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Tài liệu Organic Chemistry Review

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® 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).
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