®
MCAT Organic Chemistry
Review
Edited by Alexander Stone Macnow, MD
Table of Contents
1. MCAT® Organic Chemistry Review
1. Cover
1. Title Page
2. Table of Contents
3. The Kaplan MCAT Review Team
4. About Scientific American
5. About the MCAT
6. How This Book Was Created
7. Using This Book
2. Chapter 1: Nomenclature
1. Nomenclature
2. Introduction
3. 1.1 IUPAC Naming Conventions
4. 1.2 Hydrocarbons and Alcohols
5. 1.3 Aldehydes and Ketones
6. 1.4 Carboxylic Acids and Derivatives
7. 1.5 Summary of Functional Groups
8. Conclusion
9. Concept Summary
10. Answers to Concept Checks
11. Shared Concepts
12. Practice Questions
13. Answers and Explanations
3. Chapter 2: Isomers
1. Isomers
2. Introduction
3. 2.1 Structural Isomers
4. 2.2 Stereoisomers
5. 2.3 Relative and Absolute Configurations
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Equations to Remember
10. Shared Concepts
11. Practice Questions
12. Answers and Explanations
4. Chapter 3: Bonding
1. Bonding
2. Introduction
3. 3.1 Atomic Orbitals and Quantum Numbers
4. 3.2 Molecular Orbitals
5. 3.3 Hybridization
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
5. Chapter 4: Analyzing Organic Reactions
1. Analyzing Organic Reactions
2. Introduction
3. 4.1 Acids and Bases
4. 4.2 Nucleophiles, Electrophiles, and Leaving Groups
5. 4.3 Oxidation–Reduction Reactions
6. 4.4 Chemoselectivity
7. 4.5 Steps to Problem-Solving
8. Conclusion
9. Concept Summary
10. Answers to Concept Checks
11. Equations to Remember
12. Shared Concepts
13. Practice Questions
14. Answers and Explanations
6. Chapter 5: Alcohols
1. Alcohols
2. Introduction
3. 5.1 Description and Properties
4. 5.2 Reactions of Alcohols
5. 5.3 Reactions of Phenols
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
7. Chapter 6: Aldehydes and Ketones I: Electrophilicity and
Oxidation—Reduction
1. Aldehydes and Ketones I: Electrophilicity and Oxidation—
Reduction
2. Introduction
3. 6.1 Description and Properties
4. 6.2 Nucleophilic Addition Reactions
5. 6.3 Oxidation–Reduction Reactions
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
8. Chapter 7: Aldehyde and Ketones II: Enolates
1. Aldehyde and Ketones II: Enolates
2. Introduction
3. 7.1 General Principles
4. 7.2 Enolate Chemistry
5. 7.3 Aldol Condensation
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
9. Chapter 8: Carboxylic Acids
1. Carboxylic Acids
2. Introduction
3. 8.1 Description and Properties
4. 8.2 Reactions of Carboxylic Acids
5. Conclusion
6. Concept Summary
7. Answers to Concept Checks
8. Shared Concepts
9. Practice Questions
10. Answers and Explanations
10. Chapter 9: Carboxylic Acid Derivatives
1. Carboxylic Acid Derivatives
2. Introduction
3. 9.1 Amides, Esters, and Anhydrides
4. 9.2 Reactivity Principles
5. 9.3 Nucleophilic Acyl Substitution Reactions
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
11. Chapter 10: Nitrogen- and Phosphorus-Containing Compounds
1. Nitrogen- and Phosphorus-Containing Compounds
2. Introduction
3. 10.1 Amino Acids, Peptides, and Proteins
4. 10.2 Synthesis of α-Amino Acids
5. 10.3 Phosphorus-Containing Compounds
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
12. Chapter 11: Spectroscopy
1. Spectroscopy
2. Introduction
3. 11.1 Infrared Spectroscopy
4. 11.2 Ultraviolet Spectroscopy
5. 11.3 Nuclear Magnetic Resonance Spectroscopy
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Shared Concepts
10. Practice Questions
11. Answers and Explanations
13. Chapter 12: Separations and Purifications
1. Separations and Purifications
2. Introduction
3. 12.1 Solubility-Based Methods
4. 12.2 Distillation
5. 12.3 Chromatography
6. Conclusion
7. Concept Summary
8. Answers to Concept Checks
9. Equations to Remember
10. Shared Concepts
11. Practice Questions
12. Answers and Explanations
14. About This Book
1. Copyright Information
2. Glossary
3. Index
4. Art Credits
5. Periodic Table of the Elements
6. Special Offer for Kaplan Students
The Kaplan MCAT Review Team
Alexander Stone Macnow, MD
Editor-in-Chief
Kelly Kyker-Snowman, MS
Kaplan MCAT Faculty
MCAT faculty reviewers Elmar R. Aliyev; James Burns; Jonathan
Cornfield; Alisha Maureen Crowley; Nikolai Dorofeev, MD; Benjamin
Downer, MS; Colin Doyle; M. Dominic Eggert; Marilyn Engle; Eleni M.
Eren; Raef Ali Fadel; Tyra Hall-Pogar, PhD; Scott Huff; Samer T. Ismail;
Elizabeth A. Kudlaty; Ningfei Li; John P. Mahon; Matthew A. Meier;
Nainika Nanda; Caroline Nkemdilim Opene; Kaitlyn E. Prenger; Uneeb
Qureshi; Derek Rusnak, MA; Kristen L. Russell, ME; Bela G. Starkman,
PhD; Michael Paul Tomani, MS; Nicholas M. White; Kerranna
Williamson, MBA; Allison Ann Wilkes, MS; and Tony Yu
Thanks to Kim Bowers; Tim Eich; Samantha Fallon; Owen Farcy; Dan
Frey; Robin Garmise; Rita Garhaffner; Joanna Graham; Adam Grey;
Allison Harm; Beth Hoffberg; Aaron Lemon-Strauss; Keith Lubeley;
Diane McGarvey; Petros Minasi; John Polstein; Deeangelee PooranKublall, MD, MPH; Rochelle Rothstein, MD; Larry Rudman; Sylvia
Tidwell Scheuring; Carly Schnur; Karin Tucker; Lee Weiss; and the
countless others who made this project possible.
About Scientific American
Scientific American is at the heart of Nature Publishing Group’s consumer
media division, meeting the needs of the general public. Founded in 1845,
Scientific American is the longest continuously published magazine in the
United States and the leading authoritative publication for science in the
general media. In its history, 148 Nobel Prize scientists have contributed
240 articles to Scientific American, including Albert Einstein, Francis
Crick, Stanley Prusiner, and Richard Axel.
Together with scientificamerican.com and in translation in 14 languages
around the world, it reaches more than 5 million consumers and scientists.
Other titles include Scientific American Mind and Spektrum der
Wissenschaft in Germany. Scientific American won a 2011 National
Magazine Award for General Excellence.
About the MCAT
The structure of the four sections of the MCAT is shown below.
Chemical and Physical Foundations of Biological Systems
Time
Format
95 minutes
59 questions
10 passages
44 questions are passage-based, and 15 are discrete (stand-alone)
questions.
Score between 118 and 132
What It
Biochemistry: 25%
Tests
Biology: 5%
General Chemistry: 30%
Organic Chemistry: 15%
Physics: 25%
Critical Analysis and Reasoning Skills (CARS)
Time
Format
90 minutes
53 questions
9 passages
All questions are passage-based. There are no discrete (stand-alone)
questions.
Score between 118 and 132
What It
Disciplines:
Humanities: 50%
Tests
Social Sciences: 50%
Skills:
Foundations of Comprehension: 30%
Reasoning Within the Text: 30%
Reasoning Beyond the Text: 40%
Biological and Biochemical Foundations of Living Systems
Time
Format
95 minutes
59 questions
10 passages
44 questions are passage-based, and 15 are discrete (stand-alone)
questions.
Score between 118 and 132
What It
Biochemistry: 25%
Tests
Biology: 65%
General Chemistry: 5%
Organic Chemistry: 5%
Psychological, Social, and Biological Foundations of Behavior
Time
Format
95 minutes
59 questions
10 passages
44 questions are passage-based, and 15 are discrete (stand-alone)
questions.
Score between 118 and 132
What It
Biology: 5%
Tests
Psychology: 65%
Sociology: 30%
Total
Testing
375 minutes (6 hours, 15 minutes)
Time
Questions
230
Score
472 to 528
The MCAT also tests four Scientific Inquiry and Reasoning Skills (SIRS):
1. Knowledge of Scientific Concepts and Principles (35% of
questions)
2. Scientific Reasoning and Problem-Solving (45% of questions)
3. Reasoning About the Design and Execution of Research (10% of
questions)
4. Data-Based and Statistical Reasoning (10% of questions)
The MCAT is a computer-based test (CBT) and is offered at Prometric
centers during almost every month of the year. There are optional breaks
between each section, and there is a lunch break between the second and
third section of the exam.
Register online for the MCAT at www.aamc.org/mcat
.
For further questions, contact the MCAT team at the Association of
American Medical Colleges:
MCAT Resource Center
Association of American Medical Colleges
(202) 828-0690
www.aamc.org/mcat
[email protected]
How This Book Was Created
The Kaplan MCAT Review project began in November 2012 shortly after
the release of the Preview Guide for the MCAT 2015 Exam, 2nd edition.
Through thorough analysis by our staff psychometricians, we were able to
analyze the relative yield of the different topics on the MCAT, and we
began constructing tables of contents for the books of the Kaplan MCAT
Review series.
Writing of the books began in April 2013. A dedicated staff of 19 writers,
7 editors, and 32 proofreaders worked over 5000 combined hours to
produce these books. The format of the books was heavily influenced by
weekly meetings with Kaplan’s learning-science team.
These books were submitted for publication in July 2014. For any
updates after this date, please visit www.kaplanmcat.com .
The information presented in these books covers everything listed on the
official MCAT content lists—nothing more, nothing less. Every topic in
these lists is covered in the same level of detail as is common to the
undergraduate and postbaccalaureate classes that are considered
prerequisites for the MCAT. Note that your premedical classes may cover
topics not discussed in these books, or they may go into more depth than
these books do. Additional exposure to science content is never a bad
thing, but recognize that all of the content knowledge you are expected to
have walking in on Test Day is covered in these books.
If you have any questions about the content presented here, email
[email protected] . For other questions not related to
content, email
[email protected] .
Each book has been vetted through at least six rounds of review. To that
end, the information presented is these books is true and accurate to the
best of our knowledge. Still, your feedback helps us improve our prep
materials. Please notify us of any inaccuracies or errors in the books by
sending an email to
[email protected] .
Using This Book
Kaplan MCAT Organic Chemistry Review, along with the other six books
in the Kaplan MCAT Review series, brings the Kaplan classroom
experience to you—right in your home, at your convenience. This book
offers the same Kaplan content review, strategies, and practice that make
Kaplan the #1 choice for MCAT prep. After all, twice as many doctors
prepared with Kaplan for the MCAT than with any other course.
This book is designed to help you review the organic chemistry topics
covered on the MCAT. Please understand that content review—no matter
how thorough—is not sufficient preparation for the MCAT! The MCAT
tests not only your science knowledge but also your critical reading,
reasoning, and problem-solving skills. Do not assume that simply
memorizing the contents of this book will earn you high scores on Test
Day; to maximize your scores, you must also improve your reading and
test-taking skills through MCAT-style questions and practice tests.
MCAT CONCEPT CHECKS
At the end of each section, you’ll find a few open-ended questions that you
can use to assess your mastery of the material. These MCAT Concept
Checks were introduced after multiple conversations with Kaplan’s
learning-science team. Research has demonstrated repeatedly that
introspection and self-analysis improve mastery, retention, and recall of
material. Complete these MCAT Concept Checks to ensure that you’ve got
the key points from each section before moving on!
PRACTICE QUESTIONS
At the end of each chapter, you’ll find 15 MCAT-style practice questions.
These are designed to help you assess your understanding of the chapter
you just read. Most of these questions focus on the first of the Scientific
Inquiry and Reasoning Skills (Knowledge of Scientific Concepts and
Principles), although there are occasional questions that fall into the
second or fourth SIRS (Scientific Reasoning and Problem-Solving, and
Data-Based and Statistical Reasoning, respectively).