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Test Bank For Organic Chemistry, 5th Edition

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    Organic Chemistry FIFTH EDITION Maitland Jones, Jr., Steven A. Fleming Thomas A. Gray THE SAGE COLLEGES Ekaterina N. Kadnikova GUSTAVUS ADOLPHUS COLLEGE Alan J. Kennan COLORADO STATE UNIVERSITY TEST BANK

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    Preface v Chapter 1 | Atoms and Molecules; Orbitals and Bonding 1 Chapter 2 | Alkanes 28 Chapter 3 | Alkenes and Alkynes 59 Chapter 4 | Stereochemistry 90 Chapter 5 | Rings 126 Chapter 6 | Substituted Alkanes: Alkyl Halides, Alcohols, Amines, Ethers, Thiols, and Thioethers 154 Chapter 7 | Substitution Reactions: The SN2 and SN1 Reactions 182 Chapter 8 | Elimination Reactions: The E1 and E2 Reactions 208 Chapter 9 | Analytical Chemistry: Spectroscopy 240 Chapter 10 | Electrophilic Additions to Alkenes 280 Chapter 11 | More Additions to pi Bonds 319 Chapter 12 | Radical Reactions 361 Chapter 13 | Dienes and the Allyl System: 2 p Orbitals in Conjugation 398 Chapter 14 | Aromaticity 435 Chapter 15 | Substitution Reactions of Aromatic Compounds 465 Chapter 16 | Carbonyl Chemistry 1: Addition Reactions 506 Chapter 17 | Carboxylic Acids 557 Chapter 18 | Derivatives of Carboxylic Acids: Acyl Compounds 598 Chapter 19 | Carbonyl Chemistry 2: Reactions at the alpha Position 639 Chapter 20 | Carbohydrates 697 Chapter 21 | Special Topic: Bioorganic Chemistry 721 CONTENTS iii

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    Chapter 22 | Special Topic: Amino Acids and Polyamino Acids (Peptides and Proteins) 740 Chapter 23 | Special Topic: Reactions Controlled by Orbital Symmetry 758 Chapter 24 | Special Topic: Intramolecular Reactions and Neighboring Group Participation 784 iv • CONTENTS

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    that assess the material to be learned at the appropriate level, and (c) enable instructors to accurately judge stu- dents’ mastery of the material—what they know, what they don’t know, and to what degree—based on the assessment outcomes. Accurate assessments of student mastery allow instructors to focus on areas where stu- dents need the most help. HOW DOES IT WORK? The test bank authors listed the learning objectives from each chapter that they believed are the most important for students to learn. The author then developed ques- tions designed to test students’ knowledge of a particular learning objective. By asking students questions that vary in both type and level of difficulty, instructors can gather different types of evidence, which will allow them to more effectively assess how well students understand specific concepts. Six Question Types: 1. Remembering questions—test declarative knowl- edge, including textbook definitions and relation- ships between two or more pieces of information. Can students recall or remember the information in the same form it was learned? 2. Understanding questions—pose problems in a con- text different from the one in which the material was learned, requiring students to draw from their declar- ative and/or procedural understanding of important concepts. Can students explain ideas or concepts? 3. Applying questions—ask students to draw from their prior experience and use critical-thinking skills to take part in qualitative reasoning about the real world. Can students use learned information in another task or situation? When was the last time you were pleased with the con- sistency and quality of the assessment supplements that come with introductory texts? If you are like most pro- fessors, you probably find that these assessment pack- ages do not always meet your needs. To address this issue, Norton has collaborated with Valerie Shute (Flor- ida State University) and Diego Zapata-Rivera (Educa- tional Testing Services) to develop a methodology for delivering high-quality, valid, and reliable assessment supplements through our test banks and extensive suite of support materials. WHY A NEW APPROACH? In evaluating the test banks that accompany introductory texts, we found four substantive problem areas associated with the questions: 1. Test questions were misclassified in terms of type and difficulty. 2. The prevalence of low-level and factual questions misrepresented the goals of the course. 3. Topics were unevenly distributed: Trivial topics were tested via multiple items, while important concepts were not tested at all. 4. Links to course topics were too general, thus pre- venting diagnostic use of the item information. STUDENT COMPETENCIES AND EVIDENCE-CENTERED DESIGN In December 2007, we conducted a focus group with the brightest minds in educational testing to create a new model for assessment. A good assessment tool needs to (a) define what students need to know and the level of knowledge and skills expected, (b) include test items PREFACE v

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    vi • PREFACE or confusing material is included, and no slang expres- sions are used. In developing the questions, every effort has been made to eliminate bias (e.g., race, gender, cul- tural, ethnic, regional, handicap, age) to require specific knowledge of material studied, not of general knowl- edge or experience. This ensures accessibility and validity. KEY TO THE QUESTION METADATA Each question in the Test Bank is tagged with five pieces of information designed to help instructors create the most ideal mix of questions for their quiz or exam. These tags are: ANS: This is the correct answer for each question. Or, in the case of some short answer questions, a pos- sible correct answer to the given question. DIF: This is the difficulty assigned to the problem. Problems have been classified as Easy, Medium, or Difficult. REF: This is the section in the textbook from which a question is drawn. OBJ: This is the learning objective that the question is designed to test. MSC: This is the knowledge type (see above) the ques- tion is designed to test. 4. Analyzing questions—test students’ ability to break down information and see how different elements relate to each other and to the whole. Can students distinguish among the different parts? 5. Evaluating questions—ask students to assess infor- mation as a whole and frame their own argument. Can students justify a stand or decision? 6. Creating questions—pose questions or objectives that prompt students to put elements they have learned together into a coherent whole to generate new ideas. Can students create a new product or point of view based on data? Three Difficulty Levels: 1. Easy questions—require a basic understanding of the concepts, definitions, and examples. 2. Medium questions— direct students to use critical thinking skills, to demonstrate an understanding of core concepts independent of specific textbook examples, and to connect concepts across chapters. 3. Difficult questions—ask students to synthesize text- book concepts with their own experience, making analytical inferences about biological topics and more. Each question measures and explicitly links to a spe- cific competency and is written with clear, concise, and grammatically correct language that suits the difficulty level of the specific competency being assessed. To ensure the validity of the questions, no extraneous, ambiguous,

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    1 • CHAPTER 1 Calculate formal charge Multiple Choice: 13–15, 18 Analyze resonance forms for stability Multiple Choice: 19 Identify resonance structures Multiple Choice: 20–24 Construct molecular orbital diagrams Multiple Choice: 25 Short Answer: 21–23 Apply rules for molecular orbital construction Multiple Choice: 26–30, 32 Identify types of bond cleavage Multiple Choice: 31 Short Answer: 26 Understand Lewis acids and bases Multiple Choice: 33 Short Answer: 28–31 Apply rules and properties for atomic orbitals Short Answer: 3 Draw Lewis structures Short Answer: 9–13 Draw resonance forms Short Answer: 15, 17, 18, 20 Analyze resonance forms Short Answer 16, 19 Apply thermodynamics of bond formation Short Answer: 25, 27 LEARNING OBJECTIVES Understand properties of atomic orbitals Multiple Choice: 1 Short Answer: 6, 24 Evaluate trends in IP, EA in periodic table Multiple Choice: 2 Determine atomic orbital structure Multiple Choice: 3 Apply rules for quantum numbers Multiple Choice: 4, 5 Short Answer: 7 Understand the rules for quantum mechanics Multiple Choice: 6 Short Answer: 1, 2, 5 Apply rules and properties for atomic orbitals Short Answer: 3 Construct electronic configuration using rules for quantum mechanics Short Answer: 8 Derive nodes based on quantum numbers Multiple Choice: 7–9 Apply rules for Lewis structures Multiple Choice: 10, 16 Determine polarity based on 3D structure, bond dipoles Multiple Choice: 11 Short Answer: 14 Determine a dipole moment from a structure Multiple Choice: 12, 17 Chapter 1: Atoms and Molecules; Orbitals and Bonding

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    2 • CHAPTER 1 MULTIPLE CHOICE 1. Which of the following statements about atomic orbitals is false ? a. A 1 s orbital is spherically symmetrical. b. An atomic orbital may contain zero, one, or two electrons. c. A 2 s orbital and a 2 p orbital are equal in energy. d. A 2 p x orbital and a 2 p y orbital are equal in energy. e. A 2 p orbital is not spherically symmetrical. ANS: C DIF: Easy REF: 1.1 OBJ: Understand properties of atomic orbitals MSC: Remembering 2. Which of the following statements is true? a. Ionization potential decreases going across a row left to right. b. Ionization potential increases going down a group. c. Electron affinity increases going across a row left to right. d. Electron affinity increases going down a group. e. Atoms with high ionization potentials have correspondingly high electron affinities. ANS: C DIF: Easy REF: 1.2 OBJ: Evaluate trends in IP, EA in periodic table MSC: Remembering 3. What is the total number of occupied p orbitals in a neutral phosphorus atom? a. 2 d. 9 b. 3 e. 12 c. 6 ANS: C DIF: Easy REF: 1.2 OBJ: Determine atomic orbital structure MSC: Analyzing 4. Which one of the following sets of quantum numbers is impossible? a. n = 1, l = 0, m l = 0, s = + ½ d. n = 2, l = 1, m l = − 1, s = − ½ b. n = 1, l = 1, m l = 0, s = + ½ e. n = 3, l = 0, m l = 0, s = − ½ c. n = 2, l = 1, m l = 1, s = + ½ ANS: B DIF: Easy REF: 1.2 OBJ: Apply rules for quantum numbers MSC: Applying 5. Which of these sets of quantum numbers would define an electron in the 5 d subshell? a. n = 5; l = 2, m l = − 3, s = ½ d. n = 5; l = 2, m l = − 2, s = 1 b. n = 5; l = 2, m l = − 2, s = ½ e. n = 5; l = 1, m l = 0, s = − ½ c. n = 5; l = 4, m l = − 2, s = –½ ANS: B DIF: Easy REF: 1.2 OBJ: Apply rules for quantum numbers MSC: Applying

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    3 • CHAPTER 1 6. The rule or principle that states that the electronic state with the greatest number of unpaired spins will have the lowest energy is called a. the Pauli principle d. Hund’s rule b. the aufbau principle e. the octet rule c. the Heisenberg uncertainty principle ANS: D DIF: Easy REF: 1.2 OBJ: Understand the rules for quantum mechanics MSC: Remembering 7. d -orbitals have two nodal planes. How many spherical nodes will a 5 d orbital contain? a. 1 d. 4 b. 2 e. 5 c. 3 ANS: B DIF: Difficult REF: 1.2 OBJ: Derive nodes based on quantum numbers MSC: Analyzing 8. Which of the following statements accurately describes the node(s) in a 2 s orbital? a. There are zero nodes in a 2 s orbital. b. A 2 s orbital has one spherical node. c. A 2 s orbital has one nodal plane. d. A 2 s orbital has one spherical node and one nodal plane. e. A 2 s orbital has two spherical nodes. ANS: B DIF: Medium REF: 1.2 OBJ: Derive nodes based on quantum numbers MSC: Analyzing 9. Which of the following statements accurately describes the node(s) in a 2 p orbital? a. There are zero nodes in a 2 p orbital. b. A 2 p orbital has one spherical node. c. A 2 p orbital has one nodal plane. d. A 2 p orbital has one spherical node and one nodal plane. e. A 2 p orbital has two spherical nodes. ANS: C DIF: Medium REF: 1.2 OBJ: Derive nodes based on quantum numbers MSC: Analyzing

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    4 • CHAPTER 1 10. Which of the Lewis structures shown below is incorrect ? a. d. b. e. c. ANS: D DIF: Medium REF: 1.3 OBJ: Apply rules for Lewis structures MSC: Analyzing 11. Indicate which of the species shown are expected to have a net dipole moment. a. d. b. e. c. ANS: A DIF: Difficult REF: 1.3 OBJ: Determine polarity based on 3D structure, bond dipoles MSC: Analyzing

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    5 • CHAPTER 1 12. Which of the following Lewis structures shows an incorrectly drawn bond dipole? a. d. b. e. c. ANS: A DIF: Easy REF: 1.3 OBJ: Determine a dipole moment from a structure MSC: Analyzing 13. In which of the following Lewis structures does the nitrogen atom have a formal charge of 1+? a. d. b. e. c. ANS: B DIF: Easy REF: 1.3 OBJ: Calculate formal charge MSC: Applying

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    6 • CHAPTER 1 14. What is the formal charge on the oxygen atom in each of the following Lewis structures? a. A : 0, B : 1–, C : 1+ b. A : 1+, B : 1–, C : 0 c. A : 1–, B : 1+, C : 0 d. A : 1–, B : 1–, C : 1– e. A : 1+, B : 1+, C : 1– ANS: B DIF: Easy REF: 1.3 OBJ: Calculate formal charge MSC: Applying 15. Which of the following Lewis structures contains an oxygen atom with a 1+ formal charge? a. d. b. e. c. ANS: D DIF: Easy REF: 1.3 OBJ: Calculate formal charge MSC: Applying 16. Which of the following structures is the best Lewis structure for hypochlorous acid, HOCl? a. d. b. e. c. ANS: A DIF: Medium REF: 1.3 OBJ: Apply rules for Lewis structures MSC: Analyzing

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    7 • CHAPTER 1 17. Which of the following molecules has a net dipole moment? a. d. b. e. c. ANS: A DIF: Medium REF: 1.3 OBJ: Determine a dipole moment from a structure MSC: Applying 18. In which of the following structures does the carbon atom have a formal charge that is not zero? a. d. b. e. Both c and d c. ANS: C DIF: Medium REF: 1.3 OBJ: Calculate formal charge MSC: Applying

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    8 • CHAPTER 1 19. Which of the following resonance forms would be expected to be the most important contributor for the anionic species? a. d. b. e. c. ANS: B DIF: Medium REF: 1.4 OBJ: Analyze resonance forms for stability MSC: Analyzing 20. Which of the following arrow conventions is used to show the relationship of two chemical species as resonance structures? a. d. b. e. Both a and b c. ANS: A DIF: Easy REF: 1.4 OBJ: Identify resonance structures MSC: Remembering

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    9 • CHAPTER 1 21. Which two of the following structures are equivalent resonance contributors? a. A and B d. A and D b. A and C e. All the structures are equivalent. c. B and C ANS: B DIF: Easy REF: 1.4 OBJ: Identify resonance structures MSC: Analyzing 22. Which of the following pairs are not related as resonance structures? a. b. c. d. e. ANS: C DIF: Medium REF: 1.4 OBJ: Identify resonance structures MSC: Analyzing

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    10 • CHAPTER 1 23. Which of the following pairs are related as resonance structures? All nonzero formal charges are shown. a. b. c. d. e. ANS: B DIF: Medium REF: 1.4 OBJ: Identify resonance structures MSC: Analyzing

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