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

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: 2p 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

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

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 1s orbital is spherically symmetrical.
b. An atomic orbital may contain zero, one, or two electrons.
c. A 2s orbital and a 2p orbital are equal in energy.
d. A 2px orbital and a 2py orbital are equal in energy.
e. A 2p 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, ml = 0, s = +½ d. n = 2, l = 1, ml = −1, s = −½
b. n = 1, l = 1, ml = 0, s = +½ e. n = 3, l = 0, ml = 0, s = −½
c. n = 2, l = 1, ml = 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 5d subshell?
a. n = 5; l = 2, ml = −3, s= ½ d. n = 5; l = 2, ml = −2, s= 1
b. n = 5; l = 2, ml = −2, s= ½ e. n = 5; l = 1, ml = 0, s= −½
c. n = 5; l = 4, ml = −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 5d 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 2s orbital?
a. There are zero nodes in a 2s orbital.
b. A 2s orbital has one spherical node.
c. A 2s orbital has one nodal plane.
d. A 2s orbital has one spherical node and one nodal plane.
e. A 2s 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 2p orbital?
a. There are zero nodes in a 2p orbital.
b. A 2p orbital has one spherical node.
c. A 2p orbital has one nodal plane.
d. A 2p orbital has one spherical node and one nodal plane.
e. A 2p 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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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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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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