Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review Organic Chemistry Review
® MCAT Organic Chemistry Review Edited by Alexander Stone Macnow, MD Table of Contents MCAT® Organic Chemistry Review Cover Title Page Table of Contents The Kaplan MCAT Review Team About Scientific American About the MCAT How This Book Was Created Using This Book Chapter 1: Nomenclature Nomenclature Introduction 1.1 IUPAC Naming Conventions 1.2 Hydrocarbons and Alcohols 1.3 Aldehydes and Ketones 1.4 Carboxylic Acids and Derivatives 1.5 Summary of Functional Groups Conclusion Concept Summary 10 Answers to Concept Checks 11 Shared Concepts 12 Practice Questions 13 Answers and Explanations Chapter 2: Isomers Isomers Introduction 2.1 Structural Isomers 2.2 Stereoisomers 2.3 Relative and Absolute Configurations Conclusion Concept Summary Answers to Concept Checks Equations to Remember 10 Shared Concepts 11 Practice Questions 12 Answers and Explanations Chapter 3: Bonding Bonding Introduction 3.1 Atomic Orbitals and Quantum Numbers 3.2 Molecular Orbitals 3.3 Hybridization Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations Chapter 4: Analyzing Organic Reactions Analyzing Organic Reactions Introduction 4.1 Acids and Bases 4.2 Nucleophiles, Electrophiles, and Leaving Groups 4.3 Oxidation–Reduction Reactions 4.4 Chemoselectivity 4.5 Steps to Problem-Solving Conclusion Concept Summary 10 Answers to Concept Checks 11 Equations to Remember 12 Shared Concepts 13 Practice Questions 14 Answers and Explanations Chapter 5: Alcohols Alcohols Introduction 5.1 Description and Properties 5.2 Reactions of Alcohols 5.3 Reactions of Phenols Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations Chapter 6: Aldehydes and Ketones I: Electrophilicity and Oxidation—Reduction Aldehydes and Ketones I: Electrophilicity and Oxidation— Reduction Introduction 6.1 Description and Properties 6.2 Nucleophilic Addition Reactions 6.3 Oxidation–Reduction Reactions Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations Chapter 7: Aldehyde and Ketones II: Enolates Aldehyde and Ketones II: Enolates Introduction 7.1 General Principles 7.2 Enolate Chemistry 7.3 Aldol Condensation Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations Chapter 8: Carboxylic Acids Carboxylic Acids Introduction 8.1 Description and Properties 8.2 Reactions of Carboxylic Acids Conclusion Concept Summary Answers to Concept Checks Shared Concepts Practice Questions 10 Answers and Explanations 10 Chapter 9: Carboxylic Acid Derivatives Carboxylic Acid Derivatives Introduction 9.1 Amides, Esters, and Anhydrides 9.2 Reactivity Principles 9.3 Nucleophilic Acyl Substitution Reactions Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations 11 Chapter 10: Nitrogen- and Phosphorus-Containing Compounds Nitrogen- and Phosphorus-Containing Compounds Introduction 10.1 Amino Acids, Peptides, and Proteins 10.2 Synthesis of α-Amino Acids 10.3 Phosphorus-Containing Compounds Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations 12 Chapter 11: Spectroscopy Spectroscopy Introduction 11.1 Infrared Spectroscopy 11.2 Ultraviolet Spectroscopy 11.3 Nuclear Magnetic Resonance Spectroscopy Conclusion Concept Summary Answers to Concept Checks Shared Concepts 10 Practice Questions 11 Answers and Explanations 13 Chapter 12: Separations and Purifications Separations and Purifications Introduction 12.1 Solubility-Based Methods 12.2 Distillation 12.3 Chromatography Conclusion Concept Summary Answers to Concept Checks Equations to Remember 10 Shared Concepts 11 Practice Questions 12 Answers and Explanations 14 About This Book Copyright Information Glossary Index Art Credits Periodic Table of the Elements 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 Polar solvents, 87, 269, 277, 284, 298 Polypeptides, 227, 236, 298 Positively charged (basic) amino acids, 227, 236 Preparative thin-layer chromatography, 277, 298 Principal quantum number, 62, 71, 298 Proline, 227, 236 Propanal See Propionaldehyde Propionaldehyde, 11, 19, 138 Proteins, 65, 112, 225, 227, 228, 236, 279 Protonation, 97, 298 Proton chemical shift ranges, 255t Proton NMR 1,1-dibromo-2-chloroethane, 254f 1,1-dibromo-2,2-dichloroethane, 254f dichloromethyl methyl ether, 253f Proton NMR (1H–NMR), 252–256, 259 Pyridinium chlorochromate, 91, 100, 105, 119, 126, 139, 147 Pyridinium chlorochromate (PCC): oxidation of a primary alcohol to an aldehyde, 119f Pyrophosphate, 233, 234, 237, 298 Pyrophosphate anion, 233f Pyruvate dehydrogenase, 188 Q Quantum numbers, 61–62, 71 Quinone, oxidation of phenol to, 122f Quinones, 122–124, 125, 127, 296, 298, 300 R (R ) and (S ) nomenclature, 44 – 46, 46, 50 (R )/(S ) designation, drawing a circle to determine 46f Racemic mixtures, 41, 43, 49, 89, 104, 230, 232, 298 Reactivity principles, 206–208, 214–215 Recrystallization, 271, 283 Reducing agents, 92–94, 97, 105, 187, 191, 207 Reducing agents, common, reduction reactions and, 93f Reduction aldehydes and ketones, 92, 106, 145, 147 amides, 92, 105 carboxylic acids, 105, 187, 191 esters, 105 See also Oxidation–reduction (redox) reactions Reduction reactions carboxylic acid to primary alcohol, 187f common: reducing agents and 93f ketones, 145f Relative configuration, 43–46, 50, 298 Residue, 271, 283 Resonance, 68–69, 72, 118, 228, 236, 298 amides, 185f peptide bonds, 228f Resonance forms: carbonate, 68f Retardation factor, 277, 284, 286, 298 Retro-aldol reaction, 166f Retro-aldol reactions, 166, 169, 298 Reverse-phase chromatography, 277, 284, 298 Ring strain, 36, 208, 215, 298 Rotary evaporators, 271 S Saponification, 188–189, 190, 192, 203, 214, 298 Separations and purifications, 269–284 See also Chromatography; Distillation; Extraction; Filtration; Recrystallization Separatory funnel, 270f Separatory funnels, 270f–271, 283, 299 Shielding, 253, 299 Sigma (σ) bonds, 64–65, 71, 299 Simple distillation, 272, 283, 299 Size-exclusion chromatography, 279, 284, 299 SN1 reactions, 88–89, 95, 104 SN2 reactions, 88, 89, 95, 104, 231 Soap micelle, 189f Soaps, 179, 188–189, 192, 203–204, 214, 298 Sodium borohydride, 106, 145, 187, 191 Solvent effects, 86–87 Specific rotation, 41, 42, 299 Spectroscopy, 247–259, 299 Spin quantum number, 62, 71, 299 Spin-spin coupling, 254, 259 Splitting patterns, 254 Spotting, 276, 299 Staggered conformations, 35, 49 Stationary phase, 275–280, 283–284, 299 Stereoisomers, 34–38, 49–50, 299 Stereoselectivity, 98, 99, 105, 107 Steric hindrance, 86, 95, 160, 206–207, 214, 299 Steric protection, 95, 299 Steric strain See Nonbonded strain Straight-chain conformational isomers: stability, 35f Straight-chain conformations, 34–35 Strecker synthesis, 229f, 229–230, 230f, 232, 235, 237 Structural (constitutional) isomers: C6H14, 33f Structural isomers, 31–33, 49, 299 Substituents, common alternative alkyl substituents, 6f normal alkyl substituents, 5f Substituents, multiple, rings with: nomenclature, 38f Substituents: naming steps, 4–5 T Tautomerization, 143, 161f, 161–162, 163, 163f, 188 Tautomers, 161, 163, 168, 299 Tetramethylsilane, 252, 254, 259, 299 Thermodynamic enolate, 162–163, 168 Thermodynamic enolates, 163f Thin-layer chromatography (TLC), 275, 275–276, 277f, 278, 284, 299 Torsional strain, 36, 49, 98, 208, 215, 298, 299 Tosylates, 89, 118, 120, 126, 299 Tosylate: structure, 120f Totally eclipsed conformations, 35, 49 Transesterification, 211, 211f, 215, 300 Transmittance (IR spectra), 249, 258 Triacylglycerols, 203–204, 214, 300 Triacylglycerol: saponification, 204f Triplets, 254, 255, 259, 300 U Ubiquinol 124f Ubiquinol, 123–124, 127 Ubiquinone (coenzyme Q) 124f Ubiquinones, 123–124, 128, 300 Ultraviolet (UV) spectroscopy, 250–251, 257, 258, 300 Unimolecular nucleophilic substitution (SN1) reactions, 88f 88–89, 104 Upfield, 254, 259, 300 V Vacuum distillation, 273, 273f, 283, 300 Vacuum filtration, 271, 285 Van der Waals forces, 36, 128, 271 Vapor-phase chromatography (VPC), 280 Vicinal diols, 10, 19, 300 Vitamin K1 See Phylloquinone Vitamin K1 and K2, 122, 127 W Washes, 271, 283, 300 Water: pKa value, 83t Wavenumbers, 248–249, 258, 300 Z Zwitterions, 226–227, 227f, 236, 300 Art Credits Chapter 2 Cover—Image credited to Vladyslav Starozhylov From Shutterstock Chapter 3 Cover—Image credited to FikMik From Shutterstock Figure 3.1—Image credited to User: Sven From Wikimedia Commons Copyright © 2006 Used under licenses: CC-BY-SA-3.0 / CC-BY-SA-2.52.0-1.0 / GFDL Chapter 4 Cover—Image credited to Andrea Danti From Shutterstock Chapter 5 Cover—Image credited to Wollertz From Shutterstock Chapter 7 Cover—Image credited to Dusan Jankovic From Shutterstock Chapter 8 Cover—Image credited to Quayside From Shutterstock Chapter 9 Cover—Image credited to Mike Laptev From Shutterstock Chapter 11 Cover—Image credited to Oliver Sved From Shutterstock Figure 11.3 (graphs)—Image credited to Lucy Reading-Ikkanda From The Incredible Shrinking Scanner by Bernhard Blümich Copyright © 2008 by Scientific American, Inc All rights reserved Figure 11.3 (MRI machine)—Image credited to George Retseck From The Incredible Shrinking Scanner by Bernhard Blümich Copyright © 2008 by Scientific American, Inc All rights reserved Figure 11.3 (MRI image)—Image credited to Mehau Kulyk SPL / Photo Researchers, Inc From The Incredible Shrinking Scanner by Bernhard Blümich Copyright © 2008 by Scientific American, Inc All rights reserved Chapter 12 Cover—Image credited to luchschen From Shutterstock Periodic Table of the Elements ...® MCAT Organic Chemistry Review Edited by Alexander Stone Macnow, MD Table of Contents MCAT® Organic Chemistry Review Cover Title Page Table of Contents The Kaplan MCAT Review Team About Scientific American... 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)... 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