STUDY GUIDE
, OpenStax Organic Chemistry: A Tenth Edition Study Guide
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.
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. Look through the appendices at the end of the Study Guide. Some of these
appendices contain tables that may help you in working problems; others present
information related to the history of organic chemistry.
While the Study Guide is written to accompany Organic Chemistry, it also contains several
unique features. Each chapter of the Study Guide begins with an outline of the text that can be
used for a concise review of the text material and can also serve as a reference. After every few
chapters a Review Unit is included. In most cases, the chapters covered in the Review Units are
related to each other, and the units are planned to appear at approximately the place in the
textbook where a test might be given. Each unit lists the vocabulary for the chapters covered,
the skills needed to solve problems, and several important points that might need reinforcing or
that restate material in the text from a slightly different point of view. Finally, the small self-test
that has been included allows you to test yourself on the material from more than one chapter.
I have tried to include many types of study aids in this Study Guide. Nevertheless, this book can
only serve as an adjunct to the larger and more complete textbook. In addition, please note that
a companion to this Study Guide, the Student Solutions Manual, contains solutions to the
problems found in Organic Chemistry: A Tenth Edition. I am pleased that this is the first time
that these are published by OpenStax and available to you for free in honor of my late son, Peter
McMurry.
Susan McMurry
Acknowledgments
Bryant Gilbert, Zane State College
Kjir Hendrickson, Arizona State University
Ike Shibley, Penn State Berks
10/27/2023 2
,OpenStax Organic Chemistry: A Tenth Edition Study Guide
Table of Contents
Chapter 1: Structure and Bonding 5
Chapter 2: Polar Covalent Bonds; Acids and Bases 9
Review Unit 1 12
Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry 15
Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry 19
Chapter 5: Stereochemistry at Tetrahedral Centers 22
Review Unit 2 25
Chapter 6: An Overview of Organic Reactions 29
Chapter 7: Alkenes: Structure and Reactivity 32
Chapter 8: Alkenes: Reactions and Synthesis 35
Review Unit 3 38
Chapter 9: Alkynes: An Introduction to Organic Synthesis 43
Chapter 10: Organohalides 45
Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 48
Review Unit 4 53
Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy 56
Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy 60
Review Unit 5 65
Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy 70
Chapter 15: Benzene and Aromaticity 73
Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution 77
Review Unit 6 81
Chapter 17: Alcohols and Phenols 86
Chapter 18: Ethers and Epoxides; Thiols and Sulfides 90
Preview of Carbonyl Chemistry 93
Review Unit 7 94
Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions 97
Chapter 20: Carboxylic Acids and Nitriles 102
Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 105
Review Unit 8 110
3 10/27/2023
, OpenStax Organic Chemistry: A Tenth Edition Study Guide
Chapter 22: Carbonyl Alpha-Substitution Reactions 115
Chapter 23: Carbonyl Condensation Reactions 118
Chapter 24: Amines and Heterocycles 121
Review Unit 9 126
Chapter 25: Biomolecules: Carbohydrates 131
Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins 136
Review Unit 10 142
Chapter 27: Biomolecules: Lipids 147
Chapter 28: Biomolecules: Nucleic Acids 150
Chapter 29: The Organic Chemistry of Metabolic Pathways 154
Review Unit 11 160
Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions 165
Chapter 31: Synthetic Polymers 168
Review Unit 12 171
Appendices
Appendix A: Functional-Group Synthesis 175
Appendix B: Functional-Group Reactions 181
Appendix C: Reagents in Organic Chemistry 186
Appendix D: Name Reactions in Organic Chemistry 194
Appendix E: Abbreviations 202
Appendix F: Infrared Absorption Frequencies 206
Appendix G: Proton NMR Chemical Shifts 209
Appendix H: Nobel Prize Winners in Chemistry 210
Appendix I: Answers to Multiple Choice Questions in Review Units 1–12 222
10/27/2023 4
, OpenStax Organic Chemistry: A Tenth Edition Study Guide
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.
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. Look through the appendices at the end of the Study Guide. Some of these
appendices contain tables that may help you in working problems; others present
information related to the history of organic chemistry.
While the Study Guide is written to accompany Organic Chemistry, it also contains several
unique features. Each chapter of the Study Guide begins with an outline of the text that can be
used for a concise review of the text material and can also serve as a reference. After every few
chapters a Review Unit is included. In most cases, the chapters covered in the Review Units are
related to each other, and the units are planned to appear at approximately the place in the
textbook where a test might be given. Each unit lists the vocabulary for the chapters covered,
the skills needed to solve problems, and several important points that might need reinforcing or
that restate material in the text from a slightly different point of view. Finally, the small self-test
that has been included allows you to test yourself on the material from more than one chapter.
I have tried to include many types of study aids in this Study Guide. Nevertheless, this book can
only serve as an adjunct to the larger and more complete textbook. In addition, please note that
a companion to this Study Guide, the Student Solutions Manual, contains solutions to the
problems found in Organic Chemistry: A Tenth Edition. I am pleased that this is the first time
that these are published by OpenStax and available to you for free in honor of my late son, Peter
McMurry.
Susan McMurry
Acknowledgments
Bryant Gilbert, Zane State College
Kjir Hendrickson, Arizona State University
Ike Shibley, Penn State Berks
10/27/2023 2
,OpenStax Organic Chemistry: A Tenth Edition Study Guide
Table of Contents
Chapter 1: Structure and Bonding 5
Chapter 2: Polar Covalent Bonds; Acids and Bases 9
Review Unit 1 12
Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry 15
Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry 19
Chapter 5: Stereochemistry at Tetrahedral Centers 22
Review Unit 2 25
Chapter 6: An Overview of Organic Reactions 29
Chapter 7: Alkenes: Structure and Reactivity 32
Chapter 8: Alkenes: Reactions and Synthesis 35
Review Unit 3 38
Chapter 9: Alkynes: An Introduction to Organic Synthesis 43
Chapter 10: Organohalides 45
Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 48
Review Unit 4 53
Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy 56
Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy 60
Review Unit 5 65
Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy 70
Chapter 15: Benzene and Aromaticity 73
Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution 77
Review Unit 6 81
Chapter 17: Alcohols and Phenols 86
Chapter 18: Ethers and Epoxides; Thiols and Sulfides 90
Preview of Carbonyl Chemistry 93
Review Unit 7 94
Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions 97
Chapter 20: Carboxylic Acids and Nitriles 102
Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 105
Review Unit 8 110
3 10/27/2023
, OpenStax Organic Chemistry: A Tenth Edition Study Guide
Chapter 22: Carbonyl Alpha-Substitution Reactions 115
Chapter 23: Carbonyl Condensation Reactions 118
Chapter 24: Amines and Heterocycles 121
Review Unit 9 126
Chapter 25: Biomolecules: Carbohydrates 131
Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins 136
Review Unit 10 142
Chapter 27: Biomolecules: Lipids 147
Chapter 28: Biomolecules: Nucleic Acids 150
Chapter 29: The Organic Chemistry of Metabolic Pathways 154
Review Unit 11 160
Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions 165
Chapter 31: Synthetic Polymers 168
Review Unit 12 171
Appendices
Appendix A: Functional-Group Synthesis 175
Appendix B: Functional-Group Reactions 181
Appendix C: Reagents in Organic Chemistry 186
Appendix D: Name Reactions in Organic Chemistry 194
Appendix E: Abbreviations 202
Appendix F: Infrared Absorption Frequencies 206
Appendix G: Proton NMR Chemical Shifts 209
Appendix H: Nobel Prize Winners in Chemistry 210
Appendix I: Answers to Multiple Choice Questions in Review Units 1–12 222
10/27/2023 4
