STUDENT SOLUTIONS MANUAL
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
Preface
What enters your mind when you hear the words “organic chemistry?” Some of you may
think, “the chemistry of life,” or “the chemistry of carbon.” Other responses might include “pre-
med,” “pressure,” “difficult,” or “memorization.” Although formally the study of the
compounds of carbon, the discipline of organic chemistry encompasses many skills that are
common to other areas of study. Organic chemistry is as much a liberal art as a science, and
mastery of the concepts and techniques of organic chemistry can lead to improved competence
in other fields.
As you work on the problems that accompany the text, you will bring to the task many
problem-solving techniques. For example, planning an organic synthesis requires the skills of a
chess player; you must plan your moves while looking several steps ahead, and you must keep
your plan flexible. Structure-determination problems are like detective problems, in which
many clues must be assembled to yield the most likely solution. Naming organic compounds is
similar to the systematic naming of biological specimens; in both cases, a set of rules must be
learned and then applied to the specimen or compound under study.
The problems in the text fall into two categories: drill and complex. Drill problems, which
appear throughout the text and at the end of each chapter, test your knowledge of one fact or
technique at a time. You may need to rely on memorization to solve these problems, which you
should work on first. More complicated problems require you to recall facts from several parts
of the text and then use one or more of the problem-solving techniques mentioned above. As
each major type of problem—synthesis, nomenclature, or structure determination—is
introduced in the text, a solution is extensively worked out in this Student Solutions Manual.
Here are several suggestions that may help you with problem solving:
1. The text is organized into chapters that describe individual functional groups. As
you study each functional group, make sure that you understand the structure and
reactivity of that group. In case your memory of a specific reaction fails you, you
can rely on your general knowledge of functional groups for help.
2. Use molecular models. It is difficult to visualize the three-dimensional structure of
an organic molecule when looking at a two-dimensional drawing. Models will help
you to appreciate the structural aspects of organic chemistry and are indispensable
tools for understanding stereochemistry.
3. Every effort has been made to make this Student Solutions Manual as clear,
attractive, and error-free as possible. Nevertheless, you should use the Student
Solutions Manual in moderation. The principal use of this book should be to
check answers to problems you have already worked out. The Student Solutions
Manual should not be used as a substitute for effort; at times, struggling with a
problem is the only way to teach yourself.
I have tried to include many types of study aids in this Student Solutions Manual.
Nevertheless, this book can only serve as an adjunct to the larger and more complete
textbook. If Organic Chemistry: A Tenth Edition is the guidebook to your study of organic
chemistry, then the Student Solutions Manual is the roadmap that shows you how to find
what you need.
10/27/2023 2
,OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
The Student Solutions Manual to accompany Organic Chemistry: A Tenth Edition, for
the first time, is being published by OpenStax. I am pleased that OpenStax will make this
resource freely available to you in honor of my late son, Peter McMurry.
Susan McMurry
Acknowledgments
Bryant Gilbert, Zane State College
Kjir Hendrickson, Arizona State University
Ekaterina Kadnikova, Hamline University
Ellen Moore, University of Missouri
Ike Shibley, Penn State Berks
3 10/27/2023
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
Chapter 1 – Structure and Bonding
Solutions to Problems
1.1 (a) To find the ground-state electron configuration of an element, first locate its atomic
number. For oxygen, the atomic number is 8; oxygen thus has 8 protons and 8
electrons. Next, assign the electrons to the proper energy levels, starting with the
lowest level. Fill each level completely before assigning electrons to a higher energy
level.
Notice that the 2p electrons are in different orbitals. According to Hund’s rule, we
must place one electron into each orbital of the same energy level until all orbitals are
half-filled.
Remember that only two electrons can occupy the same orbital, and that they must be
of opposite spin.
A different way to represent the ground-state electron configuration is to simply write
down the occupied orbitals and to indicate the number of electrons in each orbital.
For example, the electron configuration for oxygen is 1s2 2s2 2p4.
(b) Nitrogen, with an atomic number of 7, has 7 electrons. Assign these to energy
levels.
The more concise way to represent ground-state electron configuration for nitrogen:
1s2 2s2 2p3
(c) Sulfur has 16 electrons.
1s2 2s2 2p6 3s2 3p4
1/8/2024 4
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
Preface
What enters your mind when you hear the words “organic chemistry?” Some of you may
think, “the chemistry of life,” or “the chemistry of carbon.” Other responses might include “pre-
med,” “pressure,” “difficult,” or “memorization.” Although formally the study of the
compounds of carbon, the discipline of organic chemistry encompasses many skills that are
common to other areas of study. Organic chemistry is as much a liberal art as a science, and
mastery of the concepts and techniques of organic chemistry can lead to improved competence
in other fields.
As you work on the problems that accompany the text, you will bring to the task many
problem-solving techniques. For example, planning an organic synthesis requires the skills of a
chess player; you must plan your moves while looking several steps ahead, and you must keep
your plan flexible. Structure-determination problems are like detective problems, in which
many clues must be assembled to yield the most likely solution. Naming organic compounds is
similar to the systematic naming of biological specimens; in both cases, a set of rules must be
learned and then applied to the specimen or compound under study.
The problems in the text fall into two categories: drill and complex. Drill problems, which
appear throughout the text and at the end of each chapter, test your knowledge of one fact or
technique at a time. You may need to rely on memorization to solve these problems, which you
should work on first. More complicated problems require you to recall facts from several parts
of the text and then use one or more of the problem-solving techniques mentioned above. As
each major type of problem—synthesis, nomenclature, or structure determination—is
introduced in the text, a solution is extensively worked out in this Student Solutions Manual.
Here are several suggestions that may help you with problem solving:
1. The text is organized into chapters that describe individual functional groups. As
you study each functional group, make sure that you understand the structure and
reactivity of that group. In case your memory of a specific reaction fails you, you
can rely on your general knowledge of functional groups for help.
2. Use molecular models. It is difficult to visualize the three-dimensional structure of
an organic molecule when looking at a two-dimensional drawing. Models will help
you to appreciate the structural aspects of organic chemistry and are indispensable
tools for understanding stereochemistry.
3. Every effort has been made to make this Student Solutions Manual as clear,
attractive, and error-free as possible. Nevertheless, you should use the Student
Solutions Manual in moderation. The principal use of this book should be to
check answers to problems you have already worked out. The Student Solutions
Manual should not be used as a substitute for effort; at times, struggling with a
problem is the only way to teach yourself.
I have tried to include many types of study aids in this Student Solutions Manual.
Nevertheless, this book can only serve as an adjunct to the larger and more complete
textbook. If Organic Chemistry: A Tenth Edition is the guidebook to your study of organic
chemistry, then the Student Solutions Manual is the roadmap that shows you how to find
what you need.
10/27/2023 2
,OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
The Student Solutions Manual to accompany Organic Chemistry: A Tenth Edition, for
the first time, is being published by OpenStax. I am pleased that OpenStax will make this
resource freely available to you in honor of my late son, Peter McMurry.
Susan McMurry
Acknowledgments
Bryant Gilbert, Zane State College
Kjir Hendrickson, Arizona State University
Ekaterina Kadnikova, Hamline University
Ellen Moore, University of Missouri
Ike Shibley, Penn State Berks
3 10/27/2023
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual ch 1- 16
Chapter 1 – Structure and Bonding
Solutions to Problems
1.1 (a) To find the ground-state electron configuration of an element, first locate its atomic
number. For oxygen, the atomic number is 8; oxygen thus has 8 protons and 8
electrons. Next, assign the electrons to the proper energy levels, starting with the
lowest level. Fill each level completely before assigning electrons to a higher energy
level.
Notice that the 2p electrons are in different orbitals. According to Hund’s rule, we
must place one electron into each orbital of the same energy level until all orbitals are
half-filled.
Remember that only two electrons can occupy the same orbital, and that they must be
of opposite spin.
A different way to represent the ground-state electron configuration is to simply write
down the occupied orbitals and to indicate the number of electrons in each orbital.
For example, the electron configuration for oxygen is 1s2 2s2 2p4.
(b) Nitrogen, with an atomic number of 7, has 7 electrons. Assign these to energy
levels.
The more concise way to represent ground-state electron configuration for nitrogen:
1s2 2s2 2p3
(c) Sulfur has 16 electrons.
1s2 2s2 2p6 3s2 3p4
1/8/2024 4
