Solution Manual for Organic Chemistry: Principles and Mechanisms, 2nd Edition

Name: Solution Manual for Organic Chemistry: Principles and Mechanisms, 2nd Edition
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Solution Manual for Organic Chemistry: Principles and Mechanisms, 2nd Edition is your ultimate textbook solutions guide, providing answers to the most difficult questions.

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Organic Chemistry:
Principles and Mechanisms
Second Edition
Joel M. Karty
Michelle Boucher
UTICA COLLEGE
Cliff Coss
NORTHERN ARIZONA UNIVERSITY
Stephen Pruett
JEFFERSON COMMUNITY AND TECHNICAL COLLEGE
’S GUIDE

Preface v
Introduction ix
Chapter 1: Atomic and Molecular Structure 1
Interchapter A: Nomenclature: The Basic System for Naming Simple Organic Compounds—Alkanes,
Haloalkanes, Nitroalkanes, Cycloalkanes, and Ethers 6
Chapter 2: Three-Dimensional Geometry, Intermolecular Interactions, and Physical Properties 9
Chapter 3: Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals 14
Interchapter B: Naming Alkenes, Alkynes, and Benzene Derivatives 18
Chapter 4: Isomerism 1: Conformers and Constitutional Isomers 21
Chapter 5: Isomerism 2: Chirality, Enantiomers, and Diastereomers 27
Interchapter C: Stereochemistry in Nomenclature: R and S Configurations about Asymmetric Carbons and Z and E
Configurations about Double Bonds 33
Chapter 6: The Proton Transfer Reaction: An Introduction to Mechanisms, Thermodynamics, and Charge
Stability 36
Chapter 7: An Overview of the Most Common Elementary Steps 42
Interchapter D: Molecular Orbital Theory, Hyperconjugation, and Chemical Reactions 48
Interchapter E: Naming Compounds with a Functional Group That Calls for a Suffix 1: Alcohols, Amines,
Ketones, and Aldehydes 51
Chapter 8: An Introduction to Multistep Mechanisms: SN1 and E1 Reactions and Their Comparisons to SN 2 and E2
Reactions 54
Chapter 9: Nucleophilic Substitution and Elimination Reactions 1: Competition among SN 2, SN 1, E2, and E1
Reactions 59
Interchapter F: Naming Compounds with a Functional Group That Calls for a Suffix 2: Carboxylic Acids and
Their Derivatives 66
Chapter 10: Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis 68
Chapter 11: Electrophilic Addition to Nonpolar Bonds 1: Addition of a Brønsted Acid 74
Chapter 12: Electrophilic Addition to Nonpolar Bonds 2: Reactions Involving Cyclic Transition States 78
Chapter 13: Organic Synthesis 1: Beginning Concepts in Designing Multistep Synthesis 83
Chapter 14: Orbital Interactions 2: Extended Systems, Conjugation, and Aromaticity 89
Chapter 15: Structure Determination 1: Ultraviolet–Visible and Infrared Spectroscopies 94
Chapter 16: Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry 100
Chapter 17: Nucleophilic Addition to Polar Bonds 1: Addition of Strong Nucleophiles 107
Chapter 18: Nucleophilic Addition to Polar Bonds 2: Weak Nucleophiles and Acid and Base Catalysis 112
Chapter 19: Organic Synthesis 2: Intermediate Topics in Synthesis Design, and Useful Redox and Carbon–Carbon
Bond-Forming Reactions 118
Chapter 20: Nucleophilic Addition–Elimination Reactions 1: The General Mechanism Involving Strong
Nucleophiles 123
Chapter 21: Nucleophilic Addition–Elimination Reactions 2: Weak Nucleophiles 127
Chapter 22: Aromatic Substitution 1: Electrophilic Aromatic Substitution on Benzene; Useful Accompanying
Reactions 132
Chapter 23: Aromatic Substitution 2: Reactions of Substituted Benzenes and Other Rings 136
Chapter 24: The Diels–Alder Reaction and Other Pericyclic Reactions 141
Chapter 25: Reactions Involving Free Radicals 146
Interchapter G: Fragmentation Pathways in Mass Spectrometry 150
Chapter 26: Polymers 152
Additional Resources 157
Sample Syllabi 161
Problem Correlation Table 177

(73()2"//+
I met Joel Karty in 2005 at a conference. At that point, I had been teaching organic chemistry for more than
10 years. On the basis of students’ success at other institutions and their reports of scores on standardized exams
such as the PCAT, MCAT, and DAT, I felt that I was successful as an organic instructor. I was also content—
though not necessarily happy—with the textbook I was using.
Joel and I spent hours at that conference talking about his work in progress, a new textbook for organic chemistry
that would be structured around mechanism types rather than functional groups. I was a hard sell for his proposed
reorganization of the material. Having been forced to teach out of books not of my choosing on several occasions, I
had found that a “bad” textbook did not prevent me from teaching a good course. I therefore hesitated to believe that
a “good” textbook would affect my teaching.
I had to admit, however, that not all was copacetic in the organic classroom. When my department hired another
organic chemist, I handed over second-semester organic to him with relief. I had consistently had a “crisis of faith”
in the midst of the second-semester course, struggling to get students to recognize the similarity between reactions in
separate chapters, wondering about the relevance of several topics, and grappling with the content in the sections
treating biological molecules. Toward the end of the second semester, I found that the course simply was not
enjoyable to teach. Consequently, I suspected that a better way to present the material to students had to exist.
Joel’s arguments for a book structured around mechanism types, as opposed to functional groups, came with two
types of evidence. First, Joel had done quantitative studies that supported his proposals. Second, he had credibility as
a teacher who actively considered students’ needs. During our first meeting, as well as the many discussions we had
later, I found Joel’s insights as an instructor consistent with my own, to the point that when his position challenged
mine, I felt I had to seriously consider his comments.
Fortunately, Joel and I met at a good time. One of my professional goals is to avoid becoming a fossilized professor.
I wanted to shake things up and was willing to make a change. The organic class was ripe for a pedagogical
revolution.
The initial draft of Joel’s book was so different from anything I had seen that its sheer novelty fascinated me, and I
was eager to try it. I suggested that I class-test the book and offer feedback. The first year’s trial was bumpy for
several reasons. By the second semester, though, his pedagogical revolution had clearly changed how my students
looked at organic chemistry—and in a good way.
What were those changes? For one thing, the experience revealed that several of my assumptions about the course
had been false. For example, I would have denied with my dying breath that I had expected my students to
memorize organic chemistry. Yet that first year, experiences I had with students showed that, in some ways, I
clearly had expected them to rely on memorization.
For all of us, students and instructor, the organization of the material led to a better experience. In the second
semester, the progression from anions to cations and then free radicals created a semester that started with
challenging, but doable, material, and concluded with material that students mastered readily. Each chapter’s focus
on reactions that were similar, without the “noise” from topics such as nomenclature and spectroscopy, was a major
improvement.
Finally, students asked me the best questions I had ever encountered. Those were questions that I had never heard
from other students, questions that reflected a strong understanding of organic chemistry—and questions that
frequently stumped me. I often admitted, “I’ll have to get back to you on that one.”
As teachers, we often discuss how students construct their learning from their experiences. What we discuss less
often is that we construct our teaching from our experiences. Our goal in writing this ’s Guide is to
improve your experience when you begin your own pedagogical revolution.
Steve Pruett
Jefferson Community and Technical College

(!3;2$)&&%1%.3!"/43
Several features set Organic Chemistry: Principles and Mechanisms apart from traditional chemistry texts.
%$ $
Yes, a simple review of the table of contents will tell you that. No, we cannot ignore the elephant in the room. That
significant difference elicits strong and, often, emotional responses from people who examine the book. (“Gasp! But
we’ve always taught organic chemistry by functional groups!”)
# $ $
Although all organic chemistry textbooks emphasize kinetics and thermodynamics in the context of substitution and
elimination reactions, those topics often fade into the background in later chapters. This textbook consistently
discusses the reversibility or irreversibility of reaction steps, using bond energies and charge stability as the basis for
qualitative evaluation. Those deceptively easy concepts do help students understand what occurs in reactions.
& !!" $ '
Chapter 7 introduces the elementary steps that students will see in practically all mechanisms in later chapters. To
our knowledge, this chapter is unique to this book. The bad news is that you must incorporate it into the first-
semester material, and it may seem to weight the division of material toward the first semester. The good news, and
the reward for spending time with this chapter, is that it liberates you to discuss any organic mechanism with your
students. Once they recognize the common elementary steps, most organic mechanisms are accessible to them.
$
In many sections, the author has supplied simplifications that allow students to remove “noise” from the signal we
are trying to send. For example, in describing organolithium, Grignard, and hydride reagents, he relegates the
cations and aluminum and boron to the role of spectators, and shows simple carbanions and hydride anions as the
reactants. That simplification allows students to see and understand the more reactive portion of the reagents and
ignore ions and atoms that, at this level of presentation, can be readily omitted.
Another thoughtful treatment of pedagogical issues includes segregation of nomenclature. All the nomenclature
topics are contained in five interchapters (Interchapters A, B, C, E, and F) spread throughout the textbook. That
approach allows you to incorporate the material when and how you choose. For example, some instructors cover all
the nomenclature material in the first semester—a benefit to those students who take only one semester of organic.
Other instructors require students to basically learn nomenclature on their own, without devoting classroom time to
it. The material is essentially paradigmatic, and students learn it easily. With this next edition of Joel’s textbook,
nomenclature is spread out into more interchapters, making it easier for students to learn it on their own.
Cliff and Steve initially opposed that approach to nomenclature. Their rationale was that, as in a language class,
students should be exposed to concepts one at a time; also, nomenclature was an “easy” part of each chapter.
However, learning nomenclature is analogous to learning to conjugate verbs, and students simply need examples and
exercises. There really is not anything to teach, except rules. They found that having students master that on their
own, and testing them on quizzes or on a single exam at the end of the course, was at least as effective as the
traditional approach. The organization of the nomenclature, based on functional group and similarities in rules,
makes learning organic chemistry nomenclature easy for students. Moreover, we are happy not to have to spend time
on the topic.
A further example is the segregation of biological topics at the ends of certain chapters. Textbooks traditionally
include chapters on carbohydrates and proteins, and often chapters on nucleic acids and lipids. However, Joel has
collected informal data indicating that most instructors do not get to those chapters in a normal course. Cliff is one
such instructor. Though he has a passion for carbohydrates and synthesizing carbohydrate-based materials, enough
time is never available to effectively incorporate that into undergraduate organic chemistry. In addition, in our
experience, much of the material in such chapters does not belong in an organic chemistry course. For example, in
my former textbooks, much of the protein chemistry and nucleic acid chemistry restated what students learn in
biology courses.

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