{"product_id":"experimental-organic-chemistry-9780471282501","title":"Experimental Organic Chemistry","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003eThis cutting-edge lab manual takes a multiscale approach, presenting both micro, semi-micro, and macroscale techniques. The manual is easy to navigate with all relevant techniques found as they are needed. Cutting-edge subjects such as HPLC, bioorganic chemistry, multistep synthesis, and more are presented in a clear and engaging fashion.\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTrade Review\u003c\/b\u003e\u003cbr\u003e\"As a teacher, I feel that this is one of the best books of its type...\" (Education in Chemistry, January 2001)\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003e\u003cb\u003eSection 1 The Basics 1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 1 Laboratory Safety 3\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e1.1 General Safety Guidelines 3\u003c\/p\u003e \u003cp\u003e1.2 Chemical Toxicity 6\u003c\/p\u003e \u003cp\u003e1.3 Dealing with Chemicals and Waste Disposal 7\u003c\/p\u003e \u003cp\u003e1.4 Online Safety Resources 15\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 2 Basic Concepts 19\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e2.1 Polarity and H-Bonds 19\u003c\/p\u003e \u003cp\u003e2.2 Physical Data 23\u003c\/p\u003e \u003cp\u003e2.3 Solvents 24\u003c\/p\u003e \u003cp\u003e2.4 Balancing Chemical Equations 26\u003c\/p\u003e \u003cp\u003e2.5 Concentration Units 28\u003c\/p\u003e \u003cp\u003e2.6 Moles and Millimoles 29\u003c\/p\u003e \u003cp\u003e2.7 Mineral Acids 31\u003c\/p\u003e \u003cp\u003e2.8 Calculation of Yields 32\u003c\/p\u003e \u003cp\u003e2.9 Scaling Up, Scaling Down 34\u003c\/p\u003e \u003cp\u003e2.10 Keeping Lab Books and Writing Lab Reports 34\u003c\/p\u003e \u003cp\u003e2.11 Chemical Literature 35\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 3 Basic Operations 45\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e3.1 Handling Liquids 45\u003c\/p\u003e \u003cp\u003e3.2 Heating 46\u003c\/p\u003e \u003cp\u003e3.3 Filtration 47\u003c\/p\u003e \u003cp\u003e3.4 Refluxing 51\u003c\/p\u003e \u003cp\u003e3.5 Evaporation 53\u003c\/p\u003e \u003cp\u003e3.6 Centrifugation 55\u003c\/p\u003e \u003cp\u003e3.7 Caring for Glassware 55\u003c\/p\u003e \u003cp\u003e3.8 Measuring Pressure 57\u003c\/p\u003e \u003cp\u003e\u003cb\u003eSection 2 The Experiments 59\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 4 Recrystallization and Melting Point 61\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e4.1 Overview 61\u003c\/p\u003e \u003cp\u003e4.2 Recrystallization 62\u003c\/p\u003e \u003cp\u003e4.3 Decolorizing Charcoal 69\u003c\/p\u003e \u003cp\u003e4.4 Recrystallization from Mixed Solvents 70\u003c\/p\u003e \u003cp\u003e4.5 Microscale Recrystallization 70\u003c\/p\u003e \u003cp\u003e4.6 Melting Point 71\u003c\/p\u003e \u003cp\u003e4.7 Sublimation 75\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 4 Recrystallization of Acetanilide and Urea 79\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE4.1 Recrystallization of Acetanilide 80\u003c\/p\u003e \u003cp\u003eE4.2 Microscale Recrystallization of Urea 82\u003c\/p\u003e \u003cp\u003eE4.3 Determination of Melting Points 82\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 5 Extraction 86\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction 86\u003c\/p\u003e \u003cp\u003e5.2 Solvent-Solvent Partitioning 86\u003c\/p\u003e \u003cp\u003e5.3 Macroscale Liquid-Liquid Extraction 92\u003c\/p\u003e \u003cp\u003e5.4 Microscale Liquid-Liquid Extraction 93\u003c\/p\u003e \u003cp\u003e5.5 Drying the Organic Layer 94\u003c\/p\u003e \u003cp\u003e5.6 Solid-Liquid Extraction 95\u003c\/p\u003e \u003cp\u003e5.7 Countercurrent Distribution 97\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 5 Isolation of Caffeine from Tea 103\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE5.1 Tea, Coffee, and Caffeine 103\u003c\/p\u003e \u003cp\u003eE5.2 Caffeine from Tea: Overview of the Experiment 105\u003c\/p\u003e \u003cp\u003eE5.3 Isolation of Caffeine 109\u003c\/p\u003e \u003cp\u003eE5.4 Purification of Caffeine by Sublimation 110\u003c\/p\u003e \u003cp\u003eE5.5 Purification of Caffeine by Recrystallization (Alternative Procedure) 111\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 6 Distillation — Separation and Purification of Organic Liquids 113\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e6.1 Boiling Point 113\u003c\/p\u003e \u003cp\u003e6.2 Boiling Point and Molecular Structure 114\u003c\/p\u003e \u003cp\u003e6.3 Simple Distillation 115\u003c\/p\u003e \u003cp\u003e6.4 Fractional Distillation 120\u003c\/p\u003e \u003cp\u003e6.5 Ideal and Nonideal Solutions 123\u003c\/p\u003e \u003cp\u003e6.6 Azeotropic Mixtures 124\u003c\/p\u003e \u003cp\u003e6.7 Fractionating Columns 125\u003c\/p\u003e \u003cp\u003e6.8 Microscale Distillation 126\u003c\/p\u003e \u003cp\u003e6.9 Boiling Point Determination 128\u003c\/p\u003e \u003cp\u003e6.10 Vacuum Distillation 129\u003c\/p\u003e \u003cp\u003e6.11 Steam Distillation 130\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 6A Distillation of Alcohols 136\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE6A.1 Distillation of Methanol from a Mixture with Ferric Chloride 136\u003c\/p\u003e \u003cp\u003eE6A.2 Separation of Methanol-Water by Simple Distillation 137\u003c\/p\u003e \u003cp\u003eE6A.3 Separation of Methanol-Water by Fractional Distillation 138\u003c\/p\u003e \u003cp\u003eE6A.4 Analysis of the Distillation Fractions by Density 139\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 6B Isolation of Anise Oil 142\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE6B.1 Overview 142\u003c\/p\u003e \u003cp\u003eE6B.2 Isolation of Anise Oil 142\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 7 Gas Chromatography 144\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction 144\u003c\/p\u003e \u003cp\u003e7.2 The Chromatographic Methods 144\u003c\/p\u003e \u003cp\u003e7.3 Partition Chromatography 146\u003c\/p\u003e \u003cp\u003e7.4 Gas Chromatography 149\u003c\/p\u003e \u003cp\u003e7.5 The Gas Chromatograph 151\u003c\/p\u003e \u003cp\u003e7.6 Measuring the Retention Time 155\u003c\/p\u003e \u003cp\u003e7.7 Integration 156\u003c\/p\u003e \u003cp\u003e7.8 Quantitative Analysis 157\u003c\/p\u003e \u003cp\u003e7.9 Quantitative Analysis: A Closer Look (Advanced Level) 158\u003c\/p\u003e \u003cp\u003e7.10 Qualitative Analysis 161\u003c\/p\u003e \u003cp\u003e7.11 Running GC: Step by Step 162\u003c\/p\u003e \u003cp\u003e7.12 Gas Chromatography Do’s and Don’ts 163\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 7A Gas Chromatography of Alcohols 167\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE7A.1 Analysis of Alcohols 167\u003c\/p\u003e \u003cp\u003eE7A.2 Separation of Methanol and Water 168\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 7B Analysis of Anise Oil 170\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE7B Analysis of Anise Oil 170\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 8 Thin-Layer Chromatography 172\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e8.1 Overview 172\u003c\/p\u003e \u003cp\u003e8.2 The Adsorption Process 173\u003c\/p\u003e \u003cp\u003e8.3 Selection of TLC Conditions 175\u003c\/p\u003e \u003cp\u003e8.4 Running TLC Plates 178\u003c\/p\u003e \u003cp\u003e8.5 Adsorption Isotherms (Advanced Level) 182\u003c\/p\u003e \u003cp\u003e8.6 Applications of TLC 184\u003c\/p\u003e \u003cp\u003e8.7 Other Stationary Phases 186\u003c\/p\u003e \u003cp\u003e8.8 TLC Do’s and Don’ts 186\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 8 TLC Analysis of Vegetable Extracts 190\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE8.1 Plant Pigments 190\u003c\/p\u003e \u003cp\u003eE8.2 Isolation and Analysis of Plant Pigments 192\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 9 Column Chromatography 197\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e9.1 Overview 197\u003c\/p\u003e \u003cp\u003e9.2 Practical Aspects 197\u003c\/p\u003e \u003cp\u003e9.3 Applications 202\u003c\/p\u003e \u003cp\u003e9.4 Column Chromatography Do’s and Don’ts 203\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 9 Isolation of C\u003csub\u003e60\u003c\/sub\u003e from Fullerene Soot 206\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE9.1 Fullerenes 206\u003c\/p\u003e \u003cp\u003eE9.2 Isolation of Fullerenes 207\u003c\/p\u003e \u003cp\u003eE9.3 A Chemical Test for Fullerenes 208\u003c\/p\u003e \u003cp\u003eE9.4 Overview of the Experiment 209\u003c\/p\u003e \u003cp\u003eE9.5 Isolation of C\u003csub\u003e60\u003c\/sub\u003e from Fullerene Soot 209\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 10 High-Performance Liquid Chromatography 214\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e10.1 Overview 214\u003c\/p\u003e \u003cp\u003e10.2 HPLC Systems 214\u003c\/p\u003e \u003cp\u003e10.3 HPLC Versus GC 215\u003c\/p\u003e \u003cp\u003e10.4 Solvents 216\u003c\/p\u003e \u003cp\u003e10.5 Pumps 217\u003c\/p\u003e \u003cp\u003e10.6 Injection Port 217\u003c\/p\u003e \u003cp\u003e10.7 Columns 218\u003c\/p\u003e \u003cp\u003e10.8 Detectors 219\u003c\/p\u003e \u003cp\u003e10.9 Why is HPLC High Performance? 220\u003c\/p\u003e \u003cp\u003e10.10 Reversed-Phase Chromatography 221\u003c\/p\u003e \u003cp\u003e10.11 Other Chemically Bonded Stationary Phases 222\u003c\/p\u003e \u003cp\u003e10.12 Size-Exclusion Chromatography 223\u003c\/p\u003e \u003cp\u003e10.13 Quantitative Determinations: Standard Curve Method 224\u003c\/p\u003e \u003cp\u003e10.14 HPLC Do’s and Don’ts 224\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 10 Vitamin Analysis—A Quantitative Study 227\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE10.1 Water-Soluble and Fat-Soluble Vitamins 227\u003c\/p\u003e \u003cp\u003eE10.2 Vitamin Stability 229\u003c\/p\u003e \u003cp\u003eE10.3 International Units 230\u003c\/p\u003e \u003cp\u003eE10.4 Characterization of Vitamin A 230\u003c\/p\u003e \u003cp\u003eE10.5 Overview of the Experiment 231\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 11 Refractometry and Polarimetry 238\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e11.1 Refractive Index 238\u003c\/p\u003e \u003cp\u003e11.2 The Refractometer 239\u003c\/p\u003e \u003cp\u003e11.3 Measuring the Refractive Index 240\u003c\/p\u003e \u003cp\u003e11.4 Polarimetry 242\u003c\/p\u003e \u003cp\u003e11.5 The Polarimeter 245\u003c\/p\u003e \u003cp\u003e11.6 Measuring the Optical Rotation 246\u003c\/p\u003e \u003cp\u003e11.7 Optical Rotation of Mixtures 247\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 11A Analysis of Essential Oils 250\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE11A.1 Terpenoids 250\u003c\/p\u003e \u003cp\u003eE11A.2 Essential Oils 252\u003c\/p\u003e \u003cp\u003eE11A.3 Specific Rotation 253\u003c\/p\u003e \u003cp\u003eE11A.4 Refractive Index 253\u003c\/p\u003e \u003cp\u003eE11A.5 Composition of Essential Oils 253\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 11B Separation of Carvone and Limonene 255\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE11B.1 Carvone and Limonene 255\u003c\/p\u003e \u003cp\u003eE11B.2 Analysis of the Crude Oils 256\u003c\/p\u003e \u003cp\u003eE11B.3 Separation of Carvone and Limonene 257\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 12 Alcohols and Alkenes 261\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e12.1 Alkenes from Alcohols 261\u003c\/p\u003e \u003cp\u003e12.2 Dehydration Mechanisms 262\u003c\/p\u003e \u003cp\u003e12.3 Characterization of Alkenes 264\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 12 The Dehydration of Methylcyclohexanols 268\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE12.1 Overview 268\u003c\/p\u003e \u003cp\u003eE12.2 Dehydration of Methylcyclohexanols 269\u003c\/p\u003e \u003cp\u003eE12.3 Analysis of the Product Mixture 270\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 13 Alkyl Halides 273\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e13.1 Preparation 273\u003c\/p\u003e \u003cp\u003e13.2 Reactions 274\u003c\/p\u003e \u003cp\u003e13.3 Alkyl Halides from Alcohols 274\u003c\/p\u003e \u003cp\u003e13.4 Characterization Tests 276\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 13 Synthesis of \u003ci\u003en\u003c\/i\u003e-ButyI Bromide and 2-ChIoro-2-MethyIbutane 280\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE13.1 Synthesis of \u003ci\u003en\u003c\/i\u003e-Buty1 Bromide 280\u003c\/p\u003e \u003cp\u003eE13.2 Synthesis of 2-Ch1oro-2-Methy1butane 284\u003c\/p\u003e \u003cp\u003eE13.3 Characterizahon Tests 285\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 14 Acid-Base Extraction 292\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e14.1 Introduction 292\u003c\/p\u003e \u003cp\u003e14.2 Acids and Bases 292\u003c\/p\u003e \u003cp\u003e14.3 Structural Effects on Acid-Base Properties 294\u003c\/p\u003e \u003cp\u003e14.4 Acid-Base Extraction 298\u003c\/p\u003e \u003cp\u003e14.5 Overview 303\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 14A Isolation of Eugenol from Cloves 307\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE14A.1 Ancient Medicine 307\u003c\/p\u003e \u003cp\u003eE14A.2 Eugenol from Cloves: Overview of the Experiment 307\u003c\/p\u003e \u003cp\u003eE14A.3 Isolation of Eugenol 308\u003c\/p\u003e \u003cp\u003eE14A.4 GC and IR Analyses 310\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 14B Isolation of the Active Ingredients in an Analgesic Tablet 315\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE14B.1 Overview 315\u003c\/p\u003e \u003cp\u003eE14B.2 Separation of the Active Ingredients in Excedrin 317\u003c\/p\u003e \u003cp\u003eE14B.3 Analysis 317\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 15 Phenols and Ethers 323\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e15.1 Phenols and Ethers 323\u003c\/p\u003e \u003cp\u003e15.2 Williamson Ether Synthesis 323\u003c\/p\u003e \u003cp\u003e15.3 Characterization of Phenols: Ferric Chloride Test 324\u003c\/p\u003e \u003cp\u003e15.4 IR and NMR of Phenols and Ethers 325\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 15 Medicinal Chemistry: From Tylenol to a Banned Chemical 327\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE15.1 Analgesics 327\u003c\/p\u003e \u003cp\u003eE15.2 The Experiment: Overview 329\u003c\/p\u003e \u003cp\u003eE15.3 Conversion of Acetaminophen into Phenacetin 330\u003c\/p\u003e \u003cp\u003eE15.4 Ferric Chloride Test 332\u003c\/p\u003e \u003cp\u003eE15.5 Analysis of Analgesics by TLC 332\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 16 Electrophilic Aromatic Substitution 336\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e16.1 Mechanism of Electrophilic Aromatic Substitution 336\u003c\/p\u003e \u003cp\u003e16.2 Nitration and Halogenation 337\u003c\/p\u003e \u003cp\u003e16.3 Effects of Substituents 338\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 16A lodinatian of Tyrosine 342\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE16A.1 Synthesis of 3,5-Diiodotyrosine 342\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 16B Two Substitution Puzzles 350\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE16B.1 Overview 350\u003c\/p\u003e \u003cp\u003eE16B.2 NMR Analysis 351\u003c\/p\u003e \u003cp\u003eE16B.3 Nitration of Phenacetin 352\u003c\/p\u003e \u003cp\u003eE16B.4 Bromination of Phenacetin 353\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 17 Nucleophilic Aromatic Substitution 355\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e17.1 Nucleophilic Aromatic Substitution 355\u003c\/p\u003e \u003cp\u003e17.2 Dinitroanilines 356\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 17 Dinitrocompounds—Herbicides 360\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE17.1 Synthesis of Trifluralin 360\u003c\/p\u003e \u003cp\u003eE17.2 Synthesis of \u003ci\u003eN\u003c\/i\u003e -(\u003ci\u003en\u003c\/i\u003e-Buty1) -2,4-Dinitroani1ine 361\u003c\/p\u003e \u003cp\u003eE17.3 Herbicide Effects of Trifluralin and \u003ci\u003eN\u003c\/i\u003e -(\u003ci\u003en\u003c\/i\u003e-Butyl) -2,4-Dinitroaniline 362\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 18 Chemical Kinetics 368\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e18.1 Mechanistic Studies 368\u003c\/p\u003e \u003cp\u003e18.2 Chemical Kinetics 368\u003c\/p\u003e \u003cp\u003e18.3 Experimental Aspects 370\u003c\/p\u003e \u003cp\u003e18.4 Integrated Rate Equations 370\u003c\/p\u003e \u003cp\u003e18.5 Reaction Half-Life 372\u003c\/p\u003e \u003cp\u003e18.6 Transition States 372\u003c\/p\u003e \u003cp\u003e18.7 Dependence of the Rate Constant with Temperature: Arrhenius Equation 375\u003c\/p\u003e \u003cp\u003e18.8 Following the Kinetics 375\u003c\/p\u003e \u003cp\u003e18.9 Best Fit 377\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 18 Nucleophilic Aromatic Substitution Kinetics 381 \u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE18.1 The Problem 381\u003c\/p\u003e \u003cp\u003eE18.2 To Follow the Kinetics 383\u003c\/p\u003e \u003cp\u003eE18.3 Overview of the Experiment 383\u003c\/p\u003e \u003cp\u003eE18.4 Synthesis of 2,4-Dinitroanisole 384\u003c\/p\u003e \u003cp\u003eE18.5 Visible Spectrum of \u003ci\u003eN\u003c\/i\u003e-(\u003ci\u003en\u003c\/i\u003e-Butyl) -2,4-Dinitroaniline 384\u003c\/p\u003e \u003cp\u003eE18.6 Beer’s Law of \u003ci\u003eN\u003c\/i\u003e-(\u003ci\u003en\u003c\/i\u003e-Butyl) -2,4-Dinitroaniline 385\u003c\/p\u003e \u003cp\u003eE18.7 Kinetics of the Reaction of 2,4-Dinitroanisole with \u003ci\u003en\u003c\/i\u003e-Butylamine in Methanol 385\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 19 Diels-Alder Reaction 391\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e19.1 Diels—Alder Reaction 391\u003c\/p\u003e \u003cp\u003e19.2 Endo versus Exo 392\u003c\/p\u003e \u003cp\u003e19.3 Solvent Effects 393\u003c\/p\u003e \u003cp\u003e19.4 Experimental Considerations: Following the Reaction 395\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 19A Diels—Alder Reactions in Toluene 398\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE19A.1 Reaction of 9-Anthraldehyde with Maleic Anhydride 398\u003c\/p\u003e \u003cp\u003eE19A.2 Reaction of Phencyclone with Norbornadiene 400\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 19B Diels—Alder Reaction in Water 408\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE19B.1 Reaction of 9-Anthracenemethanol with \u003ci\u003eN\u003c\/i\u003e-Ethylmaleimide 408\u003c\/p\u003e \u003cp\u003eE19B.2 Kinetics of the Reaction of 9-Anthracenemethanol with NEM 409\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 20 Aldehydes and Ketones 415\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e20.1 Introduction 415\u003c\/p\u003e \u003cp\u003e20.2 Preparation 416\u003c\/p\u003e \u003cp\u003e20.3 Reactions of Aldehydes and Ketones 416\u003c\/p\u003e \u003cp\u003e20.4 IR and NMR of Aldehydes and Ketones 423\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 20A Identification of Aldehydes and Ketones 427\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE20A.1 Characterization Tests 428\u003c\/p\u003e \u003cp\u003eE20A.2 Preparation of Derivatives 430\u003c\/p\u003e \u003cp\u003eE20A.3 The Unknown 430\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 20B Synthesis of \u003ci\u003etrans\u003c\/i\u003e-Cinnamic Acid 433 \u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE20B Synthesis of \u003ci\u003etrans\u003c\/i\u003e-Cinnamic Acid: Perkin Condensation, 433\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 21 Oxidation-Reduction 438 \u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e21.1 Overview 438\u003c\/p\u003e \u003cp\u003e21.2 Selectivity 439\u003c\/p\u003e \u003cp\u003e21.3 Oxidations 440\u003c\/p\u003e \u003cp\u003e21.4 Phase Transfer Catalysis 444\u003c\/p\u003e \u003cp\u003e21.5 Reductions 445\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 21 Oxidation-Reduction 451\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE21.1 Reduction of Benzophenone 451\u003c\/p\u003e \u003cp\u003eE21.2 Oxidation of Benzhydrol 452\u003c\/p\u003e \u003cp\u003eE21.3 Reduction of \u003ci\u003etrans\u003c\/i\u003e-Cinnamaldehyde 453\u003c\/p\u003e \u003cp\u003eE21.4 Oxidation of \u003ci\u003etrans\u003c\/i\u003e-Cinnamyl Alcohol 454\u003c\/p\u003e \u003cp\u003eE21.5 Reduction of Camphor 455\u003c\/p\u003e \u003cp\u003eE21.6 Oxidation of Isoborneol 456\u003c\/p\u003e \u003cp\u003eE21.7 Synthesis of Terephthalic Acid 456\u003c\/p\u003e \u003cp\u003eE21.8 Monoreduction of \u003ci\u003em\u003c\/i\u003e-Dinitrobenzene 458\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 22 Esters 473\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e22.1 Esters in Nature and Society 473\u003c\/p\u003e \u003cp\u003e22.2 Preparation of Esters 474\u003c\/p\u003e \u003cp\u003e22.3 Acetylation 476\u003c\/p\u003e \u003cp\u003e22.4 Ester Hydrolysis 476\u003c\/p\u003e \u003cp\u003e22.5 Characterization of Esters 477\u003c\/p\u003e \u003cp\u003e22.6 IR and NMR of Esters and Carboxylic Acids 477\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 22A Preparation of Fruity Fragrances 480\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE22A.1 Preparation of Methyl \u003ci\u003etrans\u003c\/i\u003e-Cirinamate: A Component of Strawberry Aroma 480\u003c\/p\u003e \u003cp\u003eE22A.2 Preparation of \u003ci\u003en\u003c\/i\u003e-Propy1 Acetate and Isoamyl Acetate 482\u003c\/p\u003e \u003cp\u003eE22A.3 Hydroxamic Acid Test 484\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 22B Transforming Bengay into Aspirin 491\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE22B.1 Overview 491\u003c\/p\u003e \u003cp\u003eE22B.2 Separation of Methyl Salicylate, 493\u003c\/p\u003e \u003cp\u003eE22B.3 Hydrolysis of Methyl Salicylate, 493\u003c\/p\u003e \u003cp\u003eE22B.4 Synthesis of Aspirin 494\u003c\/p\u003e \u003cp\u003eE22B.5 Analysis 494\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 23 Multistep Synthesis 499\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e23.1 Overview 499\u003c\/p\u003e \u003cp\u003e23.2 Multistep Synthesis 500\u003c\/p\u003e \u003cp\u003e23.3 Retrosynthetic Analysis 502\u003c\/p\u003e \u003cp\u003e23.4 Planning a Multistep Synthesis 507\u003c\/p\u003e \u003cp\u003e23.5 Linear versus Convergent Synthesis 508\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 23A Synthesis of an Ant Alarm Pheromone: 2-Methyl-4-Heptanone 511\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE23A.1 Overview 511\u003c\/p\u003e \u003cp\u003eE23A.2 Synthetic Route 511\u003c\/p\u003e \u003cp\u003eE23A.3 Grignard Reactions 512\u003c\/p\u003e \u003cp\u003eE23A.4 Oxidation of Secondary Alcohols 514\u003c\/p\u003e \u003cp\u003eE23A.5 Synthesis of 2-Methyl-4-Heptanol 514\u003c\/p\u003e \u003cp\u003eE23A.6 Synthesis of 2-Methyl-4-Heptanone 516\u003c\/p\u003e \u003cp\u003eE23A.7 Vacuum Distillation 516\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 23B Synthesis of Ionones: An Open-Ended Experiment 520\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE23B.1 lonones 520\u003c\/p\u003e \u003cp\u003eE23B.2 Synthetic Pathway 520\u003c\/p\u003e \u003cp\u003eE23B.3 Characterization of lonones 522\u003c\/p\u003e \u003cp\u003eE23B.4 Preparation of Pseudoionones 523\u003c\/p\u003e \u003cp\u003eE23B.5 Cyclization with Sulfuric Acid-Acetic Acid 524\u003c\/p\u003e \u003cp\u003eE23B.6 Cyclization with Phosphoric Acid 525\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 24 Molecules of Life 532\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e24.1 Proteins 532\u003c\/p\u003e \u003cp\u003e24.2 Carbohydrates 539\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 24 Chemistry of Milk 546\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE24.1 Composition of Milk 546\u003c\/p\u003e \u003cp\u003eE24.2 Isolation and Characterization of Casein 549\u003c\/p\u003e \u003cp\u003eE24.3 Isolation and Characterization of Lactose 552\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 25 Lipids 556\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e25.1 Fats and Oils 556\u003c\/p\u003e \u003cp\u003e25.2 Characterization of Oils 558\u003c\/p\u003e \u003cp\u003e25.3 Uncommon Fatty Acids and Related Compounds 559\u003c\/p\u003e \u003cp\u003e25.4 Saponification 560\u003c\/p\u003e \u003cp\u003e25.5 Steroids 560\u003c\/p\u003e \u003cp\u003e25.6 Bile Acids 562\u003c\/p\u003e \u003cp\u003e25.7 Inclusion Compounds 562\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 25 Lipids 566\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE25.1 Analysis of Oils 566\u003c\/p\u003e \u003cp\u003eE25.2 Trimyristin From Nutmeg 567\u003c\/p\u003e \u003cp\u003eE25.3 Preparation of Azelaic Acid from Castor Oil 569\u003c\/p\u003e \u003cp\u003eE25.4 Urea Complexes of Fatty Acids 570\u003c\/p\u003e \u003cp\u003eE25.5 Solubility of Cholesterol 570\u003c\/p\u003e \u003cp\u003eE25.6 Bile Acids 571\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 26 Polymers 577\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e26.1 Introduction 577\u003c\/p\u003e \u003cp\u003e26.2 Chain-Reaction Polymerization 579\u003c\/p\u003e \u003cp\u003e26.3 Step-Reaction Polymerization 581\u003c\/p\u003e \u003cp\u003e26.4 Polymer Structure 583\u003c\/p\u003e \u003cp\u003e26.5 Some Typical Polymers 584\u003c\/p\u003e \u003cp\u003e26.6 Plasticizers 588\u003c\/p\u003e \u003cp\u003e26.7 Applications and Recycling 589\u003c\/p\u003e \u003cp\u003e26.8 Identification of Plastics 590\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 26 Synthesis and Analysis of Polymers 595 \u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE26.1 Overview 595\u003c\/p\u003e \u003cp\u003eE26.2 Emulsion Polymerization of Styrene with Persulfate 596\u003c\/p\u003e \u003cp\u003eE26.3 Emulsion Polymerization of Methyl Methacrylate 597\u003c\/p\u003e \u003cp\u003eE26.4 Bulk Copolymerization of Styrene and Divinylbenzene: Effect of a Plasticizer 598\u003c\/p\u003e \u003cp\u003eE26.5 Bulk Polymerization of Methyl Methacrylate 599\u003c\/p\u003e \u003cp\u003eE26.6 Cellulose Triacetate 599\u003c\/p\u003e \u003cp\u003eE26.7 Phenolic Resins 601\u003c\/p\u003e \u003cp\u003eE26.8 Preparation of Nylon 6.6: The Nylon Rope Trick 601\u003c\/p\u003e \u003cp\u003eE26.9 Analysis of Polymers 602\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 27 Dyes and Pigments\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e27.1 Dyes, Pigments, and Colors 611\u003c\/p\u003e \u003cp\u003e27.2 Azo Dyes 612\u003c\/p\u003e \u003cp\u003e27.3 Synthesis of Azo Dyes 613\u003c\/p\u003e \u003cp\u003e27.4 Cationic Dyes 615\u003c\/p\u003e \u003cp\u003e27.5 Anthraquinone Dyes 616\u003c\/p\u003e \u003cp\u003e27.6 Indigo Dyes 617\u003c\/p\u003e \u003cp\u003e27.7 Other Dyes 618\u003c\/p\u003e \u003cp\u003e27.8 Mode of Application 619\u003c\/p\u003e \u003cp\u003e27.9 Dyeing 620\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 27 Colored Chemistry 626\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE27.1 Direct Dyes 627\u003c\/p\u003e \u003cp\u003eE27.2 Mordant Dyeing 630\u003c\/p\u003e \u003cp\u003eE27.3 Ingrain Dyes 630\u003c\/p\u003e \u003cp\u003eE27.4 Vat Dyes 632\u003c\/p\u003e \u003cp\u003eE27.5 Dye Fastness 633\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 28 Bioorganic Chemistry 635\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e28.1 Enzymes: Biological Catalysts 635\u003c\/p\u003e \u003cp\u003e28.2 How Enzymes Work 635\u003c\/p\u003e \u003cp\u003e28.3 Using Enzymes 637\u003c\/p\u003e \u003cp\u003e28.4 Prochiral Molecules 639\u003c\/p\u003e \u003cp\u003e28.5 Reduction of Ketones 640\u003c\/p\u003e \u003cp\u003e28.6 Enantiomeric Excess 642\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 28 Asymmetric Synthesis with Baker’s Yeast: An Open-Ended Experiment 645\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE28.1 Overview 645\u003c\/p\u003e \u003cp\u003eE28.2 Investigating the Course of the Reaction 646\u003c\/p\u003e \u003cp\u003eE28.3 Conformational Analysis: Determining Whether the Diol is \u003ci\u003eThreo\u003c\/i\u003e or \u003ci\u003eErythro\u003c\/i\u003e (Advanced Level) 647\u003c\/p\u003e \u003cp\u003eE28.4 Reduction of 1-Pheny1-1,2-Propanedione with Baker’s Yeast 649\u003c\/p\u003e \u003cp\u003eE28.5 Analysis 650\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 29 Molecules of Heredity 653\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e29.1 Nucleosides and Nucleotides 653\u003c\/p\u003e \u003cp\u003e29.2 Base Pairing 656\u003c\/p\u003e \u003cp\u003e29.3 Purine and Pyrimidine Bases 657\u003c\/p\u003e \u003cp\u003e29.4 Chemical Transformations 658\u003c\/p\u003e \u003cp\u003e\u003cb\u003eExperiment 29 Analysis of Nucleosides 662\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eE29.1 Overview of the Experiment 662\u003c\/p\u003e \u003cp\u003eE29.2 Analysis of an RNA Digest 662\u003c\/p\u003e \u003cp\u003eE29.3 Deamination of Cytidine to Uridine 664\u003c\/p\u003e \u003cp\u003e\u003cb\u003eSection 3 Spectroscopy 667\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 30 Absorption Spectroscopy 669\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e30.1 The Nature of Light 669\u003c\/p\u003e \u003cp\u003e30.2 Interaction between Electromagnetic Radiation and Matter 670\u003c\/p\u003e \u003cp\u003e30.3 Absorption Spectroscopy 672\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 31 Infrared Spectroscopy 675\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e31.1 Molecular Vibrations 675\u003c\/p\u003e \u003cp\u003e31.2 Stretching and Bending Vibrations 677\u003c\/p\u003e \u003cp\u003e31.3 IR and Dipole Moment 679\u003c\/p\u003e \u003cp\u003e31.4 Regions of the IR Spectrum 680\u003c\/p\u003e \u003cp\u003e31.5 Experimental Aspects 681\u003c\/p\u003e \u003cp\u003e31.6 Interpreting IR Spectra 685\u003c\/p\u003e \u003cp\u003e31.7 Case Studies 693\u003c\/p\u003e \u003cp\u003e31.8 Concentration and Solvent Effects on IR 695\u003c\/p\u003e \u003cp\u003e31.9 Instrumentation 697\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 32 Ultraviolet-Visible Spectroscopy 707\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e32.1 Electronic Transitions 707\u003c\/p\u003e \u003cp\u003e32.2 Chromophores and Auxochromes 709\u003c\/p\u003e \u003cp\u003e32.3 Structural Effects on UV-Visible Spectra: Woodward—Fieser Rules 710\u003c\/p\u003e \u003cp\u003e32.4 Applications of UV-Visible Spectroscopy 711\u003c\/p\u003e \u003cp\u003e32.5 Spectrophotometers 714\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 33 Nuclear Magnetic Resonance 719\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e33.1 Nuclear Spin 719\u003c\/p\u003e \u003cp\u003e33.2 The Resonance Phenomenon: A Closer Look 721\u003c\/p\u003e \u003cp\u003e33.3 Obtaining the NMR Spectrum 724\u003c\/p\u003e \u003cp\u003e33.4 \u003csup\u003e1\u003c\/sup\u003eH-NMR 726\u003c\/p\u003e \u003cp\u003e33.5 Electronic Shielding 727\u003c\/p\u003e \u003cp\u003e33.6 The Chemical Shift 729\u003c\/p\u003e \u003cp\u003e33.7 Effect of Pi Electrons 730\u003c\/p\u003e \u003cp\u003e33.8 Hydrogen Equivalence: A Closer Look 732\u003c\/p\u003e \u003cp\u003e33.9 Integrals 732\u003c\/p\u003e \u003cp\u003e33.10 Spin-Spin Splitting 734\u003c\/p\u003e \u003cp\u003e33.11 Typical Coupling Patterns 739\u003c\/p\u003e \u003cp\u003e33.12 The Coupling Constant 739\u003c\/p\u003e \u003cp\u003e33.13 Coupling: A Closer Look 742\u003c\/p\u003e \u003cp\u003e33.14 Chemical Shift Correlations 750\u003c\/p\u003e \u003cp\u003e33.15 Coupling of Hydrogens Attached to Heteroatoms 756\u003c\/p\u003e \u003cp\u003e33.16 \u003csup\u003e13\u003c\/sup\u003eC-NMR 758\u003c\/p\u003e \u003cp\u003e33.17 \u003csup\u003e13\u003c\/sup\u003eC-NMR Chemical Shifts 760\u003c\/p\u003e \u003cp\u003e33.18 Aromatic Systems 765\u003c\/p\u003e \u003cp\u003e33.19 Effect of Chirality on the NMR 768\u003c\/p\u003e \u003cp\u003e33.20 Running the Spectrum 771\u003c\/p\u003e \u003cp\u003e33.21 Two-Dimensional NMR 772\u003c\/p\u003e \u003cp\u003e33.22 Interpreting \u003csup\u003e1\u003c\/sup\u003eH-NMR Spectra 774\u003c\/p\u003e \u003cp\u003e\u003cb\u003eUnit 34 Mass Spectrometry 783\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e34.1 Overview 783\u003c\/p\u003e \u003cp\u003e34.2 Instrumentation 784\u003c\/p\u003e \u003cp\u003e34.3 The Molecular Ion 785\u003c\/p\u003e \u003cp\u003e34.4 Charge Localization 789\u003c\/p\u003e \u003cp\u003e34.5 Fragmentations 790\u003c\/p\u003e \u003cp\u003e34.6 MS Case Studies 796\u003c\/p\u003e \u003cp\u003e34.7 Interpreting Mass Spectra 798\u003c\/p\u003e \u003cp\u003e34.8 High-Resolution Mass Spectra 800\u003c\/p\u003e \u003cp\u003eAnswers to Odd-Numbered Exercises 803\u003c\/p\u003e \u003cp\u003eCredits 821\u003c\/p\u003e \u003cp\u003eIndex 823\u003c\/p\u003e \u003cp\u003eIndex of Spectra 834\u003c\/p\u003e","brand":"John Wiley \u0026 Sons Inc","offers":[{"title":"Default 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