GRE Chemistry Test: Practice Book

GRE ® Chemistry Test
Practice Book
This practice book contains
n one actual, full-length GRE® Chemistry Test
n test-taking strategies
Become familiar with

n test structure and content
n test instructions and answering procedures
Compare your practice test results with the performance of those

who took the test at a GRE administration.
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Table of Contents
Overview ........................................................................................................................ 3
Test Content................................................................................................................... 3
Preparing for the Test ................................................................................................... 4
Test-Taking Strategies ................................................................................................. 4
What Your Scores Mean .............................................................................................. 5
Taking the Practice Test............................................................................................... 5
Scoring the Practice Test ............................................................................................. 5
Evaluating Your Performance ..................................................................................... 6
Practice Test .................................................................................................................. 7
Worksheet for Scoring the Practice Test ................................................................. 51
Score Conversion Table ............................................................................................. 52
Answer Sheet............................................................................................................... 53
Alt text is provided for 77 of the 130 GRE® Chemistry Test questions in this practice book. However,
because of the complexity and length of the verbal descriptions that the graphics associated with some of
the questions would require, it is not practical to provide alt text for all 130 questions in this test. The
statement “No alt text” is included for each of the 53 questions for which alt text is not provided.
If you need additional accessible practice material for the GRE Chemistry Test, contact ETS Disability
Services at 1-609-771-7780 or stassd@ets.org.
Copyright © 2017 by Educational Testing Service. All rights reserved. ETS, the ETS logo, MEASURING THE POWER OF
LEARNING, GRADUATE RECORD EXAMINATIONS, and GRE are registered trademarks of Educational Testing Service
(ETS) in the United States and other countries.
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Overview I. Analytical Chemistry (15%)
The GRE® Chemistry Test consists of about 130 A. Data Acquisition and Use of Statistics —
multiple-choice questions. Testing time is 2 hours and Errors, statistical considerations
50 minutes; there are no separately-timed sections. B. Solutions and Standardization —
A periodic table is printed in the test booklet as Concentration terms, primary standards
well as a table of information (see pages 8 and 9)
C. Homogeneous Equilibria — Acid-base,
presenting various physical constants and a few
conversion factors among SI units. Whenever oxidation-reduction, complexometry
necessary, additional values of physical constants D. Heterogeneous Equilibria — Gravimetric
are printed with the text of the question. Test analysis, solubility, precipitation
questions are constructed to simplify mathematical titrations, chemical separations
manipulations. As a result, neither calculators nor E. Instrumental Methods — Electrochemical
tables of logarithms are needed. If the solution to a methods, spectroscopic methods,
problem requires the use of logarithms, the chromatographic methods, thermal
necessary values are included with the question. methods, calibration of instruments
This publication provides a comprehensive
F. Environmental Applications
overview of the GRE Chemistry Test to help you get
ready for test day. It is designed to help you: G. Radiochemical Methods — Detectors,
Applications
• Understand what is being tested
• Gain familiarity with the question types II. Inorganic Chemistry (25%)
• Review test-taking strategies
A. General Chemistry — Periodic trends,
• Understand scoring oxidation states, nuclear chemistry
• Practice taking the test
B. Ionic Substances — Lattice
To learn more about the GRE Subject Tests, visit geometries, lattice energies, ionic radii
www.ets.org/gre. and radius/ ratio effects
C. Covalent Molecular Substances — Lewis
Test Content diagrams, molecular point groups, VSEPR
concept, valence bond description
The content of the Chemistry Test emphasizes the and hybridization, molecular orbital
four fields into which chemistry has been traditionally description, bond energies, covalent and
divided and some interrelationships, individual van der Waals radii of the elements,
questions may test more than one field of chemistry. intermolecular forces
Some test takers may associate a particular question
D. Metals and Semiconductors — Structure,
with one field, whereas other test takers may have
band theory, physical and chemical
encountered the same material in a different field. For
consequences of band theory
example, the knowledge necessary to answer some
questions classified as testing organic chemistry may E. Concepts of Acids and Bases —
well have been acquired in analytical chemistry Brønsted-Lowry approaches, Lewis
courses by some test takers. Consequently, the theory, solvent system approaches
emphases of the four fields indicated in the following F. Chemistry of the Main Group Elements —
outline of material covered by the test should not be Electronic structures, occurrences and
considered definitive. recovery, physical and chemical properties
of the elements and their compounds
GRE ® Chemistry Test Practice Book 3 Page
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G. Chemistry of the Transition Elements — IV. Physical Chemistry (30%)
Electronic structures, occurrences and
recovery, physical and chemical A. Thermodynamics — First, second, and
properties of the elements and their third laws, thermochemistry, ideal and real
compounds, coordination chemistry gases and solutions, Gibbs and Helmholtz
energy, chemical potential, chemical
H. Special Topics — Organometallic
equilibria, phase equilibria, colligative
chemistry, catalysis, bioinorganic
properties, statistical thermodynamics
chemistry, applied solid-state
chemistry, environmental chemistry B. Quantum Chemistry and Applications to
Spectroscopy — Classical experiments,
III. Organic Chemistry (30%) principles of quantum mechanics, atomic
and molecular structure, molecular
A. Structure, Bonding, and Nomenclature — spectroscopy
Lewis structures, orbital hybridization,
configuration and stereochemical C. Dynamics — Experimental and theoretical
notation, conformational analysis, chemical kinetics, solution and liquid
systematic IUPAC nomenclature, dynamics, photochemistry
spectroscopy (IR and 1H and 13C NMR)
B. Functional Groups — Preparation, Preparing for the Test
reactions, and interconversions of alkanes, GRE Subject Test questions are designed to measure
alkenes, alkynes, dienes, alkyl halides, skills and knowledge gained over a long period of
alcohols, ethers, epoxides, sulfides, thiols, time. Although you might increase your scores to
aromatic compounds, aldehydes, ketones, some extent through preparation a few weeks or
carboxylic acids and their derivatives, months before you take the test, last minute cramming
amines is unlikely to be of further help. The following
C. Reaction Mechanisms — Nucleophilic information may be helpful.
displacements and addition, nucleophilic
• A general review of your college courses is
aromatic substitution, electrophilic
probably the best preparation for the test.
additions, electrophilic aromatic
However, the test covers a broad range of
substitutions, eliminations, Diels-Alder
subject matter, and no one is expected to be
and other cycloadditions
familiar with the content of every question.
D. Reactive Intermediates — Chemistry and
nature of carbocations, carbanions, free • Become familiar with the types of questions in
the GRE Chemistry Test, paying special
radicals, carbenes, benzynes, enols
attention to the directions. If you thoroughly
E. Organometallics — Preparation and understand the directions before you take the
reactions of Grignard and organolithium test, you will have more time during the test to
reagents, lithium organocuprates, and focus on the questions themselves.
other modern main group and transition
metal reagents and catalysts
F. Special Topics — Resonance,
Test-Taking Strategies
molecular orbital theory, catalysis, acid- The questions in the practice test illustrate the types
base theory, carbon acidity, aromaticity, of multiple-choice questions in the test. When you
antiaromaticity, macromolecules, lipids, take the actual test, you will mark your answers on a
amino acids, peptides, carbohydrates, separate machine-scorable answer sheet.
nucleic acids, terpenes, asymmetric
synthesis, orbital symmetry, polymers
4 Page GRE ® Chemistry Test Practice Book
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The following are some general test-taking GRE Chemistry Test scores are reported on a
strategies you may want to consider. 200 to 990 score scale in ten-point increments.
Test scores should be compared only with other
• Read the test directions carefully, and work as scores on the Chemistry Test. For example, a 750 on
rapidly as you can without being careless. For the Chemistry Test is not equivalent to a 750 on the
each question, choose the best answer from Biology Test.
the available options.
• All questions are of equal value; do not waste Taking the Practice Test
time pondering individual questions you fiind
The practice test begins on page 7. The total time
extremely difficult or unfamiliar.
that you should allow for this practice test is 2 hours
• You may want to work through the test and 50 minutes. An answer sheet is provided for
quickly, fiirst answering only the questions you to mark your answers to the test questions.
about which you feel confiident, then going It is best to take this practice test under timed
back and answering questions that require conditions. Find a quiet place to take the test and
more thought, and concluding with the most make sure you have a minimum of 2 hours and
diffiicult questions if there is time. 50 minutes available.
• If you decide to change an answer, make To simulate how the administration will be
sure you completely erase it and fiill in the conducted at the test center, print the answer sheet
oval corresponding to your desired answer. (pages 53 and 54). Then go to the back cover of
the test book (page 50) and follow the instructions
• Your score will be determined by the number for completing the identification areas of the answer
of questions you answer correctly. Questions sheet. When you are ready to begin the test, note the
you answer incorrectly or for which you mark time and begin marking your answers on the answer
no answer or more than one answer are sheet. Stop working on the test when 2 hours and 50
counted as incorrect. Nothing is subtracted minutes have elapsed.
from a score if you answer a question
incorrectly. Therefore, to maximize your
score it is better for you to guess at an answer
Scoring the Practice Test
than not to respond at all. The worksheet on page 51 lists the correct answers to
• Record all answers on your answer sheet. the questions. The “Correct Response” columns are
provided for you to mark those questions for which
Answers recorded in your test book will not
you chose the correct answer.
be counted.
Mark each question that you answered correctly.
• Do not wait until the last few minutes of a Then, add up your correct answers and enter your
testing session to record answers on your total number of correct answers in the space labeled
answer sheet. “T
the “Total Score” conversion table on page 52 to
What Your Scores Mean fiind the corresponding scaled score. For example,
suppose you chose the correct answers to 101
The number of questions you answered correctly on questions on the test. The “Total Correct” entry in
the whole test (total correct score) is converted to the the conversion table that matches 101 is 100-101
total reported scaled score. This conversion ensures and your total scaled score is 790.
that a scaled score reported for any edition of a GRE
Chemistry Test is comparable to the same scaled score
earned on any other edition of the test. Thus, equal
scaled scores on a particular test indicate essentially
equal levels of performance regardless of the test
edition taken.
GRE ® Chemistry Test Practice Book 5 Page
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It is important to realize that the conditions under
Evaluating Your Performance which you tested yourself were not exactly the same
Now that you have scored your test, you may wish as those you will encounter at a test center. It is
to compare your performance with the performance impossible to predict how different test-taking
of others who took this test. conditions will affect test performance, and this is
The data in the worksheet on page 51 are based on only one factor that may account for differences
the performance of a sample of the test takers who between your practice test scores and your actual test
took the GRE Chemistry Test in the United States. scores. By comparing your performance on this
The numbers in the column labeled “P+” on the practice test with the performance of other
worksheet indicate the percentages of examinees in individuals who took GRE Chemistry Test,
this sample who answered each question correctly. however, you will be able to determine your
You may use these numbers as a guide for strengths and weaknesses and can then plan a
evaluating your performance on each test question. program of study to prepare yourself for taking the
Interpretive data based on the scores earned by a GRE Chemistry Test under standard conditions.
recent cohort of test takers are available on the GRE
website at www.ets.org/gre/subject/scores/
understand. The interpretive data show, for selected
scaled score, the percentage of test takers who
received lower scores. To compare yourself with this
population, look at the percentage next to the scaled
score you earned on the practice test. Note that these
interpretive data are updated annually and reported on
GRE score reports.
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FORM GR1727
27
GRADUATE RECORD EXAMINATIONS®
CHEMISTRY TEST
Copyright © 2007 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.
7
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8
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TABLE OF INFORMATION
−31
Electron rest mass m = 9.11 × 10 kg
e
−27
Proton rest mass m = 1.672 × 10 kg
p
−27
Neutron rest mass m = 1.675 × 10 kg
n
−19
Magnitude of the electron charge e = 1.60 × 10 C
Bohr radius a0 = 5.29 × 10−11 m
Avogadro constant NA = 6.02 × 1023 mol−1

−1 −1
Gas constant R = 8.314 J mol K
−1 −1
= 0.0821 L atm mol K
−1 −1
= 0.08314 L bar mol K
−23
Boltzmann constant k = 1.38 × 10 J K−1
−34
Planck constant h = 6.63 × 10 Js
−34
= h/2 p = 1.05 × 10 Js
8 −1 10 −1
Speed of light c = 3.00 × 10 m s = 3.00 × 10 cm s
5 −2
1 bar pressure 1 bar = 1.000 × 10 N m
5
= 1.000 × 10 Pa
= 0.987 atm
5 −2
1 atmosphere pressure 1 atm = 1.013 × 10 N m
5
= 1.013 × 10 Pa
= 1.013 bar
4 −1
Faraday constant ; = 9.65 × 10 C mol
−27
1 atomic mass unit (amu) 1 amu = 1.66 × 10 kg
−19
1 electron volt (eV) 1 eV = 1.602 × 10 J
−10
Angstrom 1 Å = 10 m = 10−1 nm
Volume of 1 mol of ideal = 22.4 L
gas at 0 C, 1 atmosphere
GO ON TO THE NEXT PAGE.
9
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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 = temperature M = molar
P = pressure m = molal
V = volume L = liter(s)
S = entropy mL = milliliter(s)
H = enthalpy g = gram(s)
U = internal energy kg = kilogram(s)
G = Gibbs energy m = meter(s)
A = Helmholtz energy nm = nanometer(s)
R = gas constant atm = atmosphere(s)
n = number of moles J = joule(s)
s = seconds kJ = kilojoule(s)
mol = mole(s) ppm = parts per million
C = coulomb(s) Pa = Pascal(s)
V = volt(s)
Unauthorized copying or reuse of

any part of this page is illegal.
10
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3. Of the following ions, which has the
smallest radius?
+
(A) K
2+
1. Which of the following is the major product of the (B) Ca
reaction shown above? (C) Sc3+
+
(D) Rb
(A)
(E) Sr2+
4. The molecular geometry of thionyl chloride,
SOCl2 , is best described as
(B)
(A) trigonal planar
(B) T-shaped
(C) tetrahedral
(D) trigonal pyramidal
(E) linear
(C)
(D)
(E)
5. Which of the following is true of the cell

represented above?
(A) Metal M is being oxidized.
(B) Metal N is the reducing agent.
2+
(C) N ions are being oxidized.
2+
(D) M ions are being reduced.
(E) The cell potential must be zero.
2. According to IUPAC rules, what is the name
of the molecule shown above?
(A) Benzyl propanoate
(B) Phenyl propanoate
(C) Phenyl butanoate
(D) Propanoyl benzene
(E) Propyl benzoate

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an2 ˆ
ÁP + ˜ (V - nb ) = nRT 7. What is the orbital angular momentum quantum
number, l, of the electron that is most easily
ËV2¯ removed when ground-state aluminum is ionized?
6. Of the following substances, which is likely to (A) 3

have the largest value of the coefficient a in the (B) 2
van der Waals equation of state for real gases (C) 1
shown above? (D) 0
(E) 1/2
(A) H2
(B) N2
(C) CH4
(D) NH3
Ê
(E) CO2
__ MnO4 − + __ I− + __ H+ U __ Mn2+ + __ IO3− + __ H2O
8. When the equation shown above is balanced, which of the following is true?
(A) The I− : IO3 − ratio is 3:1.
(B) The MnO4 − : I− ratio is 6:5.
(C) The MnO4 − : Mn2+ ratio is 3:1.
+ −
(D) The H : I ratio is 2:1.
(E) The MnO4 − : IO3 − ratio is 1:1.

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9. Which of the following is the major organic product of the
reaction shown above?
(A) CH3CH2CH2CH(OH)2
(B) CH3CH2CH2CHO
(C) CH3CH2CH2CH2OH
(D) CH3CH2CH2CH3
(E)
10. All of the following are aromatic EXCEPT

(A)
(B)
11. In a DNA double-helix, guanine and

(C) cytosine
bases, shown above, are paired together by
(A) covalent bonds
(D) (B) hydrogen bonds
(C) peptide bonds
(D) hyperconjugation
(E) (E) π-stacking

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12. Of the following isomers, which is the [A] [B] Initial Rate
most thermodynamically stable? 0.10
−4
M 0.30 M 1.5 × 10 M s−1
(A)
0.20
−4
M 0.30 M 3.0 × 10 M s−1
0.20
−4 −1
M 0.60 M 12.0 × 10 M s
14. For the reaction A + B → C + D carried out at
(B) constant temperature, the initial rates of reaction
given above were found experimentally. The
rate law of this reaction, expressed as a function
(C)
of reactant concentrations, is
(D) (A) rate = k ([A] + [B])
(B) rate = k [A][B]
2
(C) rate = k [A] [B]
(D) rate = k [A][B]2
(E)
(E) rate = k [A]2[B]4
15. Which of the following must be true about a
binary liquid mixture that obeys Raoult’s law?
13. Under constant current electrolysis, how many
coulombs would be required to reduce 2 mol I. The partial pressure of each component
at equilibrium is proportional to its
of Cu2+ to metallic copper? mole fraction in the liquid mixture.
(�= 96,500 coulombs/mol) II. The volume of the mixture is equal to
(A) 2 the sum of the volumes of each
(B) 48,250 component before mixing.
(C) 96,500 III. Intermolecular interactions in the mixture
(D) 193,000 are identical to intermolecular interactions
(E) 386,000 in the pure components.
(A) I only
(B) III only
(C) I and III only
(D) II and III only
(E) I, II, and III

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3 Cl−(aq) + 4 CrO42−(aq) + 23 H+(aq) → 3 HClO2(aq) + 4 Cr3+(aq) + 10 H2O(l)
16. In the reaction shown above, Cl−(aq) behaves as

(A) an acid
(B) a base
(C) a catalyst
(D) an oxidizing agent
(E) a reducing agent
17. Elements with partially filled 4f or 5f orbitals

include all of the following EXCEPT
(A) Cu
(B) Gd
(C) Eu
(D) Am 19. In the compound shown above, which hydrogen
(E) Cm is most easily abstracted in a free radical
bromination reaction?
O (A) 1
(B) 2
CH3CH2CCH3 (C) 3
(D) 4
(E) 5
HA HB
18. Which of the following gives the multiplicities of

20. Which of the following is the major product of the
the signals for the protons designated HA and reaction shown above?
HB in the 1H NMR spectrum of the compound
shown above? (A)
HA HB (B)
(A) Singlet Singlet
(B) Triplet Doublet (C)
(C) Septet Singlet
(D) Quartet Triplet (D)
(E) Quartet Singlet
(E)

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21. Which of the following is always true of a 25. Infrared (IR) spectroscopy is useful for
spontaneous process? determining certain aspects of the structure
of organic molecules because
(A) The process is exothermic.
(B) The process does not involve any work. (A) all molecular bonds absorb
(C) The entropy of the system increases. IR radiation
(D) The internal energy of the system decreases. (B) IR peak intensities are related to
(E) The total entropy of the system plus molecular mass
surroundings increases. (C) most organic functional groups
absorb in a characteristic
22. The equation DH = DU + PDV is applicable region of the IR spectrum
(D) each element absorbs at a
(A) always
characteristic wavelength
(B) only for constant pressure processes
(E) vibrational transitions are correlated
(C) only for constant temperature processes
to spin-spin coupling
(D) only for constant volume processes
(E) only for constant entropy processes
26. Which of the following statements about nuclear
binding energies is NOT true?
23. A system that consists of a sample of nitrogen
gas behaving as an ideal gas is compressed at a (A) Binding energy per nucleon reaches
constant temperature. Which of the following is 56
a maximum for Fe.
true about w (work) and q (heat transfer) for this (B) Nuclear binding energies have about the same
process? magnitude as chemical bond energies.
(C) Nuclei have slightly less mass than the sum
w q of their component nucleons.
(A) >0 <0 (D) The nuclei of heavy elements have more
(B) >0 >0 neutrons than protons in order to provide
(C) <0 <0 sufficient binding energy to hold the
(D) <0 >0 nuclei together.
(E) =0 =0 (E) When very light elements undergo
exothermic fusion reactions, the released
24. What is the maximum number of phases that energy arises from an increased binding
can be at equilibrium with each other in a three- energy per nucleon in the fusion products.
component mixture?
(A) 2
(B) 3
(C) 4
(D) 5
(E) 6

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27. The dissociation energy for a hydrogen-bromine 30. Which of the following is
bond is defined as the change in enthalpy, DH, classified as a conjugate acid-
for which of the following reactions? base pair?
(A) 2 HBr(g) → H2(g) + Br2(l) (A) HCl / NaOH
+
(B) HBr(g) → H+(g) + Br−(g) (B) H3O / H2O
(C) H(g) + Br(g) → HBr(g) (C) O2 / H2O
(D) H2(g) + Br2(l) → 2 HBr(g) (D) H+ / Cl−
(E) HBr(g) → H(g) + Br(g) (E) NaCl / NaOH
28. A radioactive isotope, which is used in diagnostic 31. An impure sample of K2O was analyzed
imaging, has a half-life of 6.0 hours. If a quantity by precipitating the potassium as the
of this isotope has an activity of 150 mCi when it insoluble tetraphenyl borate salt, KB(C6H5)4
is delivered to a hospital, how much activity will . The precipitate, KB(C6H5) 4 had a mass of
remain 24 hours after delivery?
(mCi = microcuries) 1.57 g. The mass of K2O in the original
sample is
(A) 150 mCi obtained from which of the following? (Molar
(B) 38 mCi
(C) 19 mCi masses: KB(C6H5)4 = 358.3 g and K2O = 94.2 g)
(D) 9.4 mCi
(E) 4.7 mCi (A) (1.57)(94.2)
(358.3)
29. The rate, r, of a zero-order chemical reaction (B) (358.3)
A → B can be expressed as which of the (1.57)(94.2)
following?
(A) r = k ln[A] (C) (1.57)(94.2)
2(358.3)
(B) r = k [A]2
(C) r = k [A] (D) 2(1.57)(94.2)
(D) r = k [A]1/2 (358.3)
(E) r=k
(E) 2(358.3)
(1.57)(94.2)

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33. Of the following compounds, which has the
fastest SN1 reaction rate with H2O in
acetone?
(A)
32. Which of the following are the major products
of the reaction shown above?
(A)
(B)
(B)
(C)
(D)
(C)
(E)
(D)
(E)

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34. Of the following, which compound is in 36. Considering 0.1 M aqueous solutions of each of
equilibrium with the greatest the following, which solution has the lowest pH ?
percentage of its enol isomer? (A) Na2CO3
O (B) Na3PO4
(A)
(C) Na2S
H3C H
(D) NaCl
(B) O (E) CH3COONa
H3C CH3 37. Of the following compounds, which has

the lowest melting point?
(C) O (A) HCl
(B) AgCl
(C) CaCl2
(D) O (D) CCl4
(E) SnCl4
O
38. Of the following solutions, which will have
(E) O the highest ionic strength? (Assume complete
dissociation.)
(A) 0.050 M AlCl3
O (B) 0.100 M NaCl
(C) 0.050 M CaCl2
(D) 0.100 M HCl
(E) 0.050 M Ca(NO3)2
2 SO3(g) U 2 SO2(g) + O2(g)
39. The KP for the reaction shown above is 0.26 at

1,000°C and 40.8 at 1,300°C. Which of the
35. In which of the following are the molecules
shown above listed in order of increasing following combinations of DH and DS are most
reactivity toward electrophilic aromatic plausible for this reaction at these temperatures?
substitution?
DHDS
(A) 2<4<1<3
(B) 3<2<4<1 (A) =0 =0
(C) 3<4<2<1 (B) >0 >0
(D) 4<2<1<3 (C) >0 <0
(E) 4<3<1<2 (D) <0 >0
(E) <0 <0

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k1 ˆ
H2(g) + I2(g) YZZZZZZZX 2 HI(g) Ê 1 1
v=R 2
k H ËÁ n - n 2¯ ˜
-1 1 2
40. At a given temperature, the forward rate 42. The Rydberg equation given above accurately
constant, k1, for the one-step reaction predicts the UV-visible emission spectrum of the
shown above is 4 × 10−7 M−1 s−1. Given
hydrogen atom. A form of the Rydberg equation
may also be used to predict the UV-visible
that the equilibrium constant is 1 × 10−2, emission for all of the following EXCEPT
(A) hydride ion, H−
what is the reverse rate constant, k−1 ?
(A) 8 × 10−5 M−1 s−1 (B) deuterium atom, D
(B) 4 × 10−5 M−1 s−1 (C) tritium atom, T
(C) 4 × 10−7 M−1 s−1 (D) helium cation, He+
(D) 8 × 10−9 M−1 s−1 (E) beryllium cation, Be3+
(E) 4 × 10−9 M−1 s−1
pKa 1 = 2.95
−1 −1 pKa 2 = 6.79
CaCO3(s) S° = 92.9 J K mol
−1 −1
CaO(s) S° = 39.8 J K mol 43. Phthalic acid, (COOH)C6H4(COOH), is a weak,
−1 −1 diprotic acid with dissociation constants above.
CO2(g) S° = 213.7 J K mol
The pH of an aqueous solution of potassium
41. Given the standard molar entropies listed
above, the standard reaction entropy, DS ∞ acid phthalate, (COOH)C6H4(COO−K+), is
−1 −1 closest to
, in J K mol , for the
decomposition of calcium carbonate (A) 9.74
into calcium oxide and carbon dioxide is (B) 7.00
(C) 6.79
(A) (92.9 + 39.8 + 213.7) (D) 4.87
(B) (−92.9 − 39.8 − 213.7) (E) 2.95
(C) (−92.9 − 39.8 + 213.7) 44. Which of the following is true for
(D) (39.8 + 213.7) Br2 at standard temperature and
(E) (−92.9 + 39.8 + 213.7) pressure?
(A) It is a colorless gas.
(B) It is a red-brown volatile liquid.
(C) It is a colorless volatile liquid.
(D) It is a yellow metallic solid.
(E) It is a yellow insulating solid.


20
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45. On the basis of oxidation-reduction potential, which of the
following is most likely to occur?
(A) Al(s) + 3 NaNO3(aq) → 3 Na(s) + Al(NO3)3(aq)
(B) Zn(s) + 2 Ag(NO3)(aq) → 2 Ag(s) + Zn(NO3)2(aq)
(C) Pb(s) + Ca(NO3)2(aq) → Ca(s) + Pb(NO3)2(aq)
(D) Pb(s) + 2 LiNO3(aq) → 2 Li(s) + Pb(NO3)2(aq)
(E) Ca(s) + 2 NaNO3(aq) → 2 Na(s) + Ca(NO3)2(aq)
46. Cobalt-60 is used in the radiation therapy

of cancer and can be produced by
bombardment of cobalt-59 with which of
the following?
(A) Neutrons
(B) Alpha particles 47. Which of the following are the products of the
(C) Beta particles reaction shown above?
(D) X-rays
(E) Gamma rays (A)
(B)
(C)
(D)
(E)

21
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49. At 25°C, the maximum amount of PbI2 that can
be dissolved in 1.00 L of pure water is 1.0 mmol.
Assuming complete dissociation, the solubility
product, Ksp, for lead iodide at 25°C is
48. What is the product of the reaction shown above
for para-cresol? (A) 1.0 × 10−3
−6
(A) (B) 1.0 × 10
(C) 1.0 × 10−9
−9
(D) 2.0 × 10
(E) 4.0 × 10−9
(B)
50. Which of the following must be true if the
wavefunction y(x) is normalized?
(A) y *( x ) y ( x ) = 0
(C)
(B) y *(x ) y (x ) = 1
+•
(D)
(C) Ú y *( x ) y ( x ) dx = 0
-•
+•
(D) Ú y *(x ) y (x ) dx = 1
-•
2
(E) d y (x ) =
(E) 1
2
dx

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51. If y (r ) is the wavefunction for a 1s electron, the average
distance from the nucleus for the electron is equal to
(A) y * (r) y (r )
(B) Ú0r y *(r)y(r ) d r

(C) Ú0• y * (r)y (r ) d r
(D) y * (r ) rˆ y(r )
(E) 4p Ú0• y *(r ) rˆ y(r ) r 2 dr
52. Which of the following experimental observations 54. The anhydride of Ba(OH)2 is
were explained by Planck’s quantum theory?
(A) BaH2
(A) Blackbody radiation curves (B) BaOH
(B) Emission spectra of diatomic molecules
(C) Ba
(C) Electron diffraction patterns
(D) Temperature dependence of reaction rates (D) BaO2
(E) Pressure dependence of boiling points (E) BaO
53. The +1 oxidation state is more stable than the

+3 oxidation state for which group 13 element?
(A) B
(B) Al
(C) In
(D) Ga
(E) Tl

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HgO + 4 I− + H2O → HgI42− + 2 OH−
24
55. A 0.217 g sample of HgO (molar mass = 217 g)
reacts with excess iodide ions according to the
reaction shown above. Titration of the resulting
solution requires how many mL of 0.10 M HCl to
reach equivalence point?
1.0
(A) mL
(B) 10 mL
(C) 20 mL
(D) 50 mL
(E) 100 mL
56. The Hamiltonian operator for a particle in a

one - dimensional box, whose potential is zero
inside the box and infinite outside the box, is
2 2
ˆ -= d
2
(A) H = 2m dx
ˆ -= 2 d2 af
2mR 2 df
2
(B) H = + p
ˆ -=2 d2 1 2
2
(C) H = 2m dx + 2 kx
ˆ -=2 Ê ∂ 2 ∂2 ∂2 ˆ Ze
2
(D) H = Á 2 + 2 + 2 ˜ -
2m
Ë ∂x ∂y ∂z ¯ r
2 2 2 2
ˆ -= Ê ∂ ∂ ∂ ˆ
(E) H = + 2 + 2˜
2m 2 Á 2
R Ë ∂x ∂y ∂z ¯
57. The normal modes of a carbon dioxide molecule
that are infrared-active include which of the
following?
I. Bending
II. Symmetric stretching
III. Asymmetric stretching
(A) I only
(B) II only
(C) III only
(D) I and III only
(E) I, II, and III

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58. Which of the following types of spectroscopy is a
light-scattering technique?
(A) Nuclear magnetic resonance
(B) Infrared
(C) Raman
(D) Ultraviolet-visible
(E) Electron paramagnetic resonance
59. When a certain metal is irradiated with radiation of

frequency 5.5 × 1014 s−1, electrons are ejected. If the
work function of the metal is
2.9 × 10−19 J, which of the following expresses the
kinetic energy (in joules) of the ejected electrons?
(A) h(5.5 × 1014 s−1) − (2.9 × 10−19 J)
−19 14 −1
(B) (2.9 × 10 J) − h(5.5 × 10 s )
(C) h(5.5 × 1014 s−1) + (2.9 × 10−19 J)
h(5.5 ¥ 1014 s -1 )
(D)
(2.9 ¥ 10-19 J)
-19
(E) (2.9 ¥ 10 J)
14 -1
h(5.5 ¥ 10 s )
www.diako.ir
O O
CH NaOCH3
3
CH3 CH3OH CH3
CH3
O
60. The product of the reaction shown above is produced via

which of the following intermediates?
(A) OH
+
CH3
CH3
O
(B) O
CH3
+ CH3
OH
(C) O
CH
+ 3
CH2
O
(D)
(E) O
..− CH3
CH3

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62. What is the product of the reaction shown above?
61. Which of the following is the major product of the (A)
reaction shown above?
(B)
(A)
(C)
(B)
(D)
(C)
(D)
(E)
(E)

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63. Which of the following procedures tend(s) to 67. Which of the following is an n-type
minimize the influence of random errors on semiconductor?
measured results?
(A) Silicon
I. Signal averaging (B) Diamond
II. Use of internal standards (C) Silicon carbide
III. Averaging the results from multiple samples (D) Arsenic-doped silicon
(E) Gallium-doped silicon
(A) I only
(B) II only
68. Which of the following is lower
(C) III only
for argon than for neon?
(D) I and III only
(E) I, II, and III (A) Melting point
(B) Boiling point
64. A buffer is made from equal concentrations of a (C) Polarizability
weak acid and its conjugate base. Doubling the (D) Heat of vaporization
volume of the buffer solution by adding water has (E) First ionization energy
what effect on its pH ?
69. For EDTA titrations, the analyte solution and the
(A) It has little effect.
titrant solution are both buffered at the same pH
(B) It significantly increases the pH.
for which of the following reasons?
(C) It significantly decreases the pH.
(D) It changes the pH asymptotically to the I. The conditional formation constant is
pKa of the acid. affected by pH.
(E) It changes the pH asymptotically to the II. The fraction of EDTA in the fully
pKb of the conjugate base. deprotonated Y4− form varies with pH.
III. When EDTA reacts to form a metal
65. Which of the following is the most common +
complex, H is a product in most cases.
naturally-occurring form in which silicon is
found? (A) I only
(B) I and II only
(A) Metallic element (C) I and III only
(B) Sulfide (D) II and III only
(C) Fluoride (E) I, II, and III
(D) Oxide
(E) Nitride 70. The Henry’s law constant for CO2 dissolved in
−1
water at 25°C is 30.0 atm M . The
66. A substance that is NOT generally considered to
be a toxic pollutant in water is concentration of dissolved CO2 in a vessel
pressurized with 2.0 atm of CO2 is
(A) carbonic acid
(B) a halogenated hydrocarbon (A) 1.5 M
(C) lead (B) 0.15 M
(D) mercury (C) 0.067 M
(E) cadmium (D) 0.015 M
(E) 0.0067 M

27
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k1 * Process Work
A+MææÆA +M
* k2 System A Adiabatic −300 J
A +MææÆA+M
* k3
System B Nonadiabatic −200 J
A ææÆ products
71. The gas-phase reaction A → products is 72. System A and system B above are identical closed
postulated to proceed by the mechanism shown systems that undergo a change of state from the
above, in which A* is an activated A molecule same initial conditions (P1, V1, T1) to the same
and M is a chemically inert gas. Assuming the final conditions (P2, V2, T2), but by a different
steady-state approximation for A*, this process. What are DU and q for the change in
mechanism yields the rate equation state for system B?
k k [M][A] DU(J) q(J)
rate = 1 3 .
k3 + k2 [M] (A) −300 0
(B) −300 −100
Which of the following is NOT consistent with
(C) −100 −100
this mechanism?
(D) 0 −300
(A) When the partial pressure of M is very high, (E) 200 0
the reaction is first order in A.
(B) When the partial pressure of M is very high,
the reaction is first order overall.
(C) When the partial pressure of M is very low,
the reaction is second order overall.
(D) When the partial pressure of M is very low,
the rate is independent of the concentration
of A.
(E) M can be any molecule capable of
transferring energy to A upon collision.

28
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73. Chlorofluorocarbons (CFCs) such as F3CCCl3
are implicated in the decomposition of
stratospheric ozone. Which of the following
methods would be best suited to measurement 74. Which of the following best depicts the initial
of trace amounts (sub-ppb) of CFCs in an air nucleophilic addition step in the acid-catalyzed
sample? hydrolysis of acetonitrile shown above?
(A) Gas chromatographic separation of the (A)

air sample on a capillary column
followed by electron capture detection
(B) Gas chromatographic separation of the air
sample on a packed column followed by
thermal conductivity detection
(C) Gas chromatographic separation of the
(B)
air sample on a capillary column
followed by flame ionization detection
(D) Conversion of the sample of the chlorinated
compounds to chloride ions, followed by
titration with Ag+
(E) Conversion of the sample of the chlorinated
compounds to chloride ions, followed by (C)
direct measurement of chloride with
chloride selective electrode
(D)
(E)

29
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75. Which of the following is the hemiacetal
intermediate in the reaction shown above?
76. What is the major product of an E2 reaction of
(A) the compound shown above?
(A)
(B)
(B)
(C)
(C)
(D)
(D)
(E)
(E)

30
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77. Of the following fatty acids, which has the lowest melting point?
(A)
(B)
(C)
(D)
(E)
78. Of the following compounds, which is LEAST 80. Which of the following lists the hydrides of
likely to behave as a Lewis acid? group-14 elements in order of thermal
stability, from lowest to highest?
(A) BeCl2
(A) PbH4 < SnH4 < GeH4 < SiH4 < CH4
(B) MgCl2
(B) PbH4 < SnH4 < CH4 < GeH4 < SiH4
(C) ZnCl2
(C) CH4 < SiH4 < GeH4 < SnH4 < PbH4
(D) SCl2 (D) CH4 < PbH4 < GeH4 < SnH4 < SiH4
(E) SnCl2 (E) GeH4 < PbH4 < SiH4 < SnH4 < CH4
79. The strongest base in liquid ammonia is

(A) NH3
(B) NH2−
+
(C) NH4
(D) N2H4
−
(E) OH

31
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82. Which of the following is the major organic
81. Which of the following starting materials could product of the reaction shown above?
be used in a Diels-Alder reaction to prepare the
bicyclic product shown above? (A)
(A)
(B)
(B)
(C)
(C)
(D)
(D)
(E)
(E)

32
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83. Which of the following procedures gives the compound
shown above?
(A)
(B)
(C)
(D)
(E)

33
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86. Redox enzyme catalysis involves the cyclic
oxidation and reduction of metal ions that have
at least two stable positive oxidation states.
Which of the following groups of metals could
be found at the active site of redox enzymes?
(A) Cu, Fe, Co
(B) Zn, Ca, Ga
(C) Sr, Ga, Mg
(D) Na, Ba, Al
(E) Mg, Li, K
87. The solid-state structures of the principal

allotropes of elemental boron are made up of
which of the following structural units?
(A) B12 icosahedra
84. Ionizing radiation can be detected using gas-filled
tubes in which released electrons migrate to a (B) B8 cubes
collector electrode, producing a pulse. On the (C) B6 octahedra
figure shown above, which region would give the (D) B4 tetrahedra
largest detector response per incident photon? (E) Chains of B atoms
(A) A
88. All proteins absorb electromagnetic radiation of
(B) B
(C) C wavelength around 190 nm, which corresponds
(D) D to a p → p* excitation in the protein molecule.
(E) E In which region of the spectrum is this
wavelength found?
85. Which of the following is required for both (A) X-ray
paramagnetism and ferromagnetism? (B) Ultraviolet
(A) Strong oxidizing conditions (C) Visible
(B) Low-spin electron configuration (D) Infrared
(C) Metallic physical properties (E) Microwave
(D) Superexchange
(E) Unpaired electrons

34
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k1 k
E + S YZZZZZZZX ES ææÆ2 P +
k = Ae - E a / RT
k
E -1
90. The rate constant of a bimolecular gas phase
89. The mechanism shown above has been proposed reaction is found to follow the Arrhenius equation
for the enzyme-catalyzed hydrolysis of certain
shown above. Which of the following will result
biochemical compounds (substrates), where ES
in a smaller rate constant?
is an enzyme-substrate complex. Given a fixed
amount of enzyme, E, which of the following (A) Reducing activation energy
could be the plot of the initial rate of the (B) Reducing temperature
production of product, P, when using varying (C) Reducing pressure
initial concentrations of substrate, [S]0 ? (D) Reducing concentrations of reactants
(E) Increasing molecular speeds
(A)
k
X2(g) ææÆ 2 X(g)
91. If the dissociation of X2 proceeds by the

(B) elementary process shown above, the rate of
change in [X] with respect to time is given by
d [ X] k[X]
(A) dt = [X2 ]
(C) d [ X]
(B) dt = 2k [X2 ]
d [ X]
(C) =k
dt
d [ X] 1/ 2
(D) (D) dt = k [X2 ]
d [ X]
(E) = k [X2
2
] dt
(E)
92. The compound shown above is AZT, a drug

used in the treatment of acquired immune
deficiency syndrome (AIDS). What is the total
number of stereoisomers for this compound?
(A) 2
(B) 4
(C) 6
(D) 8
(E) 10

35
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93. What is the stereochemistry of the carbohydrate
structure shown above?
(A) 2R, 3R
(B) 2R, 3S
(C) 2S, 3R
(D) 2S, 3S
(E) Meso
94. The enzyme-catalyzed transformation above, which occurs in

the citric acid cycle (tricarboxylic acid or Krebs cycle), is best
described as belonging to which of the following categories of
reactions?
(A) Oxidation
(B) Reduction
(C) Nucleophilic alkyl substitution
(D) Aldol condensation
(E) Hydrolysis

36
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AAK ALLLG AGGLLGGL
I II III
97. A peptide digest yields the three polypeptides

listed above. The three peptides are separated
using capillary electrophoresis at a pH (above 3)
at which each peptide has the same total positive
95. Which of the following is NOT true about the charge. Which of the following indicates the
disaccharide lactose shown above? order, from first to last, that the peptides will
(A) Lactose is a reducing sugar. reach the detector? (A = alanine; L = leucine; G
(B) Lactose undergoes mutarotation. = glycine; K = lysine).
(C) Lactose is optically active. (A) I, II, III
(D) Lactose can be hydrolyzed to
(B) I, III, II
monosaccharides with H2O/H2SO4. (C) II, I, III
(E) Lactose has a 1,1¢ -a- glycosidic linkage. (D) II, III, I
(E) III, II, I
98. In fluorescence spectroscopy, the quantum yield

(Φf ) is best defined as the
(A) rate of fluorescence emission
(B) number of photons emitted
(C) number of photons emitted, divided by
the number of photons absorbed
96. The compound shown above is a
(D) number of excitation photons impinging on
(A) triglyceride the sample, divided by the number of
(B) trinucleotide photons absorbed
(C) tripeptide (E) fraction of excited molecules produced
(D) trisaccharide by direct excitation
(E) triterpene

37
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99. When ferric oxide, Fe2O3, is dissolved in 6 100. Of the following ionic substances, which has
M HNO3, which iron-containing species the greatest lattice enthalpy?
predominates in solution? (A) MgO
− (B) MgS
(A) FeO2
(C) NaF
(B) Fe(OH)4 − (D) NaCl
(C) Fe(OH)3 (E) NaBr
(D) Fe(H2O)62+
(E) Fe(H2O)63+
101. Which of the following reactions is best classified as an oxidative addition?

(A) [Cr(CO)6] + Br − → [Cr(CO)5Br] − + CO
(B) [PtH(CH3){P(C6H5)3}2] + P(C6H5)3 → [Pt{P(C6H5)3}3] + CH4
− −
(C) [Pt(NH3)Cl3] + NH3 → [Pt(NH3)2Cl2] + Cl
(D) [Pt{P(C2H5)3}2HCl] + HCl → [Pt{P(C2H5)3}2(H)2Cl2]
(E) [MnH(CO)5] + CF2=CF2 → [Mn(CF2CF2H)(CO)5]

38
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102. Of the following colligative properties, which
is most practical for determining the extent of
protein aggregation?
(A) Osmotic pressure
(B) Freezing point depression
(C) Boiling point elevation 104. According to Hückel molecular orbital theory,
(D) Solvent vapor pressure lowering the secular equation above can be used to find
(E) Solute vapor pressure possible energy levels of the p-electrons in
(A)
y1 = 2s + 2px + 2py + 2pz
y2 = 2s + 2px − 2py − 2pz (B)
y3 = 2s − 2px + 2py − 2pz
(C)
y4 = 2s − 2px − 2py − 2pz
(D)
3
103. A set of hybrid sp orbitals for a carbon atom is
given above. Which of the following is NOT true
about the orbitals?
(E)
(A) The orbitals are degenerate.
(B) The set of orbitals has a tetrahedral geometry. 105. Which of the following is(are) characteristic of
(C) These orbitals are constructed from a linear mass spectrometry?
combination of atomic orbitals.
(D) The four electrons in these orbitals can form I. Analyte molecules are converted to gaseous
s bonds with other atoms. ions.
(E) Each hybrid orbital may hold four electrons. II. The ions are separated according to their
mass-to-charge ratio.
III. In addition to compound identification, mass
spectra can be utilized to determine precise
isotopic masses and isotopic ratios.
(A) II only
(B) I and II only
(C) I and III only
(D) II and III only
(E) I, II, and III

39
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107. Which of the following substituents is NOT an
ortho, para director in an electrophilic aromatic
substitution reaction?
(A)
106. Which of the following is the major
rearrangement product of the reaction shown (B)
above?
(A)
(C)
(D)
(B)
(E)
(C)
(D)
(E)
108. The reaction of terephthaloyl chloride with ethylene

glycol, shown above, forms a
(A) polyamide
(B) polyester
(C) polyether
(D) polycarbonate
(E) polyurethane

40
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109. The proton NMR spectrum of an aromatic 110. The fact that the infrared absorption frequency of
compound, C8H8Br2, includes two methyl deuterium chloride (DCl) is shifted from that of
13
hydrogen chloride (HCl) is due to the differences
singlets. Its proton-decoupled C NMR in their
spectrum displays a total of six peaks. Of the
(A) electron distribution
following, which structure best fits these data?
(B) dipole moment
(A) (C) force constant
(D) polarizability
(E) reduced mass
111. In the vibrational-rotational spectrum of a

diatomic molecule, the R-branch of the spectrum
is the result of which of the following transitions?
(A) DJ = 0; Du = 0
(B)
(B) DJ = 1; Du = 0
(C) DJ = 2; Du = 0
(D) DJ = 1; Du = 1
(E) DJ = 2; Du = 1
112. When an activated complex is formed from two

reactant molecules in the gas phase, it is usually
(C) assumed that the entropy has been lowered; that
is, Sǂ is less than zero. This assumption is
based on which of the following?
(A) Uǂ is positive.
(B) Hǂ is positive.
(D) (C) The preexponential factor A in the
Arrhenius equation is always positive.
(D) The activated complex is ill defined
and transitory.
(E) (E) Forming the activated complex involves

conversion of translational and rotational
degrees of freedom into vibrational
degrees of freedom.

41
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113. A student performs five titrations and obtains a 114. Which of the following statements about the
mean result of 0.110 M, with a standard lanthanide elements is NOT true?
deviation of 0.001 M. If the actual concentration
(A) The most common oxidation state for
of the titrated solution is 0.100 M, which of the
the lanthanide elements is +3 .
following is true about the titration results?
(B) Lanthanide complexes often have
(A) Accurate but not precise high coordination numbers (> 6) .
(B) Precise but not accurate (C) All of the lanthanide elements react with
(C) Both accurate and precise aqueous acid to liberate hydrogen.
(D) Neither accurate nor precise (D) The lanthanides form stable complexes
(E) There are insufficient data to determine with chelating oxygen ligands.
the accuracy and precision of the results. (E) The atomic radii of the lanthanide elements
increase across the period from La to Lu.
Ni2+(aq) + 3 en(aq) U Ni(en)32+(aq) (en = 1,2-ethylenediamine)

Ni2+(aq) + 6 NH3(aq) U Ni(NH3)62+(aq)
115. The equilibrium constant for the formation of Ni(en)32+ , shown above, is 1010-fold greater than the
equilibrium constant for the formation of Ni(NH3)62+. The primary explanation for this large difference
is termed the
(A) Jahn-Teller effect
(B) Tyndall effect
(C) ammonia effect
(D) crystal field effect
(E) chelate effect

42
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116. Which of the following is a true statement 119. When the Heisenberg uncertainty principle is
about optical isomerism of complexes applied to a quantum mechanical particle in the
containing achiral ligands? lowest energy level of a one-dimensional box,
which of the following is true?
(A) Square planar complexes can display
optical isomerism only if all four ligands (A) Momentum is known exactly, but no
are identical. information about position can be known.
(B) Tetrahedral complexes never display (B) Position is known exactly, but no information
optical isomerism. about momentum can be known.
(C) Linear complexes can display optical (C) No information about either position
isomerism when both ligands are different. or momentum can be known.
(D) Octahedral complexes of monodentate (D) Both position and momentum can be known
ligands can display optical isomerism only exactly.
when they have at least three different (E) Neither position nor momentum can
ligands. be known exactly.
(E) Trigonal bipyramidal complexes display
optical isomerism when their axial ligands
differ from their equatorial ligands.
117. An organic compound has a distribution
coefficient, Kp , of 2.00 between an ether and

water. If 10.0 g of the compound is dissolved in
100 mL of water that is then extracted twice

with
100 mL portions of the ether, what fraction of

Ê
the compound remains in the water? Á K =
Cether ˆ
˜
Ë P C water ¯ 120. A reactant, R, can produce either of two products,
(B) 0.111 P1 or P2, with competing pathways, as illustrated
(C) 0.200 in the reaction profile shown above. If the reaction
(D) 0.250 is carried out at low temperature, which of the
(E) 0.500 following best indicates the preferred product and
(F) 0.889 the type of control?
Preferred Product Control
118. Exact solutions of the Schrödinger equation
CANNOT be obtained for a
(A) P1 Kinetic
(A) simple harmonic oscillator (B) P1 Thermodynamic
(B) particle in a one-dimensional box
(C) P2 Kinetic
(C) rigid rotor
(D) hydrogen atom (D) P2 Thermodynamic
(E) helium atom (E) R Thermodynamic

43
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Substance Wavelengths Absorbed (nm)
A 400−600, 700−800
B < 400, 500−700
C < 400
121. For the titration reaction A + B → C, where A = analyte, B =

titrant, and C = product, the end point is to be detected
spectrophotometrically at 550 nm, based on the absorbance
information shown above. The shape of the titration curve at
550 nm would most closely resemble which of the following?
(A) (B)
(C) (D)
(E)

44
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124. Which of the following structures represents
the amino acid lysine at pH 1 ?
(A)
122. Which of the following reagents can be used

to convert cyclopentanol to bromocyclopentane,
as shown above? (B)
(A) NaBr
(B) PBr3
(C) Br2, CCl4
(D) N-bromosuccinimide (NBS), hn (C)
(E) Br2, H2O
(D)
(E)
123. Reduction of D-xylose with NaBH4 yields

a product that is a
(A) racemic mixture
(B) single pure enantiomer
(C) mixture of two diastereomers in equal
amounts
(D) mixture of two diastereomers in unequal
amounts
(E) meso compound

45
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125. The reaction sequence shown above can be used to prepare benzocaine from 4-nitrotoluene. Which
of the following reaction sequences would accomplish this synthesis?
(A) 1. Na2Cr2O7, H2SO4
2. CH3CH2OH, H+
3. Sn, HCl followed by NaOH
(B) 1. NaBH4, CH3OH
2. CH3CH2OH, H+
(C) 1. H2O, HCl
2. CH3CH2ONa
(D) 1. Na2Cr2O7, H2SO4
2. CH3CH2ONa
3. NaBH4, CH3OH
(E) 1. Na2Cr2O7, H2SO4
2. CH3CH2OH, H+
3. H2O, HCl

46
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127. What is the limiting high-temperature molar heat
capacity at constant volume (CV) of a gas-phase
diatomic molecule?
126. Which two of the following are the propagation
steps in the free-radical chlorination of methane 3
shown above? (A) 2 R
(B) 2R
5
(C) 2 R
(D) 3R
7
(E) 2 R
(A) I and II
(B) II and III
(C) II and IV
(D) III and IV
(E) IV and V

47
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128. The reaction energy diagram for the electrophilic bromination of benzene with Br2 and FeBr3 is shown above.
Which position on the diagram corresponds to the species shown below?
(A) I
(B) II
(C) III
(D) IV
(E) V

48
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129. Of the following atoms, which 130. Which of the following is a primary standard for
has the lowest electron affinity? use in standardizing bases?
(A) F (A) Ammonium hydroxide
(B) Si (B) Sulfuric acid
(C) O (C) Acetic acid
(D) Ca (D) Potassium hydrogen phthalate
(E) Br (E) Silver nitrate
If you finish before time is called, you may check your work on this test.
49
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NOTE: To ensure prompt processing of test results, it is important that you fill in the blanks exactly as directed.
I SUBJECT TEST
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in this box: (LAST) (FIRST) (MIDDLE)
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your answer sheet. Then 0 0 0 0 0
sheet.
fill in the corresponding
Chemistry
1 1 1 1 1
ovals exactly as shown. 2 2 2 2 2 TEST NAME
3 3 3 3 3 FORM CODE GR1727
4 4 4 4 4 ____________________________________
5 5 5 5 5
6 6 6 6 6
7 7 7 7 7
8 8 8 8 8
9 9 9 9 9
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 the number of questions you answer correctly. Questions you answer incorrectly or
for which you mark no answer or more than one answer are counted as incorrect. Nothing is subtracted from a score if
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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
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Example: Sample Answer
What city is the capital of France? A B C D E CORRECT ANSWER

(A) Rome PROPERLY MARKED
A B C D E
(B) Paris
A B C D E
(C) London
A B C D E IMPROPER MARKS
(D) Cairo
A B C D E
(E) Oslo
DO NOT OPEN YOUR TEST BOOK UNTIL YOU ARE TOLD TO DO SO.
Educational Testing Service

50 Princeton, New Jersey 08541
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Worksheet for the GRE Chemistry Test, Form GR1727
Answer Key and Percentages* of Test Takers Answering Each Question Correctly
QUESTION CORRECT QUESTION CORRECT QUESTION CORRECT

P+ P+ P+
Number Answer RESPONSE Number Answer RESPONSE Number Answer RESPONSE
1 D 74 46 A 67 91 B 37
2 E 45 47 E 48 92 D 47
3 C 71 48 A 72 93 D 52
4 D 40 49 E 34 94 A 67
5 A 81 50 D 68 95 E 54
6 D 46 51 E 37 96 C 79
7 C 62 52 A 63 97 A 65
8 B 41 53 E 40 98 C 55
9 C 47 54 E 54 99 E 39
10 D 62 55 C 65 100 A 30
11 B 86 56 A 61 101 D 25
12 B 92 57 D 56 102 A 49
13 E 49 58 C 61 103 E 66
14 D 82 59 A 58 104 D 29
15 E 30 60 E 65 105 E 70
16 E 71 61 C 65 106 C 46
17 A 98 62 E 73 107 C 46
18 E 87 63 D 41 108 B 76
19 D 68 64 A 82 109 B 63
20 C 39 65 D 90 110 E 54
21 E 52 66 A 84 111 D 36
22 B 73 67 D 54 112 E 44
23 A 45 68 E 77 113 B 76
24 D 19 69 E 19 114 E 61
25 C 95 70 C 68 115 E 53
26 B 53 71 D 42 116 D 43
27 E 26 72 B 69 117 A 43
28 D 78 73 A 37 118 E 76
29 E 80 74 B 59 119 E 47
30 B 93 75 C 86 120 A 54
31 C 53 76 A 56 121 D 36
32 D 40 77 E 63 122 B 40
33 A 40 78 D 52 123 E 36
34 E 55 79 B 66 124 D 76
35 C 39 80 A 62 125 A 58
36 D 36 81 B 72 126 C 70
37 A 35 82 A 67 127 E 14
38 A 68 83 A 56 128 C 58
39 B 52 84 E 45 129 D 86
40 B 59 85 E 74 130 D 45
41 E 90 86 A 89
42 A 66 87 A 28
43 D 53 88 B 72
44 B 73 89 A 72
45 B 46 90 B 70
Total Correct:
Total Scaled:
* The numbers in the P+ column indicate the percentages of test takers in the United States who answer each question correctly.
GRE ® Chemistry Test Practice Book 51

Page
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Score Conversion for the GRE Chemistry Test, Form GR1727
Total Score
Total Correct Scaled Score Total Correct Scaled Score
74 640
130 980 72-73 630
128-129 970 70-71 620
127 960 68-69 610
126 950 66-67 600
125 940 64-65 590

123-124 930 62-63 580
122 920 60-61 570
120-121 910 58-59 560
118-119 900 56-57 550
117 890 53-55 540

115-116 880 51-52 530
113-114 870 49-50 520
112 860 47-48 510
110-111 850 44-46 500
108-109 840 42-43 490

107 830 39-41 480
105-106 820 37-38 470
103-104 810 34-36 460
102 800 32-33 450
100-101 790 29-31 440

98-99 780 26-28 430
96-97 770 23-25 420
95 760 20-22 410
93-94 750 18-19 400
91-92 740 15-17 390

90 730 12-14 380
88-89 720 10-11 370
86-87 710 7-9 360
84-85 700 6 350
83 690 4-5 340

81-82 680 2-3 330
79-80 670 1 310
77-78 660 0 300
75-76 650

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2
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I I I I I I I I I I I I I I I I I
6 29 52 75 98
02954
ABCDE ABCDE ABCDE ABCDE ABCDE
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J J J J J J J J J J J J J J J J J
89176
KKKKKKKKKKKKKKK K K
8 A B C D E 31 A B C D E 54 A B C D E 77 A B C D E 100 A B C D E
4
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L L L L L L L L L L L L L L L L L
MMMMMMMMMMMMMMM M M
NNNNNNNNNNNNNNN N N
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O O 12 A B C D E 35 A B C D E 58 A B C D E 81 A B C D E 104 A B C D E
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Bohr radius a0 = 5.29 × 10−11 m

Avogadro constant NA = 6.02 × 1023 mol−1

GO ON TO THE NEXT PAGE.

Note: Solutions are aqueous unless otherwise specified.

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5. Which of the following is true of the cell

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6. Of the following substances, which is likely to (A) 3

__ MnO4 − + __ I− + __ H+ U __ Mn2+ + __ IO3− + __ H2O

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10. All of the following are aromatic EXCEPT

11. In a DNA double-helix, guanine and

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16. In the reaction shown above, Cl−(aq) behaves as

17. Elements with partially filled 4f or 5f orbitals

18. Which of the following gives the multiplicities of

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H3C CH3 37. Of the following compounds, which has

2 SO3(g) U 2 SO2(g) + O2(g)

39. The KP for the reaction shown above is 0.26 at

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46. Cobalt-60 is used in the radiation therapy

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(B) Ú0r y *(r)y(r ) d r

(E) 4p Ú0• y *(r ) rˆ y(r ) r 2 dr

53. The +1 oxidation state is more stable than the

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56. The Hamiltonian operator for a particle in a

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59. When a certain metal is irradiated with radiation of

(A) h(5.5 × 1014 s−1) − (2.9 × 10−19 J)

(C) h(5.5 × 1014 s−1) + (2.9 × 10−19 J)

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60. The product of the reaction shown above is produced via

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(A) Gas chromatographic separation of the (A)

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79. The strongest base in liquid ammonia is

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MnO4 − + I− + H+ U Mn2+ + IO3− + H2O