Editorial Robert Franek, Senior VP, Publisher Casey Cornelius, VP Content Development Mary Beth Garrick, Director of Production Selena Coppock, Managing Editor Calvin Cato, Editor Colleen Day, Editor Aaron Riccio, Editor Meave Shelton, Editor Orion McBean, Editorial Assistant Random House Publishing Team Tom Russell, Publisher Alison Stoltzfus, Publishing Manager Melinda Ackell, Associate Managing Editor Ellen Reed, Production Manager Kristin Lindner, Production Supervisor Andrea Lau, Designer The Princeton Review 24 Prime Parkway, Suite 201 Natick, MA 01760 E-mail: [email protected] Copyright © 2014 by TPR Education IP Holdings, LLC. All Rights Reserved. Cover art © Ikon Images/Alamy Published in the United States by Penguin Random House LLC, New York, and in Canada by Random House of Canada, a division of Penguin Random House Ltd., Toronto. The Princeton Review is not affiliated with Princeton University. The MCAT is a registered trademark of the Association of American Medical Colleges, which The MCAT is a registered trademark of the Association of American Medical Colleges, which does not sponsor or endorse this product. Terms of Service: The Princeton Review Online Companion Tools (“Student Tools”) for the Cracking book series and MCAT Review Series are available for only the two most recent editions of that book. Student Tools may be activated only once per eligible book purchased. Activation of Student Tools more than once per book is in direct violation of these Terms of Service and may result in discontinuation of access to Student Tools Services. eBook ISBN: 978-1-10188242-9 Trade Paperback ISBN: 978-0-8041-2505-5 Editor: Calvin Cato Production Editor: Harmony Quiroz Production Artist: Deborah A. Silvestrini v3.1 CONTRIBUTORS Peter J. Alaimo, Ph.D. Senior Author TPR MCAT O-Chem Development Team: Bethany Blackwell, M.S., Senior Editor, Lead Developer William Ewing, Ph.D. Brandon Kelley, Ph.D. Edited for Production by: Judene Wright, M.S., M.A.Ed. National Content Director, MCAT Program, The Princeton Review The TPR MCAT O-Chem Team and Judene would like to thank the following people for their contributions to this book: Farhad Aziz, B.S., Kristen Brunson, Ph.D., Brian Butts, B.S., B.A., Douglas S. Daniels, Ph.D., Amanda Edward, H.BSc, H.BEd, Carlos Guzman, Adam Johnson, Omair Adil Khan, Stefan Loren, Ph.D., Joey Mancuso, D.O., M.S., Janet Marshall, Ph.D., Douglas K. McLemore, B.S., Katherine Miller, B.A., Tenaya Newkirk, Ph.D., Jason Osman, M.S., Daniel J. Pallin, M.D., Tyler Peikes, Chris Rabbat, Ph.D., Steven Rines, Ph.D., Jayson Sack, M.D., M.S., Karen Salazar, Ph.D., Sina Shahbaz, B.S., Christopher Volpe, Ph.D. In addition, The Princeton Review would like to thank Calvin Cato, Harmony Quiroz, and Deborah Silvestrini, for their hard work on the production of this book. MCAT ORGANIC CHEMISTRY REVIEW CONTENTS Cover Title Page Copyright …So Much More Online! CHAPTER 1: MCAT 2015 BASICS CHAPTER 2: ORGANIC CHEMISTRY STRATEGY FOR THE MCAT 2.1 Science Sections Overview 2.2 General Science Passage Types 2.3 General Science Question Types 2.4 Organic Chemistry on the MCAT 2.5 Tackling an Organic Chemistry Passage 2.6 Tackling the Questions CHAPTER 3: ORGANIC CHEMISTRY FUNDAMENTALS 3.1 Background and Introduction 3.2 Abbreviated Line Structures 3.3 Nomenclature of Alkanes 3.4 Nomenclature of Haloalkanes 3.5 Nomenclature of Alcohols CHAPTER 4: STRUCTURE AND STABILITY 4.1 The Organic Chemist’s Toolbox 4.2 Isomerism Chapter 4 Summary Chapter 4 Freestanding Practice Questions Chapter 4 Practice Passage CHAPTER 5: LAB TECHNIQUES: SEPARATIONS AND SPECTROSCOPY 5.1 Separations 5.2 Spectroscopy Chapter 5 Summary Chapter 5 Freestanding Practice Questions Chapter 5 Practice Passage CHAPTER 6: CARBONYL CHEMISTRY 6.1 Aldehydes and Ketones 6.2 Carboxylic Acids 6.3 Carboxylic Acid Derivatives Chapter 6 Summary Chapter 6 Freestanding Practice Questions Chapter 6 Practice Passage CHAPTER 7: BIOLOGICALLY IMPORTANT MOLECULES 7.1 Amino Acids 7.2 Proteins 7.3 Carbohydrates 7.4 Lipids 7.5 Nucleic Acids Chapter 7 Summary Chapter 7 Freestanding Practice Questions Chapter 7 Practice Passage ORGANIC CHEMISTRY GLOSSARY SUMMARY OF REACTIONS Double click on the image to enlarge Chapter 1 MCAT 2015 Basics