GRE ® Chemistry Test Practice Book (PDF)

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.

www.ets.org/gre 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 [email protected].

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.

46752-78576 GRE CHEMISTRY Test Practice Book • Dr01 050509 ljg • reprint for service contract change 050609 ljg •edits dr01 051109 ljg • edits dr01 051109 mc • dr02 052609 ljg • preflight 6/5/09 mc • [New Job] 46752-114932 Drft01 7/12/16 ew • PDF Drft01 7/14/16 ew • Drft02 8/5/16 ew • PDF Drft02 8/11/16 ew • [NEW 120768] • CC15 • Dr01 5/11/17 jw • Dr02 5/25/17 hr • Dr03 6/2/17 jw 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) presenting various physical constants and a few C. Homogeneous Equilibria — Acid-base, 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 necessary chromatographic methods, thermal values are included with the question. methods, calibration of instruments This publication provides a comprehensive overview of the GRE Chemistry Test to help you get F. Environmental Applications 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 geometries, To learn more about the GRE Subject Tests, visit lattice energies, ionic radii and radius/ www.ets.org/gre. 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 divided and some interrelationships, individual and 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. consequences of band theory For example, the knowledge necessary to answer some questions classified as testing organic chemistry E. Concepts of Acids and Bases — Brønsted- may well have been acquired in analytical chemistry Lowry approaches, Lewis theory, solvent courses by some test takers. Consequently, the 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

46752-78576 GRE CHEMISTRY Test Practice Book • Dr01 050509 ljg • reprint for service contract change 050609 ljg •edits dr01 051109 ljg • edits dr01 051109 mc • dr02 052609 ljg • preflight 6/5/09 mc • [New Job] 46752-114932 Drft01 7/12/16 ew • PDF Drft01 7/14/16 ew • Drft02 8/5/16 ew • PDF Drft02 8/11/16 ew • [NEW 120768] • CC15 • Dr01 5/11/17 jw • Dr02 5/25/17 hr •Dr03 6/2/17 jw G. Chemistry of the Transition Elements — IV. Physical Chemistry (30%) Electronic structures, occurrences and recovery, physical and chemical properties A. Thermodynamics — First, second, and of the elements and their compounds, third laws, thermochemistry, ideal and real 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 radicals, carbenes, benzynes, enols in the GRE Chemistry Test, paying special 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 Test-Taking Strategies F. Special Topics — Resonance, molecular orbital theory, catalysis, acid-base The questions in the practice test illustrate the types 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

46752-78576 GRE CHEMISTRY Test Practice Book • Dr01 050509 ljg • reprint for service contract change 050609 ljg •edits dr01 051109 ljg • edits dr01 051109 mc • dr02 052609 ljg • preflight 6/5/09 mc • [New Job] 46752-114932 Drft01 7/12/16 ew • PDF Drft01 7/14/16 ew • Drft02 8/5/16 ew • PDF Drft02 8/11/16 ew • [NEW 120768] • CC15 • Dr01 5/11/17 jw • Dr02 5/25/17 hr • Dr03 6/2/17 jw The following are some general test-taking GRE Chemistry Test scores are reported on a 200 strategies you may want to consider. 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 find 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 you quickly, first answering only the questions to mark your answers to the test questions. about which you feel confident, 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 50 difficult questions if there is time. minutes available. • If you decide to change an answer, make sure To simulate how the administration will be you completely erase it and fill in the oval conducted at the test center, print the answer sheet 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 for • Your score will be determined by the number 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 time and begin marking your answers on the answer mark 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 Scoring the Practice Test it is better for you to guess at an answer than not to respond at all. The worksheet on page 51 lists the correct answers to the questions. The “Correct Response” columns are • Record all answers on your answer sheet. 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 Then, add up your correct answers and enter your a testing session to record answers on your total number of correct answers in the space labeled answer sheet. “Total Correct” at the bottom of the page. Next, use the “Total Score” conversion table on page 52 to find What Your Scores Mean the corresponding scaled score. For example, suppose you chose the correct answers to 101 questions on The number of questions you answered correctly on the test. The “Total Correct” entry in the conversion the whole test (total correct score) is converted to the table that matches 101 is 100-101 and your total total reported scaled score. This conversion ensures 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

6 Page GRE ® Chemistry Test Practice Book

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.

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TABLE OF INFORMATION

−31 Electron rest mass me = 9.11 × 10 kg

−27 Proton rest mass mp = 1.672 × 10 kg

−27 Neutron rest mass mn = 1.675 × 10 kg

Magnitude of the electron charge e = 1.60 × 10−19 C

−11 Bohr radius a0 = 5.29 × 10 m

23 −1 Avogadro constant NA = 6.02 × 10 mol

Gas constant R = 8.314 J mol−1 K−1 −1 −1 = 0.0821 L • atm mol K −1 −1 = 0.08314 L • bar mol K

Boltzmann constant k = 1.38 × 10−23 J K−1

−34 Planck constant h = 6.63 × 10 J • s −34  = h/2 p = 1.05 × 10 J • s

Speed of light c = 3.00 × 108 m s−1 = 3.00 × 1010 cm s−1

5 −2 1 bar pressure 1 bar = 1.000 × 10 N m = 1.000 × 105 Pa = 0.987 atm

1 atmosphere pressure 1 atm = 1.013 × 105 N m−2 = 1.013 × 105 Pa = 1.013 bar

4 1 Faraday constant ; = 9.65 × 10 C mol−

1 atomic mass unit (amu) 1 amu = 1.66 × 10−27 kg

1 electron volt (eV) 1 eV = 1.602 × 10−19 J

Angstrom 1 Å = 10−10 m = 10−1 nm

Volume of 1 mol of ideal = 22.4 L gas at 0° C, 1 atmosphere

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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)

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CHEMISTRY TEST 3. Of the following ions, which has the smallest Time—170 minutes radius?

130 Questions (A) K+ 2+ 1. Which of the following is the major product of the (B) Ca reaction shown above? (C) Sc3+ 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. (D) Rb (A) 2+ (E) Sr Note: Solutions are aqueous unless otherwise specified.

4. The molecular geometry of thionyl chloride, Throughout the test the following symbols have the specified definitions unless otherwise noted. SOCl2, is best described as (B)

(A) trigonal planar T M = temperature = molar (B) T-shaped P = pressure m = molal (C) tetrahedral V = volume L = liter(s) (D) trigonal pyramidal S = entropy mL = milliliter(s) (E) linear H = enthalpy g = gram(s) (C) U = internal energy kg = kilogram(s) G = Gibbs energy m = meter(s) A = Helmholtz energy nm = nanometer(s) R = gas constant atm = atmosphere(s) (D) 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) (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. (C) N2+ 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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Ê an2 ˆ 7. What is the orbital angular momentum quantum P + (V - nb ) = nRT number, l, of the electron that is most easily ËÁ 2 ¯ ˜ V 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 (E) CO2

− − + 2+ − __ MnO4 + __ I + __ H U __ Mn + __ 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. − 2+ (C) The MnO4 : Mn ratio is 3:1. (D) The H+ : I − ratio is 2:1. − − (E) The MnO4 : IO3 ratio is 1:1.

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Êan2 ˆ 7. What is the orbital angular momentum quantum P+() V - nb = nRT number, l, of the electron that is most easily ËÁ2 ¯˜ V removed when ground-state aluminum is ionized? (A) 3 9. Which of the following is the major organic product of the 6. Of the following substances, which is likely to reaction shown above? have the largest value of the coefficient a in the (B) 2 van der Waals equation of state for real gases (C) 1 (A) CH3CH2CH2CH(OH)2 (D) 0 shown above? (B) CH CH CH CHO (E) 1/2 3 2 2 (A) H2 (C) CH CH CH CH OH 3 2 2 2 (B) N 2 (D) CH CH CH CH 3 2 2 3 (C) CH4 (E) (D) NH3 (E) CO2

10. All of the following are aromatic EXCEPT − − + 2+ − __ MnO4 + __ I + __ H U __ Mn + __ IO3 + __ H2O (A)

8. When the equation shown above is balanced, which of the following is true?

− − (A) The I : IO3 ratio is 3:1. (B) − − (B) The MnO4 : I ratio is 6:5. − 2+ (C) The MnO4 : Mn ratio is 3:1. + − (C) 11. In a DNA double-helix, guanine and cytosine (D) The H : I ratio is 2:1. bases, shown above, are paired together by (E) The MnO − : IO − ratio is 1:1. 4 3 (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 most [A] [B] Initial Rate

thermodynamically stable? 0.10 M 0.30 M 1.5 × 10−4 M s−1 (A) 0.20 M 0.30 M 3.0 × 10−4 M s−1 0.20 M 0.60 M 12.0 × 10−4 M s−1

14. For the reaction A + B → C + D carried (B) out at constant temperature, the initial rates of reaction given above were found experimentally. The rate law of this reaction, expressed as a (C) function of reactant concentrations, is

(A) rate = k ([A] + [B])

(B) rate = k [A][B] (D) (C) rate = k [A]2[B] (D) rate = k [A][B]2 2 4 (E) rate = k [A] [B] (E) 15. Which of the following must be true about a binary liquid mixture that obeys Raoult’s law?

I. The partial pressure of each component 13. Under constant current electrolysis, how many at equilibrium is proportional to its mole coulombs would be required to reduce 2 mol fraction in the liquid mixture. II. The volume of the mixture is equal to the of Cu2+ to metallic copper? sum of the volumes of each component (� = 96,500 coulombs/mol) before mixing. (A) 2 III. Intermolecular interactions in the mixture (B) 48,250 are identical to intermolecular interactions in the pure components. (C) 96,500 (D) 193,000 (A) I only (E) 386,000 (B) III only (C) I and III only (D) II and III only (E) I, II, and III

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12. Of the following isomers, which is the most [A] [B] Initial Rate − 2− + 3+ 3 Cl (aq) + 4 CrO4 (aq) + 23 H (aq) → 3 HClO2(aq) + 4 Cr (aq) + 10 H2O(l) thermodynamically stable? 0.10 M 0.30 M 1.5 × 10−4 M s−1 − (A) 0.20 M 0.30 M 3.0 × 10−4 M s−1 16. In the reaction shown above, Cl (aq) behaves as 0.20 M 0.60 M 12.0 × 10−4 M s−1 (A) an acid (B) a base 14. For the reaction A + B → C + D carried (C) a catalyst (B) out at constant temperature, the initial rates of (D) an oxidizing agent (E) a reducing agent reaction given above were found experimentally.

The rate law of this reaction, expressed as a (C) function of reactant concentrations, is

(A) rate = k ([A] + [B]) 17. Elements with partially filled 4f or 5f orbitals (B) rate = k [A][B] (D) include all of the following EXCEPT (C) rate = k [A]2[B] (A) Cu (D) rate = k [A][B]2 (B) Gd 2 4 (E) rate = k [A] [B] (C) Eu (E) (D) Am 19. In the compound shown above, which hydrogen 15. Which of the following must be true about a (E) Cm is most easily abstracted in a free radical binary liquid mixture that obeys Raoult’s law? bromination reaction?

I. The partial pressure of each component O (A) 1 13. Under constant current electrolysis, how many at equilibrium is proportional to its mole (B) 2 coulombs would be required to reduce 2 mol fraction in the liquid mixture. CH CH CCH (C) 3 II. The volume of the mixture is equal to the 3 2 3 of Cu2+ to metallic copper? (D) 4 sum of the volumes of each component (E) 5 (� = 96,500 coulombs/mol) before mixing. H H (A) 2 III. Intermolecular interactions in the mixture A B (B) 48,250 are identical to intermolecular interactions (C) 96,500 in the pure components. 18. Which of the following gives the multiplicities of 20. Which of the following is the major product of the (D) 193,000 (A) I only the signals for the protons designated H and (E) 386,000 A reaction shown above? (B) III only H in the 1H NMR spectrum of the compound B (A) (C) I and III only shown above? (D) II and III only (E) I, II, and III HA HB (B)

(A) Singlet Singlet (C) (B) Triplet Doublet (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 IR (C) The entropy of the system increases. 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 region 22. The equation DH = DU + PDV is applicable of the IR spectrum (D) each element absorbs at a characteristic (A) always wavelength (B) only for constant pressure processes (E) vibrational transitions are correlated to (C) only for constant temperature processes 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 a constant temperature. Which of the following maximum for 56Fe. is true about w (work) and q (heat transfer) for (B) Nuclear binding energies have about the same this process? magnitude as chemical bond energies. (C) Nuclei have slightly less mass than the sum of w q 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 nuclei (D) < 0 > 0 together. (E) = 0 = 0 (E) When very light elements undergo exothermic fusion reactions, the released energy arises 24. What is the maximum number of phases that from an increased binding energy per can be at equilibrium with each other in a three- nucleon in the fusion products. component mixture? (A) 2 (B) 3 (C) 4 (D) 5 (E) 6

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21. Which of the following is always true of a 25. Infrared (IR) spectroscopy is useful for 27. The dissociation energy for a hydrogen-bromine 30. Which of the following is classified spontaneous process? determining certain aspects of the structure bond is defined as the change in enthalpy, DH, as a conjugate acid-base pair? of organic molecules because for which of the following reactions? (A) The process is exothermic. (A) HCl / NaOH (B) The process does not involve any work. (A) all molecular bonds absorb IR (A) 2 HBr(g) → H2(g) + Br2(l) (B) H O+ / H O (C) The entropy of the system increases. radiation 3 2 (B) HBr(g) → H+(g) + Br−(g) (D) The internal energy of the system decreases. (B) IR peak intensities are related to (C) O2 / H2O (E) The total entropy of the system plus molecular mass (C) H(g) + Br(g) → HBr(g) (D) H+ / Cl− surroundings increases. (C) most organic functional groups (D) H2(g) + Br2(l) → 2 HBr(g) (E) NaCl / NaOH absorb in a characteristic region (E) HBr(g) → H(g) + Br(g) 22. The equation DH = DU + PDV is applicable of the IR spectrum 31. An impure sample of K2O was analyzed by (D) each element absorbs at a characteristic (A) always 28. A radioactive isotope, which is used in diagnostic precipitating the potassium as the insoluble wavelength (B) only for constant pressure processes imaging, has a half-life of 6.0 hours. If a quantity tetraphenyl borate salt, KB(C H ) . The (E) vibrational transitions are correlated to 6 5 4 (C) only for constant temperature processes of this isotope has an activity of 150 mCi when it spin-spin coupling precipitate, KB(C6H5)4 had a mass of 1.57 g. (D) only for constant volume processes is delivered to a hospital, how much activity will The mass of K O in the original sample is (E) only for constant entropy processes remain 24 hours after delivery? 2 26. Which of the following statements about nuclear (mCi = microcuries) obtained from which of the following? (Molar binding energies is NOT true? 23. A system that consists of a sample of nitrogen (A) 150 mCi masses: KB(C6H5)4 = 358.3 g and K2O = 94.2 g) gas behaving as an ideal gas is compressed at a (A) Binding energy per nucleon reaches a (B) 38 mCi (1.57)(94.2) constant temperature. Which of the following maximum for 56Fe. (C) 19 mCi (A) is true about w (work) and q (heat transfer) for (358.3) (B) Nuclear binding energies have about the same (D) 9.4 mCi this process? magnitude as chemical bond energies. (E) 4.7 mCi (358.3) (C) Nuclei have slightly less mass than the sum of (B) (1.57)(94.2) w q their component nucleons. 29. The rate, r, of a zero-order chemical reaction (A) > 0 < 0 (D) The nuclei of heavy elements have more A → B can be expressed as which of the (1.57)(94.2) neutrons than protons in order to provide (C) (B) > 0 > 0 following? 2(358.3) sufficient binding energy to hold the nuclei (C) < 0 < 0 (A) r = k ln[A] (D) < 0 > 0 together. 2(1.57)(94.2) (B) r = k [A]2 (D) (E) = 0 = 0 (E) When very light elements undergo exothermic (358.3) fusion reactions, the released energy arises (C) r = k [A] from an increased binding energy per (D) r = k [A]1/2 2(358.3) 24. What is the maximum number of phases that (E) can be at equilibrium with each other in a three- nucleon in the fusion products. (E) r = k (1.57)(94.2) component mixture? (A) 2 (B) 3 (C) 4 (D) 5 (E) 6

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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)

(C)

(D)

(C)

(E)

(D)

(E)

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33. Of the following compounds, which has the 34. Of the following, which compound is in 36. Considering 0.1 M aqueous solutions of each of fastest SN1 reaction rate with H2O in acetone? equilibrium with the greatest percentage the following, which solution has the lowest pH ? of its enol isomer? (A) (A) Na2CO3 O 32. Which of the following are the major products (A) (B) Na3PO4 (C) Na S of the reaction shown above? H C H 2 3 (D) NaCl (A) (B) O (E) CH3COONa

37. Of the following compounds, which has H3C CH3

(B) the lowest melting point? (C) O (A) HCl (B) (B) AgCl

(C) CaCl2 (D) (C) O (D) CCl4 (E) SnCl4 O 38. Of the following solutions, which will have (D) (E) O the highest ionic strength? (Assume complete dissociation.) (C) (A) 0.050 M AlCl 3 O (B) 0.100 M NaCl (E) (C) 0.050 M CaCl 2 (D) 0.100 M HCl

(E) 0.050 M Ca(NO3)2

2 SO3(g) U 2 SO2(g) + O2(g) (D) 39. The K for the reaction shown above is 0.26 at P 1,000°C and 40.8 at 1,300°C. Which of the 35. In which of the following are the molecules following combinations of DH and DS are most shown above listed in order of increasing reactivity toward electrophilic aromatic plausible for this reaction at these temperatures? substitution? DH DS (A) 2 < 4 < 1 < 3

(B) 3 < 2 < 4 < 1 (A) = 0 = 0 (E) (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 Ê 1 1 ˆ H (g) + I (g) ZZZZX 2 HI(g) v R 2 2 YZZZZ = H Á 2- 2 ˜ k-1 Ë n1 n 2 ¯

40. At a given temperature, the forward rate 42. The Rydberg equation given above accurately predicts the UV-visible emission spectrum of the constant, k1, for the one-step reaction shown −7 −1 −1 hydrogen atom. A form of the Rydberg equation above is 4 × 10 M s . Given that the may also be used to predict the UV-visible −2 equilibrium constant is 1 × 10 , what is the emission for all of the following EXCEPT reverse rate constant, k ? −1 (A) hydride ion, H− (A) 8 × 10−5 M−1 s −1 (B) deuterium atom, D (B) 4 × 10−5 M−1 s −1 (C) tritium atom, T (D) helium cation, He+ (C) 4 × 10−7 M−1 s −1 (E) beryllium cation, Be3+ (D) 8 10−9 M−1 s −1 × −9 −1 −1 (E) 4 × 10 M s

pKa 1 = 2.95 pK = 6.79 CaCO (s) S° = 92.9 J K −1 mol −1 a 2 3 CaO(s) S° = 39.8 J K −1 mol −1 43. Phthalic acid, (COOH)C6H4(COOH), is a weak, −1 −1 CO2(g) S° = 213.7 J K mol diprotic acid with dissociation constants above.

The pH of an aqueous solution of potassium 41. Given the standard molar entropies listed acid phthalate, (COOH)C H (COO−K+), is above, the standard reaction entropy, DS ∞, 6 4 closest to in J K −1 mol −1, for the decomposition of calcium carbonate into calcium oxide and (A) 9.74 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 Br2 (D) (39.8 + 213.7) at standard temperature and pressure? (E) (−92.9 + 39.8 + 213.7) (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.

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k1 Ê1 1 ˆ 45. On the basis of oxidation-reduction potential, which of the H (g) + I (g) ZZZZX 2 HI(g) v R 2 2 YZZZZ =H Á2 - 2 ˜ following is most likely to occur? k-1 Ën1 n 2 ¯ (A) Al(s) + 3 NaNO3(aq) → 3 Na(s) + Al(NO3)3(aq) 40. At a given temperature, the forward rate 42. The Rydberg equation given above accurately (B) Zn(s) + 2 Ag(NO3)(aq) → 2 Ag(s) + Zn(NO3)2(aq) predicts the UV-visible emission spectrum of the constant, k1, for the one-step reaction shown (C) Pb(s) + Ca(NO3)2(aq) → Ca(s) + Pb(NO3)2(aq) −7 −1 −1 hydrogen atom. A form of the Rydberg equation above is 4 × 10 M s . Given that the may also be used to predict the UV-visible (D) Pb(s) + 2 LiNO3(aq) → 2 Li(s) + Pb(NO3)2(aq) −2 equilibrium constant is 1 × 10 , what is the emission for all of the following EXCEPT (E) Ca(s) + 2 NaNO3(aq) → 2 Na(s) + Ca(NO3)2(aq) reverse rate constant, k−1 ? − (A) hydride ion, H −5 −1 −1 (A) 8 × 10 M s (B) deuterium atom, D (B) 4 × 10−5 M−1 s−1 (C) tritium atom, T (D) helium cation, He+ (C) 4 × 10−7 M−1 s−1 46. Cobalt-60 is used in the radiation therapy of (E) beryllium cation, Be3+ (D) 8 10−9 −1 −1 cancer and can be produced by bombardment × M s −9 −1 −1 of cobalt-59 with which of the following? (E) 4 × 10 M s pK = 2.95 (A) Neutrons a1 (B) Alpha particles pK = 6.79 −1 −1 a2 CaCO3(s) S° = 92.9 J K mol (C) Beta particles 47. Which of the following are the products of the (D) X-rays reaction shown above? CaO(s) S° = 39.8 J K −1 mol −1 43. Phthalic acid, (COOH)C6H4(COOH), is a weak, (E) Gamma rays CO (g) −1 −1 2 S° = 213.7 J K mol diprotic acid with dissociation constants above. (A)

The pH of an aqueous solution of potassium 41. Given the standard molar entropies listed acid phthalate, (COOH)C H (COO−K+), is above, the standard reaction entropy, D∞S , 6 4 closest to in J K −1 mol −1, for the decomposition of (B) calcium carbonate into calcium oxide and (A) 9.74 carbon dioxide is (B) 7.00 (C) 6.79 (A) (92.9 + 39.8 + 213.7) (D) 4.87 (C) (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 Br2 (D) (39.8 + 213.7) at standard temperature and pressure? (D) (E) (−92.9 + 39.8 + 213.7) (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) (E) It is a yellow insulating solid.

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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 (D) 2.0 × 10−9 −9 (E) 4.0 × 10 (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

+• (C) y *( x ) y ( x ) dx = 0 (D) Ú -• +• (D) Ú y *()x y ()x dx = 1 -• (E) d 2 y ()x (E) 1 2 = dx

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49. At 25°C, the maximum amount of PbI2 that can 51. If y ()r is the wavefunction for a 1s electron, the average be dissolved in 1.00 L of pure water is 1.0 mmol. distance from the nucleus for the electron is equal to Assuming complete dissociation, the solubility (A) y * ()r y()r product, Ksp, for lead iodide at 25°C is 48. What is the product of the reaction shown above r * for para-cresol? −3 (B) y ()r y() rrd (A) 1.0 × 10 Ú0 −6 (A) (B) 1.0 × 10 • (C) 1.0 × 10−9 (C) y * ()r y() rrd (D) 2.0 × 10−9 Ú0 −9 (E) 4.0 × 10 (D) y * ()rrˆ y()r (B) 50. Which of the following must be true if the • (E) 4p y *() r rˆ y()r r2 dr wavefunction y(x) is normalized? Ú0 (A) y*(x ) y ( x )= 0

(C) (B) y*()()x y x = 1 52. Which of the following experimental observations 54. The anhydride of Ba(OH) is +• 2 were explained by Planck’s quantum theory? (C) y*(x ) y ( x ) dx = 0 (A) BaH2 (D) Ú (A) Blackbody radiation curves -• (B) BaOH (B) Emission spectra of diatomic molecules +• (C) Ba (D) y*()()x y x dx = 1 (C) Electron diffraction patterns Ú (D) Temperature dependence of reaction rates (D) BaO2 -• (E) (E) Pressure dependence of boiling points (E) BaO d2y() x (E) 1 2 = dx 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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− 2− − 58. Which of the following types of spectroscopy HgO + 4 I + H2O → HgI4 + 2 OH is a light-scattering technique? 55. A 0.217 g sample of HgO (molar mass = 217 g) (A) Nuclear magnetic resonance reacts with excess iodide ions according to the (B) Infrared reaction shown above. Titration of the resulting (C) Raman solution requires how many mL of 0.10 M HCl to (D) Ultraviolet-visible reach equivalence point? (E) Electron paramagnetic resonance (A) 1.0 mL (B) 10 mL 59. When a certain metal is irradiated with radiation (C) 20 mL of frequency 5.5 × 1014 s−1, electrons are (D) 50 mL ejected. If the work function of the metal is (E) 100 mL 2.9 × 10−19 J, which of the following expresses the kinetic energy (in joules) of the ejected 56. The Hamiltonian operator for a particle in a one- electrons? dimensional box, whose potential is zero inside the box and infinite outside the box, is (A) h(5.5 × 1014 s−1) − (2.9 × 10−19 J)

2 2 ˆ -= d (A) H = (B) (2.9 × 10−19 J) − h(5.5 × 1014 s−1) 2m dx 2 2 2 ˆ -= d af (B) H = + 14 −1 −19 2mR 2 df 2 p (C) h(5.5 × 10 s ) + (2.9 × 10 J)

2 2 ˆ -= d 1 2 14 1 (C) H = + kx h(5.5 ¥ 10 s - ) 2m dx 2 2 (D) (2.9 ¥ 10 -19 J) 2Ê 2 2 2 ˆ Ze 2 (D) Hˆ -= ∂ ∂ ∂ = 2+ 2 + 2 - 2m ËÁ ∂x ∂y ∂z ˜¯ r (2.9 ¥ 10 -19 J) 2 2 2 2 (E) Ê ˆ 14 -1 (E) Hˆ -= ∂ ∂ ∂ h(5.5 ¥ 10 s ) = 2 Á 2+ 2 + 2 ˜ 2mR 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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− 2− − 58. Which of the following types of spectroscopy HgO + 4 I + H2O → HgI4 + 2 OH O O is a light-scattering technique? NaOCH 55. A 0.217 g sample of HgO (molar mass = 217 g) (A) Nuclear magnetic resonance CH3 3 CH3 reacts with excess iodide ions according to the (B) Infrared CH3 CH3OH reaction shown above. Titration of the resulting (C) Raman CH3 solution requires how many mL of 0.10 M HCl to (D) Ultraviolet-visible O reach equivalence point? (E) Electron paramagnetic resonance 60. The product of the reaction shown above is produced via (A) 1.0 mL which of the following intermediates? (B) 10 mL 59. When a certain metal is irradiated with radiation (C) 20 mL of frequency 5.5 × 1014 s−1, electrons are (A) OH (D) 50 mL ejected. If the work function of the metal is (E) 100 mL 2.9 × 10−19 J, which of the following expresses + CH3 the kinetic energy (in joules) of the ejected CH3 56. The Hamiltonian operator for a particle in a one- electrons? dimensional box, whose potential is zero inside O the box and infinite outside the box, is (A) h(5.5 × 1014 s−1) − (2.9 × 10−19 J) (B) O 2 2 -= d (A) Hˆ −19 14 −1 = 2 (B) (2.9 × 10 J) − h(5.5 × 10 s ) CH 2m dx 3 + CH - 2d 2 af 3 (B) Hˆ = = + 2 2 (C) h(5.5 × 1014 s−1) + (2.9 × 10−19 J) 2mR df p OH

2 2 O ˆ -= d 1 2 14 1 (C) (C) H = + kx h(5.5¥ 10 s- ) 2m 2 2 (D) dx -19 2 2 2 2 2 (2.9¥ 10 J) CH ˆ -= Ê ∂ ∂ ∂ ˆ Ze + 3 (D) H = + + - CH2 2m ËÁ ∂x2 ∂ y 2 ∂ z 2 ¯˜ r (2.9¥ 10-19 J) 2 2 2 2 (E) Ê ˆ 14- 1 O (E) Hˆ -= ∂ ∂ ∂ h(5.5¥ 10 s ) = 2Á 2+ 2 + 2 ˜ 2mRË ∂ x ∂ y ∂ z ¯ (D)

57. The normal modes of a carbon dioxide molecule that are infrared-active include which of the following? I. Bending II. Symmetric stretching (E) O III. Asymmetric stretching − .. CH3 (A) I only CH3 (B) II only (C) III only O (D) I and III only (E) I, II, and III

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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?

(A) (B)

(B) (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 62. What is the product of the reaction shown above? II. Use of internal standards (C) Silicon carbide 61. Which of the following is the major product of the (A) III. Averaging the results from multiple samples (D) Arsenic-doped silicon reaction shown above? (E) Gallium-doped silicon (A) I only

(A) (B) II only (B) 68. Which of the following is lower (C) III only for argon than for neon? (D) I and III only (B) (C) (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 (C) volume of the buffer solution by adding water has (E) First ionization energy (D) 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 (D) (B) It significantly increases the pH. for which of the following reasons? (C) It significantly decreases the pH. (E) (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 4− (E) pKb of the conjugate base. deprotonated Y 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

water at 25°C is 30.0 atm M −1. The concentration 66. A substance that is NOT generally considered to be a toxic pollutant in water is of dissolved CO2 in a vessel pressurized with 2.0 atm of CO is (A) carbonic acid 2 (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

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k Process Work AM+ ææ1 ÆA * + M k A * + M ææÆ2 AM+ System A Adiabatic −300 J k A * æ æÆ3 products System B Nonadiabatic −200 J

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? kk[M][A] DU(J) q(J) rate = 13 . k3 + k2[M] (A) −300 0

(B) −300 −100 Which of the following is NOT consistent with this mechanism? (C) −100 −100 (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.

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k Process Work 73. Chlorofluorocarbons (CFCs) such as F CCCl AM+ ææÆ1 A* + M 3 3 are implicated in the decomposition of * k A+ MææÆ2 AM + System A Adiabatic −300 J stratospheric ozone. Which of the following

* k methods would be best suited to measurement 74. Which of the following best depicts the initial Aæ æÆ3 products System B Nonadiabatic −200 J of trace amounts (sub-ppb) of CFCs in an air nucleophilic addition step in the acid-catalyzed

hydrolysis of acetonitrile shown above? 71. The gas-phase reaction A → products is 72. System A and system B above are identical closed sample? postulated to proceed by the mechanism shown systems that undergo a change of state from the (A) above, in which A* is an activated A molecule same initial conditions (P1, V1, T1) to the same (A) Gas chromatographic separation of the air sample on a capillary column followed 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 by electron capture detection mechanism yields the rate equation state for system B? (B) Gas chromatographic separation of the air sample on a packed column followed by kk[M][A] DU(J) q(J) rate = 13 . thermal conductivity detection k3+ k 2[M] (A) −300 0 (C) Gas chromatographic separation of the air (B) (B) −300 −100 sample on a capillary column followed Which of the following is NOT consistent with by flame ionization detection this mechanism? (C) −100 −100 (D) 0 −300 (D) Conversion of the sample of the chlorinated (A) When the partial pressure of M is very high, (E) 200 0 compounds to chloride ions, followed by the reaction is first order in A. titration with Ag+ (B) When the partial pressure of M is very high, the reaction is first order overall. (E) Conversion of the sample of the chlorinated (C) When the partial pressure of M is very low, compounds to chloride ions, followed by (C) the reaction is second order overall. direct measurement of chloride with (D) When the partial pressure of M is very low, chloride selective electrode the rate is independent of the concentration of A. (E) M can be any molecule capable of transferring energy to A upon collision. (D)

(E)

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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)

(C)

(D)

(D) (E)

(E)

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77. Of the following fatty acids, which has the lowest melting point?

(A)

(B)

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

(A) (D)

(B) (E) (B)

(C)

(C) 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? (D) (A) BeCl 2 (B) MgCl (A) PbH4 < SnH4 < GeH4 < SiH4 < CH4 2 (B) PbH4 < SnH4 < CH4 < GeH4 < SiH4 (D) (C) ZnCl2 (C) CH4 < SiH4 < GeH4 < SnH4 < PbH4 (D) SCl (E) 2 (D) CH4 < PbH4 < GeH4 < SnH4 < SiH 4 (E) SnCl2 (E) GeH4 < PbH4 < SiH4 < SnH4 < CH4

79. The strongest base in liquid ammonia is (E)

(A) NH3 − (B) NH2 + (C) NH4

(D) N2H4 (E) OH−

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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)

(C)

(D)

(D) (E)

(E)

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82. Which of the following is the major organic 83. Which of the following procedures gives the compound 81. Which of the following starting materials could product of the reaction shown above? be used in a Diels-Alder reaction to prepare the shown above? bicyclic product shown above? (A) (A) (A)

(B) (B) (B)

(D) (E) (E)

(E)

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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 (B) B cubes tubes in which released electrons migrate to a 8 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 wavelength around 190 nm, which corresponds (C) C (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

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86. Redox enzyme catalysis involves the cyclic - E / RT k1 k2 k = Ae a oxidation and reduction of metal ions that have at E + S YZZZZZZZXZ ES ææÆ P + E k-1 least two stable positive oxidation states. Which 90. The rate constant of a bimolecular gas phase of the following groups of metals could be found 89. The mechanism shown above has been proposed reaction is found to follow the Arrhenius equation at the active site of redox enzymes? for the enzyme-catalyzed hydrolysis of certain shown above. Which of the following will result (A) Cu, Fe, Co biochemical compounds (substrates), where ES in a smaller rate constant? (B) Zn, Ca, Ga is an enzyme-substrate complex. Given a fixed amount of enzyme, E, which of the following (A) Reducing activation energy (C) Sr, Ga, Mg (B) Reducing temperature (D) Na, Ba, Al could be the plot of the initial rate of the production of product, P, when using varying (C) Reducing pressure (E) Mg, Li, K (D) Reducing concentrations of reactants initial concentrations of substrate, [S]0? (E) Increasing molecular speeds 87. The solid-state structures of the principal allotropes (A) of elemental boron are made up of which of the following structural units? k X (g) ææÆ 2 X(g) (A) B icosahedra 2 84. Ionizing radiation can be detected using gas-filled 12 (B) B8 cubes tubes in which released electrons migrate to a 91. If the dissociation of X2 proceeds by the (C) B octahedra collector electrode, producing a pulse. On the 6 (B) elementary process shown above, the rate of figure shown above, which region would give the (D) B4 tetrahedra change in [X] with respect to time is given by largest detector response per incident photon? (E) Chains of B atoms d []X k []X (A) A (A) = 88. All proteins absorb electromagnetic radiation of dt X (B) B [2 ] wavelength around 190 nm, which corresponds (C) C d []X to a p → p* excitation in the protein molecule. (B) = 2Xk (D) D (C) dt [2 ] (E) E In which region of the spectrum is this wavelength found? d []X (C) = k 85. Which of the following is required for both (A) X-ray dt paramagnetism and ferromagnetism? (B) Ultraviolet d []X 1/ 2 (D) = k X (A) Strong oxidizing conditions (C) Visible dt [2 ] (D) (B) Low-spin electron configuration (D) Infrared d []X 2 (C) Metallic physical properties (E) Microwave (E) = k X dt [2 ] (D) Superexchange (E) Unpaired electrons

(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

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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

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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 93. What is the stereochemistry of the carbohydrate structure 95. Which of the following is NOT true about the charge. Which of the following indicates the shown above? disaccharide lactose shown above? order, from first to last, that the peptides will (A) 2R, 3R (A) Lactose is a reducing sugar. reach the detector? (A = alanine; L = leucine; (B) 2R, 3S (B) Lactose undergoes mutarotation. G = glycine; K = lysine). (C) 2S, 3R (C) Lactose is optically active. (A) I, II, III (D) 2S, 3S (D) Lactose can be hydrolyzed to (B) I, III, II (E) Meso 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 94. The enzyme-catalyzed transformation above, which occurs in (B) number of photons emitted the citric acid cycle (tricarboxylic acid or Krebs cycle), is best (C) number of photons emitted, divided by the number of photons absorbed described as belonging to which of the following categories of 96. The compound shown above is a reactions? (D) number of excitation photons impinging on (A) triglyceride the sample, divided by the number of (A) Oxidation (B) trinucleotide photons absorbed (B) Reduction (C) tripeptide (E) fraction of excited molecules produced by (C) Nucleophilic alkyl substitution (D) trisaccharide direct excitation (D) Aldol condensation (E) triterpene (E) Hydrolysis

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99. When ferric oxide, Fe2O3, is dissolved in 100. Of the following ionic substances, which has the greatest lattice enthalpy? 6 M HNO3, which iron-containing species predominates in solution? (A) MgO (B) MgS (A) FeO − 2 (C) NaF − (B) Fe(OH)4 (D) NaCl (E) NaBr (C) Fe(OH)3 2+ (D) Fe(H2O)6 3+ (E) Fe(H2O)6

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]

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99. When ferric oxide, Fe2O3, is dissolved in 100. Of the following ionic substances, which has 102. Of the following colligative properties, which the greatest lattice enthalpy? is most practical for determining the extent of 6 M HNO3, which iron-containing species protein aggregation? predominates in solution? (A) MgO (B) MgS (A) Osmotic pressure (A) FeO − 2 (C) NaF (B) Freezing point depression (B) Fe(OH) − 4 (D) NaCl (C) Boiling point elevation 104. According to Hückel molecular orbital theory, (C) Fe(OH) (E) NaBr (D) Solvent vapor pressure lowering the secular equation above can be used to find 3 (E) Solute vapor pressure (D) Fe(H O) 2+ possible energy levels of the p-electrons in 2 6 (E) Fe(H O) 3+ (A) 2 6 y1 = 2s + 2px + 2p y + 2p z (B) y2 = 2s + 2px − 2p y − 2p z

y = 2s − 2p + 2p − 2p 3 x y z (C) 101. Which of the following reactions is best classified as an oxidative addition? y4 = 2s − 2px − 2p y − 2pz

(A) [Cr(CO) ] + Br − → [Cr(CO) Br] − + CO (D) 6 5 103. A set of hybrid sp3 orbitals for a carbon atom is (B) [PtH(CH3){P(C6H5)3}2] + P(C6H5)3 → [Pt{P(C6H5)3}3] + CH4 given above. Which of the following is NOT true − − about the orbitals? (E) (C) [Pt(NH3)Cl3] + NH3 → [Pt(NH3)2Cl2] + Cl (D) [Pt{P(C2H5)3}2HCl] + HCl → [Pt{P(C2H5)3}2(H)2Cl2] (A) The orbitals are degenerate. (E) [MnH(CO) ] + CF =CF → [Mn(CF CF H)(CO) ] (B) The set of orbitals has a tetrahedral geometry. 5 2 2 2 2 5 (C) These orbitals are constructed from a linear 105. Which of the following is(are) characteristic of

combination of atomic orbitals. mass spectrometry? (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

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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)

(B) (D)

(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

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107. Which of the following substituents is NOT an 109. The proton NMR spectrum of an aromatic 110. The fact that the infrared absorption frequency of ortho, para director in an electrophilic aromatic deuterium chloride (DCl) is shifted from that of compound, C8H8Br2, includes two methyl substitution reaction? hydrogen chloride (HCl) is due to the differences singlets. Its proton-decoupled 13C NMR in their (A) spectrum displays a total of six peaks. Of the (A) electron distribution 106. Which of the following is the major following, which structure best fits these data? rearrangement product of the reaction shown (B) (B) dipole moment above? (A) (C) force constant (D) polarizability (A) (E) reduced mass (C) 111. In the vibrational-rotational spectrum of a diatomic molecule, the R-branch of the spectrum (B) is the result of which of the following transitions? (D) (A) DJ = 0; Du = 0 (B) (E) (B) DJ = 1; Du = 0 (C) (C) DJ = 2; Du = 0 (D) DJ = 1; Du = 1 (E) DJ = 2; Du = 1 (D) 112. When an activated complex is formed from two

reactant molecules in the gas phase, it is usually (E) (C) assumed that the entropy has been lowered; that

is, ΔSǂ is less than zero. This assumption is based on which of the following?

(A) ΔUǂ is positive. (B) ΔHǂ is positive.

(D) (C) The preexponential factor A in the Arrhenius equation is always positive.

108. The reaction of terephthaloyl chloride with ethylene glycol, (D) The activated complex is ill defined and shown above, forms a transitory.

(A) polyamide (E) Forming the activated complex involves (B) polyester (E) conversion of translational and rotational (C) polyether degrees of freedom into vibrational degrees (D) polycarbonate of freedom. (E) polyurethane

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113. A student performs five titrations and obtains 114. Which of the following statements about the a 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 the of the titrated solution is 0.100 M, which of the lanthanide elements is +3 . following is true about the titration results? (B) Lanthanide complexes often have high (A) Accurate but not precise 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 with (E) There are insufficient data to determine 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) Ni(en) 2+(aq) (en = 1,2-ethylenediamine) U 3 Ni2+(aq) + 6 NH (aq) U Ni(NH ) 2+(aq) 3 3 6 2+ 10 115. The equilibrium constant for the formation of Ni(en)3 , shown above, is 10 -fold greater than the equilibrium 2+ constant for the formation of Ni(NH3)6 . 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

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113. A student performs five titrations and obtains 114. Which of the following statements about the 116. Which of the following is a true statement 119. When the Heisenberg uncertainty principle is a mean result of 0.110 M, with a standard lanthanide elements is NOT true? about optical isomerism of complexes applied to a quantum mechanical particle in the deviation of 0.001 M. If the actual concentration containing achiral ligands? lowest energy level of a one-dimensional box, (A) The most common oxidation state for the of the titrated solution is 0.100 M, which of the which of the following is true? lanthanide elements is +3 . (A) Square planar complexes can display optical following is true about the titration results? (B) Lanthanide complexes often have high isomerism only if all four ligands are (A) Momentum is known exactly, but no (A) Accurate but not precise coordination numbers (> 6) . identical. information about position can be known. (B) Precise but not accurate (C) All of the lanthanide elements react with (B) Tetrahedral complexes never display optical (B) Position is known exactly, but no information (C) Both accurate and precise aqueous acid to liberate hydrogen. isomerism. about momentum can be known. (D) Neither accurate nor precise (D) The lanthanides form stable complexes with (C) Linear complexes can display optical (C) No information about either position or (E) There are insufficient data to determine chelating oxygen ligands. isomerism when both ligands are different. momentum can be known. the accuracy and precision of the results. (E) The atomic radii of the lanthanide elements (D) Octahedral complexes of monodentate (D) Both position and momentum can be known increase across the period from La to Lu. ligands can display optical isomerism only exactly. when they have at least three different (E) Neither position nor momentum can be ligands. known exactly. (E) Trigonal bipyramidal complexes display optical isomerism when their axial ligands 2+ 2+ Ni (aq) + 3 en(aq) U Ni(en)3 (aq) (en = 1,2-ethylenediamine) differ from their equatorial ligands.

Ni2+(aq) + 6 NH (aq) U Ni(NH ) 2+(aq) 3 3 6 117. An organic compound has a distribution 115. The equilibrium constant for the formation of Ni(en) 2+ shown above, is 1010-fold greater than the equilibrium 3 , coefficient, Kp , of 2.00 between an ether and constant for the formation of Ni(NH ) 2+. The primary explanation for this large difference 3 6 water. If 10.0 g of the compound is dissolved in is termed the (A) Jahn-Teller effect 100 mL of water that is then extracted twice with (B) Tyndall effect (C) ammonia effect 100 mL portions of the ether, what fraction of the (D) crystal field effect Ê Cether ˆ (E) chelate effect compound remains in the water? Á KP = ˜ Ë C water ¯

(A) 0.111 (B) 0.200 120. A reactant, R, can produce either of two (C) 0.250 products, P1 or P2, with competing pathways, (D) 0.500 as illustrated in the reaction profile shown above. (E) 0.889 If the reaction is carried out at low temperature, which of the following best indicates the preferred 118. Exact solutions of the Schrödinger equation product and the type of control? CANNOT be obtained for a Preferred Product Control (A) simple harmonic oscillator (B) particle in a one-dimensional box (A) P Kinetic (C) rigid rotor 1 (D) hydrogen atom (B) P1 Thermodynamic (E) helium atom (C) P2 Kinetic (D) P2 Thermodynamic (E) R Thermodynamic

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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)

(E)

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Substance Wavelengths Absorbed (nm) 124. Which of the following structures represents A 400−600, 700−800 the amino acid lysine at pH 1 ? B < 400, 500−700 (A) C < 400

122. Which of the following reagents can be used 121. For the titration reaction A + B → C, where A = analyte, to convert cyclopentanol to bromocyclopentane, B = titrant, and C = product, the end point is to be detected as shown above? spectrophotometrically at 550 nm, based on the absorbance (B) information shown above. The shape of the titration curve at (A) NaBr 550 nm would most closely resemble which of the following? (B) PBr3 (C) Br2, CCl4 (A) (B) (D) N-bromosuccinimide (NBS), hn (C)

(E) Br2, H2O

(D)

123. Reduction of D-xylose with NaBH4 yields a product that is a

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

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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 3. Sn, HCl followed by NaOH

(D) 1. Na2Cr2O7, H2SO4 2. CH3CH2ONa 3. NaBH4, CH3OH

(E) 1. Na2Cr2O7, H2SO4 + 2. CH3CH2OH, H 3. H2O, HCl

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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 (A) R shown above? 2 (B) 2R

5 (C) R 125. The reaction sequence shown above can be used to prepare benzocaine from 4-nitrotoluene. Which of 2 the following reaction sequences would accomplish this synthesis? (D) 3R (A) 1. Na Cr O , H SO 7 2 2 7 2 4 (E) R + 2 2. CH3CH2OH, H

3. Sn, HCl followed by NaOH

(B) 1. NaBH4, CH3OH + 2. CH3CH2OH, H 3. Sn, HCl followed by NaOH (A) I and II (B) II and III (C) 1. H2O, HCl (C) II and IV 2. CH3CH2ONa (D) III and IV 3. Sn, HCl followed by NaOH (E) IV and V

(D) 1. Na2Cr2O7, H2SO4 2. CH3CH2ONa 3. NaBH4, CH3OH

(E) 1. Na2Cr2O7, H2SO4 + 2. CH3CH2OH, H 3. H2O, HCl

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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

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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

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?

If you finish before time is called, you may check your work on this test. (A) I (B) II (C) III

(D) IV (E) V

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A. Print and sign your full name PRINT: ______(LAST) (FIRST) (MIDDLE) in this box: SIGN: ______

6. TITLE CODE Copy this code in box 6 on 2 7 1 2 0 Copy the Test Name and Form Code in box 7 on your answer your answer sheet. Then sheet. 0 0 0 0 0 fill in the corresponding 1 1 1 1 1 ovals exactly as shown. 2 2 2 2 2 TEST NAME ______Chemistry 3 3 3 3 3 4 4 4 4 4 FORM CODE ______GR1727 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 you answer a question incorrectly. Therefore, to maximize your score, it is better for you to guess at an answer than not to respond at all. 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 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 (E) Oslo A B C D E

DO NOT OPEN YOUR TEST BOOK UNTIL YOU ARE TOLD TO DO SO.

® Educational Testing Service 50 Princeton, New Jersey 08541

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

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

52 Page GRE ® Chemistry Test Practice Book

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08541 NJ Princeton, Service, Testing Educational by 2012 ® Copyright TF212E70 • 89176-02954 Q3442/1-2/2 E E E E E E E E E E E E E E E E of cover (on back of cover (on back D E D E D E D E D E D E D E D D D D D D D D D D D D D D D D C C C C C C C C C C C C C C C C C C C C C C C B B B B B B B B B B B B B B B B B B B B B B B SHADED AREA FOR ETS USE ONLY SHADED 8. TEST BOOK SERIAL NUMBER TEST 8. 7. TEST TEST NAME 7. book) test your book) test your FORM CODE A A A A A A A of in upper right (number corner cover of front book) test your A A A A A A A A A A A A A A A A 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115

E E E E E E E E E E E E - SUBJECT TEST - SUBJECT D E D E D E D E D E D E D E D E D E D E D E D D D D D D D D D D D D . C C C C C C C C C C C C C C C C C C C C C C C book) test your of cover (on back 6. TITLE 6. CODE 0 1 2 3 4 5 6 7 8 9 B B B B B B B B B B B B B B B B B B B B B B B

A A A A A A A A A A A Item responses continued on reverse side. on reverse continued responses Item A A A A A A A A A A A A 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 choice. answer your sheet. this answer complete THEM BLANK. HERE: ILLUSTRATED E E E E E E E E E E E E AS D D E D D E D D E D D E D D E D D E D D E D D E D D E D D E D D E D 2 or HB) to C C C C C C C C C C C C C C C C C C C C C C C NUMBER - B B B B B B B B B B B B B B B B B B B B B B B ® 5. REGISTRATION 5. LEAVE PLEASE admission ticket) your (from lead (No. 0 1 2 3 4 5 6 7 8 9 A A A A A A A A A A A

A A A A A A A A A A A A IF SO, 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 THE INTENDED SPACE marks. or stray errors NEED. E E E E E E E E E E E E YOU D E D E D E D E D E D E D E D E D E D E D E D D D D D D D D D D D D to the space that corresponds in completely fill THAN C C C C C C C C C C C C C C C C C C C C C C C only) B B B B B B B B B B B B B B B B B B B B B B B NUMBER 0 1 2 3 4 5 6 7 8 9 (U.S.A. A A A A A A A A A A A

any erase Completely to Be sure black a pencil with soft, Use only A A A A A A A A A A A A FILLS AND COMPLETELY SOCIAL SECURITY 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 4. LAST FOUR DIGITS OF LAST 4. E E E E E E E E E E E E 0 1 2 3 4 5 6 7 8 9 D E D E D E D E D E D E D E D E D E D E D E D D D D D D D D D D D D Year USE INK 0 1 2 3 4 5 6 7 8 9 C C C C C C C C C C C C C C C C C C C C C C C 0 1 2 3 4 5 6 7 8 9 B B B B B B B B B B B B B B B B B B B B B B B FIND MORE RESPONSE SPACES Day 0 1 2 3 A A A A A A A A A A A MAY A

A DO NOT 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 YOU MARK IS DARK BE SURE EACH Jan. Feb. Mar. April May June July Aug. Sept. Oct. Nov. Dec. GRADUATE RECORD EXAMINATIONS GRADUATE 3. DATE OF BIRTH DATE 3. Month A B C D E F G H I J K L M N O P Q R S T U V W X Y Z Initial Middle A B C D E F G H I J K L M N O P Q R S T U V W X Y Z First Initial Name Number Room Code ZIP or Postal or Province State or Province State – Address – Letters – or Street

– Box – P. O . (given name), and name), name initial (given , first Number Center – – –

– Country City M.I. Name (Given) or Surname) First Last Name (Family City – – Enter your last name your Enter one. have initial if you middle etc. II., Jr., apostrophes, Omit spaces, Country – MAILING ADDRESS: CENTER: SIGNATURE: (Print) (Print) YOUR NAME: YOUR I J 2. L F T Z A B E K P S V X Y C D H N R U G O Q M W 1. NAME 1. 15 Name or Surname) - First (Family Last Name only

Q O 53 54 TR 147 146 145 144 143 142 141 140 139 138 137 136 135 134 133 132 131 130 129 128 127 126 125 124 123 122 121 120 119 118 117 116 E UE AH AK S AK N CMLTL FLS H ITNE SAE S LUTAE HR: . HERE: ILLUSTRATED SPACEAS INTENDED YOU THE MAY FILLS FINDMORERESPONSESPACES COMPLETELY THAN AND YOU DARK NEED. IFSO, ISPLEASE LEAVE THEM BLANK. MARK EACH SURE BE

A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A THEN TURN ANSWER SHEET ANSWER THEN TURN CERTIFICATION STATEMENT, B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B TW C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C FOR ETSUSEONLY OVER TO SIDE1. COMPLETE THE D D D D D D D D D D D D D D D D D D D SUBJECT TEST D D D D D D D D D D D D D E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E TFS SIDE 2 179 178 177 176 175 174 173 172 171 170 169 168 167 166 165 164 163 162 161 160 159 158 157 156 155 154 153 152 151 150 149 148 TCS

A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B 3R 5R 1R C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E 1W 5W 3W SIGNATURE: CERTIFICATION STATEMENT Sign anddate where indicated. agree notto disclose thecontents ofthetest Iamtakingtoday to anyone.” thatIamtheperson whosenameappears“I certify onthisanswer sheet. Ialso Please write thefollowing statement below, DONOT PRINT. 211 210 209 208 207 206 205 204 203 202 201 200 199 198 197 196 195 194 193 192 191 190 189 188 187 186 185 184 183 182 181 180 1FS 5FS 3FS

A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B 3CS 1CS 5CS C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E 6R 4R 2R 242 241 240 239 238 237 236 235 234 233 232 231 230 229 228 227 226 225 224 223 222 221 220 219 218 217 216 215 214 213 212 2W 6W 4W

A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B B C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C 6FS 4FS 2FS D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D D E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E E 6CS 4CS 2CS DATE:

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