
7.20
12.15
130. The pKa1 , pKa2 , and pKa3 values for H3PO4
are given above. When 50.0 mL of
0.10 M Na2HPO4 are mixed with 50.0 mL of
0.10 M Na3PO4, the pH of the resulting solution
will be closest to
(A) 2.15
(B) 4.68
(C) 7.20
(D) 9.68
(E) 12.15
UF6
UO2
UO3
U(CH3)2
U(C8H8)2
If you finish before time is called, you may check your work on this test.
Unauthorized copying or reuse of
any part of this page is illegal.
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49
NO TEST MATERIAL ON THIS PAGE
50
NO TEST MATERIAL ON THIS PAGE
51
NOTE: To ensure prompt processing of test results, it is important that you fill in the blanks exactly as directed.
I
SUBJECT TEST
A. Print and sign
your full name
in this box:
PRINT: ___________________________________________________________________
(LAST)
(FIRST)
(MIDDLE)
SIGN: ____________________________________________________________________
6. TITLE CODE
Copy this code in box 6 on
your answer sheet. Then
fill in the corresponding
ovals exactly as shown.
2 7 01 4
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0
0
0
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1
1
1
1
1
2
2
2
2
2
3
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3
3
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4
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5
5
5
5
6
6
6
6
6
7
7
7
7
7
8
8
8
8
8
9
9
9
9
9
Copy the Test Name and Form Code in box 7 on your answer
sheet.
Chemistry
TEST NAME ___________________________________
GR0627
FORM CODE ____________________________________
GRADUATE RECORD EXAMINATIONS SUBJECT TEST
B. The Subject Tests are intended to measure your achievement in a specialized field of study. Most of the questions are
concerned with subject matter that is probably familiar to you, but some of the questions may refer to areas that you
have not studied.
Your score will be determined by subtracting one-fourth the number of incorrect answers from the number of correct
answers. Questions for which you mark no answer or more than one answer are not counted in scoring. If you have
some knowledge of a question and are able to rule out one or more of the answer choices as incorrect, your chances of
selecting the correct answer are improved, and answering such questions will likely improve your score. It is unlikely
that pure guessing will raise your score; it may lower your score.
You are advised to use your time effectively and to work as rapidly as you can without losing accuracy. Do not spend
too much time on questions that are too difficult for you. Go on to the other questions and come back to the difficult
ones later if you can.
YOU MUST INDICATE ALL YOUR ANSWERS ON THE SEPARATE ANSWER SHEET. No credit will be given
for anything written in this examination book, but you may write in the book as much as you wish to work out your
answers. After you have decided on your response to a question, fill in the corresponding oval on the answer sheet.
BE SURE THAT EACH MARK IS DARK AND COMPLETELY FILLS THE OVAL. Mark only one answer to each
question. No credit will be given for multiple answers. Erase all stray marks. If you change an answer, be sure that all
previous marks are erased completely. Incomplete erasures may be read as intended answers. Do not be concerned that
the answer sheet provides spaces for more answers than there are questions in the test.
Example:
Sample Answer
What city is the capital of France?
(A)
(B)
(C)
(D)
(E)
Rome
Paris
London
Cairo
Oslo
A
B
C
D
E
A
B
C
D
E
A
B
C
D
E
A
B
C
D
E
A
B
C
D
E
CORRECT ANSWER
PROPERLY MARKED
IMPROPER MARKS
DO NOT OPEN YOUR TEST BOOK UNTIL YOU ARE TOLD TO DO SO.
®
52
Educational Testing Service
Princeton, New Jersey 08541
Scoring Your Subject Test
The Chemistry Test scores are reported on a 200 to 990
score scale in ten-point increments. The actual range
of scores is smaller, and it varies from edition to edition
because different editions are not of precisely the same
difficulty. However, this variation in score range is
usually small and should be taken into account mainly
when comparing two very high scores. In general,
differences between scores at the 99th percentile
should be ignored. The score conversion table on
page 55 shows the score range for this edition of the
test only.
The worksheet on page 54 lists the correct answers
to the questions. Columns are provided for you to
mark whether you chose the correct (C) answer or
an incorrect (I) answer to each question. Draw a line
across any question you omitted, because it is not
counted in the scoring. At the bottom of the page,
enter the total number correct and the total number
incorrect. Divide the total incorrect by 4 and subtract
the resulting number from the total correct. Then
round the result to the nearest whole number. This
will give you your raw total score. Use the total score
conversion table to find the scaled total score that
corresponds to your raw total score.
Example: Suppose you chose the correct answers
to 80 questions and incorrect answers to 46. Dividing
46 by 4 yields 11.5. Subtracting 11.5 from 80 equals
68.5, which is rounded to 69. The raw score of 69
corresponds to a scaled score of 690.
CHEMISTRY TEST
PRACTICE BOOK
53
Worksheet for the Chemistry Test, Form GR0627
Answer Key and Percentages* of Examinees Answering Each Question Correctly
QUESTION
RESPONSE
P+
C
I
QUESTION
RESPONSE
P+
I
QUESTION
RESPONSE
P+
Number
Answer
Number
Answer
Number
Answer
1
2
3
4
5
A
C
C
D
C
83
83
64
63
90
46
47
48
49
50
C
D
B
E
A
89
69
57
50
15
91
92
93
94
95
C
A
D
A
D
89
32
23
75
62
6
7
8
9
10
B
B
D
C
B
91
47
72
48
92
51
52
53
54
55
A
E
A
D
B
44
69
72
27
69
96
97
98
99
100
C
E
B
A
A
68
67
66
73
30
11
12
13
14
15
C
C
D
A
E
85
59
87
70
50
56
57
58
59
60
B
C
E
E
A
51
64
39
50
76
101
102
103
104
105
B
A
B
E
B
27
72
87
65
58
16
17
18
19
20
C
A
D
E
E
42
71
86
78
50
61
62
63
64
65
A
C
A
D
E
34
58
32
48
53
106
107
108
109
110
A
E
C
E
D
47
51
27
48
77
21
22
23
24
25
E
B
E
C
B
82
60
45
68
48
66
67
68
69
70
A
A
D
D
D
45
74
51
59
79
111
112
113
114
115
A
C
B
A
E
51
76
69
29
36
26
27
28
29
30
E
C
D
A
B
71
60
23
67
85
71
72
73
74
75
B
B
D
B
A
65
76
37
97
75
116
117
118
119
120
C
E
E
B
E
78
78
55
51
63
31
32
33
34
35
C
D
A
A
A
60
86
62
50
73
76
77
78
79
80
E
A
B
C
C
62
77
80
62
38
121
122
123
124
125
B
C
E
B
D
79
31
36
66
47
36
37
38
39
40
E
E
E
D
D
66
61
53
55
60
81
82
83
84
85
A
C
E
C
A
78
56
62
60
63
126
127
128
129
130
A
E
C
D
E
40
43
66
27
42
41
42
43
44
45
A
A
B
D
C
82
52
83
40
62
86
87
88
89
90
C
D
B
E
C
72
68
53
54
71
C
C
I
Total Correct (C)
Total Incorrect (I)
Total Score:
C – I/4 = ____________
Scaled Score (SS) = ____________
* The P+ column indicates the percent of CHEMISTRY Test examinees who answered each question correctly; it is based on a
sample of November 2006 examinees selected to represent all CHEMISTRY Test examinees tested between July 1, 2005, and
June 30, 2008.
54
CHEMISTRY TEST
PRACTICE BOOK
Score Conversions and Percents Below*
for GRE Chemistry Test, Form GR0627
TOTAL SCORE
Raw Score
Scaled Score
%
Raw Score
Scaled Score
%
130
128-129
126-127
125
123-124
121-122
119-120
117-118
970
960
950
940
930
920
910
900
99
99
99
99
99
98
97
96
114-116
112-113
110-111
108-109
105-107
103-104
101-102
98-100
96-97
94-95
890
880
870
860
850
840
830
820
810
800
95
94
92
90
88
86
85
82
80
78
68-69
65-67
63-64
61-62
58-60
56-57
54-55
51-53
49-50
47-48
690
680
670
660
650
640
630
620
610
600
49
46
43
40
36
33
31
28
25
23
91-93
89-90
87-88
84-86
82-83
80-81
77-79
75-76
73-74
70-72
790
780
770
760
750
740
730
720
710
700
75
73
71
68
65
63
60
57
55
52
44-46
42-43
40-41
37-39
35-36
32-34
30-31
28-29
25-27
23-24
590
580
570
560
550
540
530
520
510
500
20
17
15
13
11
9
7
6
4
3
21-22
18-20
16-17
14-15
11-13
9-10
6-8
4-5
2-3
0-1
490
480
470
460
450
440
430
420
410
400
2
2
1
1
1
1
1
1
1
1
*Percent scoring below the scaled score is based on the performance of
8,549 examinees who took the CHEMISTRY Test between July 1, 2005, and
June 30, 2008. This percent-below information was used for score reports
during the 2009-10 testing year.
CHEMISTRY TEST
PRACTICE BOOK
55
Evaluating Your Performance
Now that you have scored your test, you may wish to
compare your performance with the performance of
others who took this test. Both the worksheet on page
54 and the table on page 55 use performance data from
GRE Chemistry Test examinees.
The data in the worksheet on page 54 are based
on the performance of a sample of the examinees
who took this test in November 2006. This sample
was selected to represent the total population of GRE
Chemistry Test examinees tested between July 2005
and June 2008. The numbers in the column labeled
“P+” on the worksheet indicate the percentages of
examinees in this sample who answered each question
correctly. You may use these numbers as a guide for
evaluating your performance on each test question.
The table on page 55 contains, for each scaled
score, the percentage of examinees tested between
July 2005 and June 2008 who received lower scores.
Interpretive data based on the scores earned by
examinees tested in this three-year period will be used
by admissions officers in the 2009-10 testing year.
These percentages appear in the score conversion
table in a column to the right of the scaled scores. For
56
example, in the percentage column opposite the scaled
score of 690 is the number 49. This means that 49
percent of the GRE Chemistry Test examinees tested
between July 2005 and June 2008 scored lower than
690. To compare yourself with this population, look at
the percentage next to the scaled score you earned on
the practice test.
It is important to realize that the conditions
under which you tested yourself were not exactly
the same as those you will encounter at a test center.
It is impossible to predict how different test-taking
conditions will affect test performance, and this is only
one factor that may account for differences between
your practice test scores and your actual test scores.
By comparing your performance on this practice test
with the performance of other GRE Chemistry Test
examinees, however, you will be able to determine
your strengths and weaknesses and can then plan a
program of study to prepare yourself for taking the
GRE Chemistry Test under standard conditions.
CHEMISTRY TEST
PRACTICE BOOK
57
q
o
Omit spaces, apostrophes, Jr., II., etc.
E
F
G
H
I
J
K
L
M
N
E
F
G
H
I
J
K
L
M
N
Y
Z
Y
Z
Z
–
–
Y
X
W
V
U
T
S
R
Z
Y
X
W
T
S
Q
P
O
N
M
L
K
J
I
H
G
F
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SIGNATURE:
Country
CENTER:
(Print)
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Z
Z
Room Number
State or Province
Zip or Postal Code
Y
Y
Country
X
X
State or Province
City
M.I.
V
W
V
W
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City
Center Number
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First Name (Given)
–
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P.O. Box or Street Address
Last Name (Family or Surname)
–
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A
MAILING ADDRESS:
(Print)
2.
YOUR NAME:
X
X
V
V
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D
P
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O
B
B
O
A
A
Last Name only (Family Name or Surname) - First 15 Letters
First
Name Middle
Initial Initial
Enter your last name, first name initial (given name), and
1. NAME middle initial if you have one.
E
E
E
7
8
Oct.
Nov.
®
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5. REGISTRATION
NUMBER
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Q3117-06,07/1
9
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1
0
.
BE SURE EACH MARK IS DARK AND COMPLETELY FILLS THE INTENDED SPACE AS ILLUSTRATED HERE:
- SUBJECT TEST
9
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SIDE 1
1
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2
1
0
742862
SHADED AREA FOR ETS USE ONLY
(number in upper right corner of front cover of
your test book)
8. TEST BOOK SERIAL NUMBER
your test book)
FORM CODE (on back cover of
your test book)
7. TEST NAME (on back cover of
MH/wan07190
9
8
7
6
5
4
3
2
1
0
(on back cover of
your test book)
6. TITLE CODE
00101-02954 • TF77E70
9
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7
6
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1
0
(from your admission ticket)
Copyright ® 2007 by Educational Testing Service, Princeton, NJ 08541
All rights reserved. Printed in U.S.A.
9
6
Dec.
5
3
Sept.
3
June
2
1
Aug.
2
May
4
1
April
July
0
Mar.
Feb.
0
Day
Jan.
Year
(U.S.A. only)
Month
4. SOCIAL SECURITY
NUMBER
YOU MAY FIND MORE RESPONSE SPACES THAN YOU NEED. IF SO, PLEASE LEAVE THEM BLANK.
3. DATE OF BIRTH
0
E
GRADUATE RECORD EXAMINATIONS ® E
DO NOT USE INK
E
D
C
B
A
E
D
C
B
A
E
Use only a pencil with soft, black lead (No. 2 or HB) to complete this answer sheet.
Be sure to fill in completely the space that corresponds to your answer choice.
Completely erase any errors or stray marks.
E
D
C
B
A
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77
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39
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79
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3
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A
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A
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82
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45
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E
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7
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9
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86
87
88
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48
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50
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E
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10
11
12
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A
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89
90
91
E
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51
52
53
E
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E
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A
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E
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16
17
18
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E
A
19
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13
14
15
D
C
B
A
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B
A
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B
A
92
93
94
E
D
C
B
E
D
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B
A
E
D
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B
D
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A
C
A
E
A
95
96
E
D
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A
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57
58
D
54
55
56
E
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97
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A
B
A
E
59
B
A
22
23
C
B
A
20
21
D
A
24
C
A
25
E
E
A
E
D
C
E
A
B
E
D
C
B
A
60
61
E
D
B
A
D
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98
D
C
B
B
A
C
D
C
B
A
D
C
E
E
A
62
63
D
B
A
26
27
28
C
D
C
B
A
D
C
E
A
B
D
C
E
A
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99
100
101
B
D
C
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D
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29
C
E
D
C
B
D
A
30
C
E
A
B
E
A
B
D
C
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102
D
C
64
D
B
C
E
A
B
E
A
D
C
65
D
C
B
E
A
B
E
103
B
D
C
B
A
D
C
E
D
C
E
66
B
E
A
B
D
C
E
104
B
D
C
E
D
C
B
A
D
C
B
D
A
C
E
A
B
E
A
B
D
C
E
A
D
C
A
67
68
69
E
A
B
A
C
B
A
31
32
D
B
A
33
34
C
A
35
E
70
B
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105
106
107
B
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A
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C
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108
B
D
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B
A
D
C
E
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A
36
C
E
A
B
E
A
B
D
C
E
109
B
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C
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71
B
E
D
C
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A
B
D
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B
A
72
73
E
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B
A
E
A
B
D
C
E
D
B
A
C
E
D
C
B
D
C
B
E
110
B
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D
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A
B
D
C
B
A
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A
B
A
111
112
113
E
114
E
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74
75
B
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A
76
E
D
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A
37
38
Item responses continued on reverse side.
SIDE 2
CERTIFICATION STATEMENT
Please write the following statement below, DO NOT PRINT.
“I certify that I am the person whose name appears on this answer sheet. I also
agree not to disclose the contents of the test I am taking today to anyone.”
Sign and date where indicated.
SUBJECT TEST
COMPLETE THE
CERTIFICATION STATEMENT,
THEN TURN ANSWER SHEET
OVER TO SIDE 1.
SIGNATURE:
DATE:
TR
C
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A
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C
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200
201
202
203
204
205
206
207
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209
210
A
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C
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147
A
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C
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B
C
D
E
A
B
C
D
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A
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C
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A
B
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A
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148
149
150
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119
120
121
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A
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C
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A
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A
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151
152
153
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122
123
124
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154
155
156
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125
126
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157
158
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127
A
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159
A
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128
129
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A
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C
D
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160
161
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D
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130
A
B
C
D
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162
A
B
C
D
131
132
A
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C
D
E
A
B
C
A
B
C
D
E
163
164
A
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133
134
135
A
B
C
D
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A
A
B
C
D
E
A
B
C
D
E
165
166
167
136
137
138
139
140
141
142
143
144
145
146
A
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C
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A
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A
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168
169
170
171
172
173
174
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176
177
178
TW
TFS
TCS
211
212
213
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214
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216
217
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218
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221
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224
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226
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227
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229
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230
231
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A
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232
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234
235
236
237
238
239
240
241
242
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1R
1W
1FS
1CS
2R
2W
2FS
2CS
3R
3W
3FS
3CS
4R
4W
4FS
4CS
5R
5W
5FS
5CS
6R
6W
6FS
6CS
B. sign your full name here:
B
A
B
A
IF YOU DO NOT WANT THIS ANSWER SHEET TO BE SCORED
A
A
116
117
118
FOR ETS USE ONLY
58
179
180
115
Year
A. Fill in both ovals here . . .
.
YOU MAY FIND MORE RESPONSE SPACES THAN YOU NEED. IF SO, PLEASE LEAVE THEM BLANK.
Day
To cancel your scores from this test administration, you must:
BE SURE EACH MARK IS DARK AND COMPLETELY FILLS THE INTENDED SPACE AS ILLUSTRATED HERE:
If you want to cancel your scores from this test administration, complete A and B below. You will not receive scores for this test. No
record of this test or the cancellation will be sent to the recipients you indicated, and there will be no scores for this test on your GRE file.
Month
752369
78576-46752 • U69E5 • 10741 • UNLWEB69
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