{"product_id":"microscale-organic-laboratory-with-multistep-and-multiscale-syntheses-6e-9781118083406","title":"Microscale Organic Laboratory with Multistep and","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003e\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cb\u003eChapter 1 INTRODUCTION 1 General Rules for the Microscale Laboratory 3\u003c\/b\u003e  \u003cp\u003eThe Organic Chemistry Laboratory 4\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 2 SAFETY 5\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eMaking the Laboratory a Safer Place 5\u003c\/p\u003e \u003cp\u003eNature of Hazards 5\u003c\/p\u003e \u003cp\u003eReduction of Risks 6\u003c\/p\u003e \u003cp\u003ePrecautionary Measures 7\u003c\/p\u003e \u003cp\u003eThinking About the Risks In Using Chemicals 8\u003c\/p\u003e \u003cp\u003eDisposal of Chemicals 8\u003c\/p\u003e \u003cp\u003eMaterial Safety Data Sheets 9\u003c\/p\u003e \u003cp\u003eAlternate Sources of Information 12\u003c\/p\u003e \u003cp\u003eEstimating Risks from Vapors 13\u003c\/p\u003e \u003cp\u003eMicrowave Safety 14\u003c\/p\u003e \u003cp\u003eConcluding Thoughts 15\u003c\/p\u003e \u003cp\u003eGeneral Safety References 16\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 3 INTRODUCTION TO MICROSCALE ORGANIC LABORATORY EQUIPMENT AND TECHNIQUES 18\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eMicroglassware Equipment 19\u003c\/p\u003e \u003cp\u003eStandard Taper Joints 19\u003c\/p\u003e \u003cp\u003eConical Vials 20\u003c\/p\u003e \u003cp\u003eCondensers 20\u003c\/p\u003e \u003cp\u003eDistillation Heads 20\u003c\/p\u003e \u003cp\u003eRecrystallization Tubes 20\u003c\/p\u003e \u003cp\u003eMiscellaneous Items 20\u003c\/p\u003e \u003cp\u003eGas Chromatographic Fraction Collection Items 21\u003c\/p\u003e \u003cp\u003eStandard Experimental Apparatus 21\u003c\/p\u003e \u003cp\u003eHeating and Stirring Arrangements 21\u003c\/p\u003e \u003cp\u003eSand Bath Technique—Hot Plate Calibration 21\u003c\/p\u003e \u003cp\u003eMetal Heat-Transfer Devices 22\u003c\/p\u003e \u003cp\u003eStirring 22\u003c\/p\u003e \u003cp\u003eReflux Apparatus 23\u003c\/p\u003e \u003cp\u003eDistillation Apparatus 24\u003c\/p\u003e \u003cp\u003eMoisture-Protected Reaction Apparatus 25\u003c\/p\u003e \u003cp\u003eSpecialized Pieces of Equipment 26\u003c\/p\u003e \u003cp\u003eMicrowave Heating as a Tool for Organic Chemistry 27\u003c\/p\u003e \u003cp\u003eIntroduction 27\u003c\/p\u003e \u003cp\u003eApplications 32\u003c\/p\u003e \u003cp\u003eEquipment Available 34\u003c\/p\u003e \u003cp\u003eExperimental Protocols 35\u003c\/p\u003e \u003cp\u003eMicroscale Laws 35\u003c\/p\u003e \u003cp\u003eRules of the Trade for Handling Organic Materials at the Microscale Level 35\u003c\/p\u003e \u003cp\u003eRules for Working with Liquids at the Microscale Level 36\u003c\/p\u003e \u003cp\u003eRules for Working with Solids at the Microscale Level 39\u003c\/p\u003e \u003cp\u003eThe Laboratory Notebook 40\u003c\/p\u003e \u003cp\u003eExample of a Laboratory Notebook Entry 41\u003c\/p\u003e \u003cp\u003eCalculating Yields 42\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 4 DETERMINATION OF PHYSICAL PROPERTIES 45\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eLiquids 46\u003c\/p\u003e \u003cp\u003eUltramicro Boiling Point 46\u003c\/p\u003e \u003cp\u003eDensity 50\u003c\/p\u003e \u003cp\u003eSolids 51\u003c\/p\u003e \u003cp\u003eMelting Points 51\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 5 MICROSCALE LABORATORY TECHNIQUES 55\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eTECHNIQUE 1 Gas Chromatography 55\u003c\/p\u003e \u003cp\u003eGC Instrumentation 56\u003c\/p\u003e \u003cp\u003eTECHNIQUE 2 Simple Distillation 61\u003c\/p\u003e \u003cp\u003eTECHNIQUE 3 Fractional Distillation 64\u003c\/p\u003e \u003cp\u003eTECHNIQUE 4 Solvent Extraction 67\u003c\/p\u003e \u003cp\u003eIntermolecular Properties: Solubility 67\u003c\/p\u003e \u003cp\u003ePartition (or Distribution) Coefficient 70\u003c\/p\u003e \u003cp\u003eExtraction 72\u003c\/p\u003e \u003cp\u003eSolid–Liquid Extraction 79\u003c\/p\u003e \u003cp\u003eDrying Agents 80\u003c\/p\u003e \u003cp\u003eSolid-Phase Extraction 83\u003c\/p\u003e \u003cp\u003eTECHNIQUE 5 Crystallization 85\u003c\/p\u003e \u003cp\u003eGeneral Crystallization Procedure 85\u003c\/p\u003e \u003cp\u003eSimple Crystallization 87\u003c\/p\u003e \u003cp\u003eFiltration Techniques 88\u003c\/p\u003e \u003cp\u003e\u003cb\u003eTECHNIQUE 6 Chromatography 92\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eColumn, Flash, High-Performance Liquid, and Thin-Layer Chromatography 92\u003c\/p\u003e \u003cp\u003eColumn Chromatography 92\u003c\/p\u003e \u003cp\u003eFlash Chromatography 95\u003c\/p\u003e \u003cp\u003eThin-Layer Chromatography 97\u003c\/p\u003e \u003cp\u003ePaper Chromatography 99\u003c\/p\u003e \u003cp\u003eHigh-Performance Liquid Chromatography 100\u003c\/p\u003e \u003cp\u003eTECHNIQUE 6B Concentration of Solutions 101\u003c\/p\u003e \u003cp\u003eDistillation 102\u003c\/p\u003e \u003cp\u003eEvaporation with Nitrogen Gas 102\u003c\/p\u003e \u003cp\u003eRemoval of Solvent Under Reduced Pressure 102\u003c\/p\u003e \u003cp\u003e\u003cb\u003eTECHNIQUE 7 Collection or Control of Gaseous Products 105\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eWater-Insoluble Gases 105\u003c\/p\u003e \u003cp\u003eTrapping Byproduct Gases 106\u003c\/p\u003e \u003cp\u003eTECHNIQUE 8 Measurement of Specific Rotation 108\u003c\/p\u003e \u003cp\u003eTheory 108\u003c\/p\u003e \u003cp\u003eThe Polarimeter 109\u003c\/p\u003e \u003cp\u003eTECHNIQUE 9 Sublimation 111\u003c\/p\u003e \u003cp\u003eSublimation Theory 112\u003c\/p\u003e \u003cp\u003eExperimental Setup 113\u003c\/p\u003e \u003cp\u003ePrecautions 113\u003c\/p\u003e \u003cp\u003eChapter 6 MICROSCALE ORGANIC LABORATORY EXPERIMENTS 115\u003c\/p\u003e \u003cp\u003eEXPERIMENT 1 Getting to Know You: Measurement of Physical Properties 116\u003c\/p\u003e \u003cp\u003eDiscussion 117\u003c\/p\u003e \u003cp\u003eExperimental Procedure 118\u003c\/p\u003e \u003cp\u003eMelting Point 118\u003c\/p\u003e \u003cp\u003eEXPERIMENT 2 The Separation of a 25-L Mixture of Heptanal (bp 153 C) and Cyclohexanol (bp 160 C) by Gas Chromatography 123\u003c\/p\u003e \u003cp\u003eDiscussion 123\u003c\/p\u003e \u003cp\u003eCollection Yield 124\u003c\/p\u003e \u003cp\u003eCollection Yield 125\u003c\/p\u003e \u003cp\u003eComponents 126\u003c\/p\u003e \u003cp\u003eExperimental Procedure 126\u003c\/p\u003e \u003cp\u003eEXPERIMENT 3 Distillation 129\u003c\/p\u003e \u003cp\u003eExperiment 3A Simple Distillation at the Semimicroscale\u003c\/p\u003e \u003cp\u003eLevel: Separation of Ethyl Acetate from trans-1,2-Dibenzoylethylene 130\u003c\/p\u003e \u003cp\u003eDiscussion 130\u003c\/p\u003e \u003cp\u003eComponents 130\u003c\/p\u003e \u003cp\u003eExperimental Procedure 131\u003c\/p\u003e \u003cp\u003eExperiment 3B Fractional Semimicroscale Distillation: Separation of Hexane and Toluene 132\u003c\/p\u003e \u003cp\u003eDiscussion 133\u003c\/p\u003e \u003cp\u003eComponents 133\u003c\/p\u003e \u003cp\u003eExperimental Procedure 133\u003c\/p\u003e \u003cp\u003eExperiment 3C Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning-Band Column 135\u003c\/p\u003e \u003cp\u003eDiscussion 135\u003c\/p\u003e \u003cp\u003eComponents 136\u003c\/p\u003e \u003cp\u003eExperimental Procedure 136\u003c\/p\u003e \u003cp\u003eExperiment 3D Fractional Semimicroscale Distillation: The Separation of 2-Methylpentane and Cyclohexane Using a Spinning Band in a Hickman–Hinkle Still 138\u003c\/p\u003e \u003cp\u003eDiscussion 139\u003c\/p\u003e \u003cp\u003eComponents 139\u003c\/p\u003e \u003cp\u003eExperimental Procedure 139\u003c\/p\u003e \u003cp\u003eEXPERIMENT 4 Solvent Extraction 141\u003c\/p\u003e \u003cp\u003eExperiment 4A Determination of Partition Coefficient for the System Benzoic Acid, Methylene Chloride, and Water 141\u003c\/p\u003e \u003cp\u003eDiscussion 141\u003c\/p\u003e \u003cp\u003eComponents 144\u003c\/p\u003e \u003cp\u003eExperimental Procedure 144\u003c\/p\u003e \u003cp\u003eExperiment 4B Solvent Extraction I: The System; Benzoic Acid, Methylene Chloride, and 10% Sodium Bicarbonate Solution; An Example of Acid–Base Extraction Techniques 146\u003c\/p\u003e \u003cp\u003eReaction 146\u003c\/p\u003e \u003cp\u003eDiscussion 146\u003c\/p\u003e \u003cp\u003eExperimental Procedure 146\u003c\/p\u003e \u003cp\u003eExperiment 4C Solvent Extraction II: A Three-Component Mixture; An Example of the Separation of an Acid, a Base, and a Neutral Substance 147\u003c\/p\u003e \u003cp\u003eDiscussion 147\u003c\/p\u003e \u003cp\u003eComponents 148\u003c\/p\u003e \u003cp\u003eExperimental Procedure 148\u003c\/p\u003e \u003cp\u003eEXPERIMENT 5 Reduction of Ketones Using a Metal Hydride Reagent: Cyclohexanol and cis- and trans-4-tert-Butylcyclohexanol 151\u003c\/p\u003e \u003cp\u003eReaction (Experiment [5A]) 151\u003c\/p\u003e \u003cp\u003eDiscussion 152\u003c\/p\u003e \u003cp\u003eExperiment 5A Cyclohexanol 153\u003c\/p\u003e \u003cp\u003eExperimental Procedure 153\u003c\/p\u003e \u003cp\u003eExperiment 5B cis- and trans-4-tert-Butylcyclohexanol 158\u003c\/p\u003e \u003cp\u003eReaction 158\u003c\/p\u003e \u003cp\u003eExperimental Procedure 158\u003c\/p\u003e \u003cp\u003eEXPERIMENT 6 Photochemical Isomerization of an Alkene: cis-1,2-Dibenzoylethylene 163\u003c\/p\u003e \u003cp\u003eBiologically Important Photochemical Reactions 164\u003c\/p\u003e \u003cp\u003eReaction 165\u003c\/p\u003e \u003cp\u003eDiscussion 166\u003c\/p\u003e \u003cp\u003eExperiment 6A Purification of trans-1,2-Dibenzoylethylene 166\u003c\/p\u003e \u003cp\u003eExperimental Procedure 166\u003c\/p\u003e \u003cp\u003eExperiment 6B Isomerization of an Alkene: Thin-Layer Chromatographic Analysis 167\u003c\/p\u003e \u003cp\u003eExperimental Procedure 167\u003c\/p\u003e \u003cp\u003eExperiment 6C Isomerization of an Alkene: Nuclear Magnetic Resonance Analysis 173\u003c\/p\u003e \u003cp\u003eExperimental Procedure 173\u003c\/p\u003e \u003cp\u003eEXPERIMENT 7 The Cannizzaro Reaction with 4-Chlorobenzaldehyde: 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol 174\u003c\/p\u003e \u003cp\u003eReaction 176\u003c\/p\u003e \u003cp\u003eDiscussion 176\u003c\/p\u003e \u003cp\u003eExperimental Procedure 177\u003c\/p\u003e \u003cp\u003eExperiment 7-1 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol: Preparation Using a Monomode Microwave Apparatus 184\u003c\/p\u003e \u003cp\u003eExperimental Procedure 184\u003c\/p\u003e \u003cp\u003eExperiment 7-2 4-Chlorobenzoic Acid and\u003c\/p\u003e \u003cp\u003e4-Chlorobenzyl Alcohol: Preparation Using a Multimode Microwave Apparatus 185\u003c\/p\u003e \u003cp\u003eExperimental Procedure 185\u003c\/p\u003e \u003cp\u003eEXPERIMENT 8 The Esterification Reaction: Ethyl Laurate, Isopentyl Acetate, and the Use of Acidic Resins 188\u003c\/p\u003e \u003cp\u003eReaction 188\u003c\/p\u003e \u003cp\u003eDiscussion 189\u003c\/p\u003e \u003cp\u003eLipids 190\u003c\/p\u003e \u003cp\u003eExperiment 8A Ethyl Laurate 199\u003c\/p\u003e \u003cp\u003eReaction 199\u003c\/p\u003e \u003cp\u003eExperimental Procedure 199\u003c\/p\u003e \u003cp\u003eExperiment 8B Isopentyl Acetate: Semimicroscale Preparation 201\u003c\/p\u003e \u003cp\u003eReaction 201\u003c\/p\u003e \u003cp\u003eExperimental Procedure 201\u003c\/p\u003e \u003cp\u003eExperiment 8B-1 Isopentyl Acetate: Preparation Using a Monomode Microwave Apparatus 203\u003c\/p\u003e \u003cp\u003eExperimental Procedure 203\u003c\/p\u003e \u003cp\u003eExperiment 8B-2 Isopentyl Acetate: Preparation Using a Multimode Microwave Apparatus 205\u003c\/p\u003e \u003cp\u003eExperimental Procedure 205\u003c\/p\u003e \u003cp\u003eExperiment 8C Esterification by Use of Acidic Resins: Semimicroscale Preparations 206\u003c\/p\u003e \u003cp\u003eReaction 207\u003c\/p\u003e \u003cp\u003eExperimental Procedure 207\u003c\/p\u003e \u003cp\u003eEXPERIMENT 9 The E1 Elimination Reaction: Dehydration of 2-Butanol to Yield 1-Butene, trans-2-Butene, and cis-2-Butene 209\u003c\/p\u003e \u003cp\u003eThe Development of Carbocation Theory 210\u003c\/p\u003e \u003cp\u003eReaction 211\u003c\/p\u003e \u003cp\u003eDiscussion 212\u003c\/p\u003e \u003cp\u003eExperimental Procedure 215\u003c\/p\u003e \u003cp\u003eEXPERIMENT 10 The E2 Elimination Reaction: Dehydrohalogenation of 2-Bromobutane to Yield 1-Butene, trans-2-Butene, and cis-2-Butene 217\u003c\/p\u003e \u003cp\u003eReaction 218\u003c\/p\u003e \u003cp\u003eDiscussion 218\u003c\/p\u003e \u003cp\u003eExperimental Procedure 220\u003c\/p\u003e \u003cp\u003eEXPERIMENT 11 The Isolation of Natural Products 224\u003c\/p\u003e \u003cp\u003eExperiment 11A Isolation and Characterization of an Optically Active Natural Product: Usnic Acid 224\u003c\/p\u003e \u003cp\u003eLichens and Natural Products 225\u003c\/p\u003e \u003cp\u003eDiscussion 227\u003c\/p\u003e \u003cp\u003eExperimental Procedure 227\u003c\/p\u003e \u003cp\u003eExperiment 11B Isolation and Characterization of a Natural Product: Caffeine and Caffeine 5-Nitrosalicylate 229\u003c\/p\u003e \u003cp\u003eAlkaloids 230\u003c\/p\u003e \u003cp\u003eThe Classification of Alkaloids 230\u003c\/p\u003e \u003cp\u003eDiscussion 231\u003c\/p\u003e \u003cp\u003eExperimental Procedure 233\u003c\/p\u003e \u003cp\u003eDerivative: Caffeine 5-Nitrosalicylate 235\u003c\/p\u003e \u003cp\u003eExperimental Procedure 236\u003c\/p\u003e \u003cp\u003eExperiment 11C Isolation of a Natural Product by Steam Distillation: Cinnamaldehyde from Cinnamon 238\u003c\/p\u003e \u003cp\u003eEssential Oils 239\u003c\/p\u003e \u003cp\u003eDiscussion 241\u003c\/p\u003e \u003cp\u003eComponent 242\u003c\/p\u003e \u003cp\u003eExperimental Procedure 242\u003c\/p\u003e \u003cp\u003eEXPERIMENT 12 Reductive Catalytic Hydrogenation of an Alkene: Octane 244\u003c\/p\u003e \u003cp\u003eReaction 245\u003c\/p\u003e \u003cp\u003eDiscussion 245\u003c\/p\u003e \u003cp\u003eExperimental Procedure 247\u003c\/p\u003e \u003cp\u003eEXPERIMENT 13 Hydroboration–Oxidation of an Alkene: Octanol 250\u003c\/p\u003e \u003cp\u003eReaction 251\u003c\/p\u003e \u003cp\u003eDiscussion 251\u003c\/p\u003e \u003cp\u003eExperimental Procedure 254\u003c\/p\u003e \u003cp\u003eEXPERIMENT 14 Diels–Alder Reaction: 4-Cyclohexenecis-1,2-dicarboxylic Acid Anhydride 257\u003c\/p\u003e \u003cp\u003eReaction 258\u003c\/p\u003e \u003cp\u003eDiscussion 259\u003c\/p\u003e \u003cp\u003eExperimental Procedure 261\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale Preparation 266\u003c\/p\u003e \u003cp\u003eEXPERIMENT 15 Diels–Alder Reaction: 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride 269\u003c\/p\u003e \u003cp\u003eReaction 269\u003c\/p\u003e \u003cp\u003eDiscussion 270\u003c\/p\u003e \u003cp\u003eExperimental Procedure 271\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale Preparations 272\u003c\/p\u003e \u003cp\u003eExperiment 15-1 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride: Preparation Using a Monomode Microwave Apparatus 273\u003c\/p\u003e \u003cp\u003eExperimental Procedure 273\u003c\/p\u003e \u003cp\u003eExperiment 15-2 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride: Preparation Using a Multimode Microwave Apparatus 274\u003c\/p\u003e \u003cp\u003eExperimental Procedure 274\u003c\/p\u003e \u003cp\u003eEXPERIMENT 16 Grignard Reaction with a Ketone: Triphenylmethanol 275\u003c\/p\u003e \u003cp\u003eReaction 276\u003c\/p\u003e \u003cp\u003eDiscussion 277\u003c\/p\u003e \u003cp\u003eExperimental Procedure 279\u003c\/p\u003e \u003cp\u003eEXPERIMENT 17 Grignard Reaction with an Aldehyde: 4-Methyl-3-heptanol 284\u003c\/p\u003e \u003cp\u003eReaction 284\u003c\/p\u003e \u003cp\u003eDiscussion 284\u003c\/p\u003e \u003cp\u003eExperimental Procedure 285\u003c\/p\u003e \u003cp\u003eEXPERIMENT 18 The Perkin Reaction: Condensation of Rhodanine with an Aromatic Aldehyde to Yield o-Chlorobenzylidene Rhodanine 289\u003c\/p\u003e \u003cp\u003eReaction 290\u003c\/p\u003e \u003cp\u003eDiscussion 291\u003c\/p\u003e \u003cp\u003eExperimental Procedure 292\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale Preparation 293\u003c\/p\u003e \u003cp\u003eEXPERIMENT 19 Alkene Preparation by the\u003c\/p\u003e \u003cp\u003eWittig Reaction: (E)-Stilbene; Methylene-4-tertbutylcyclohexane; and trans-9-(2-Phenylethenyl) anthracene 294\u003c\/p\u003e \u003cp\u003eReaction 296\u003c\/p\u003e \u003cp\u003eDiscussion 296\u003c\/p\u003e \u003cp\u003eExperiment 19A (E)-Stilbene by the “Instant Ylide” Method 299\u003c\/p\u003e \u003cp\u003eReaction 299\u003c\/p\u003e \u003cp\u003eExperimental Procedure 300\u003c\/p\u003e \u003cp\u003eExperiment 19B (E)-Stilbene by the Horner–Wadsworth–Emmons Reaction 302\u003c\/p\u003e \u003cp\u003eReaction 302\u003c\/p\u003e \u003cp\u003eExperimental Procedure 302\u003c\/p\u003e \u003cp\u003eExperiment 19C Methylene-4-tert-butylcyclohexane 303\u003c\/p\u003e \u003cp\u003eReaction 303\u003c\/p\u003e \u003cp\u003eExperimental Procedure 304\u003c\/p\u003e \u003cp\u003eExperiment 19D trans-9-(2-Phenylethenyl) anthracene 306\u003c\/p\u003e \u003cp\u003eReaction 306\u003c\/p\u003e \u003cp\u003eExperimental Procedure 306\u003c\/p\u003e \u003cp\u003eEXPERIMENT 20 Aldol Reaction: Dibenzalacetone 309\u003c\/p\u003e \u003cp\u003eReaction 309\u003c\/p\u003e \u003cp\u003eDiscussion 310\u003c\/p\u003e \u003cp\u003eExperimental Procedure 311\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale Preparation 316\u003c\/p\u003e \u003cp\u003eEXPERIMENT 21 Quantitative Analysis of Grignard Reagents: 1-Methylbutylmagnesium Bromide and Phenylmagnesium Bromide 317\u003c\/p\u003e \u003cp\u003eReaction 318\u003c\/p\u003e \u003cp\u003eDiscussion 318\u003c\/p\u003e \u003cp\u003eExperimental Procedure 319\u003c\/p\u003e \u003cp\u003eEXPERIMENT 22 Williamson Synthesis of Ethers 321\u003c\/p\u003e \u003cp\u003eReaction 321\u003c\/p\u003e \u003cp\u003eDiscussion 322\u003c\/p\u003e \u003cp\u003eExperiment 22A Propyl p-Tolyl Ether 323\u003c\/p\u003e \u003cp\u003eExperimental Procedure 323\u003c\/p\u003e \u003cp\u003eOptional Macroscale Preparation 324\u003c\/p\u003e \u003cp\u003eExperiment 22B Methyl p-Ethylphenyl Ether 327\u003c\/p\u003e \u003cp\u003eReaction 327\u003c\/p\u003e \u003cp\u003eExperimental Procedure 327\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale and Macroscale\u003c\/p\u003e \u003cp\u003ePreparations 329\u003c\/p\u003e \u003cp\u003eExperiment 22C Butyl p-Nitrophenyl Ether: Preparation Using a Monomode Microwave Apparatus 332\u003c\/p\u003e \u003cp\u003eReaction 332\u003c\/p\u003e \u003cp\u003eExperimental Procedure 332\u003c\/p\u003e \u003cp\u003eExperiment 22D Butyl p-Nitrophenyl Ether: Preparation Using a Multimode Microwave Apparatus 334\u003c\/p\u003e \u003cp\u003eReaction 334\u003c\/p\u003e \u003cp\u003eExperimental Procedure 334\u003c\/p\u003e \u003cp\u003eEXPERIMENT 23 Amide Synthesis: Acetanilide and N,N’-Diacetyl-1,4-phenylenediamine 338\u003c\/p\u003e \u003cp\u003eReaction 338\u003c\/p\u003e \u003cp\u003eDiscussion 339\u003c\/p\u003e \u003cp\u003eExperiment 23A Acetanilide 341\u003c\/p\u003e \u003cp\u003eExperimental Procedure 341\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale Preparation 342\u003c\/p\u003e \u003cp\u003eExperiment 23B N,N’-Diacetyl-1,4-phenylenediamine 343\u003c\/p\u003e \u003cp\u003eReaction 343\u003c\/p\u003e \u003cp\u003eExperimental Procedure 343\u003c\/p\u003e \u003cp\u003eEXPERIMENT 24 Imide Synthesis: N-Phenylmaleimide 346\u003c\/p\u003e \u003cp\u003eReaction 346\u003c\/p\u003e \u003cp\u003eDiscussion 347\u003c\/p\u003e \u003cp\u003eExperiment 24A Maleanilic Acid 348\u003c\/p\u003e \u003cp\u003eExperimental Procedure 348\u003c\/p\u003e \u003cp\u003eReaction 348\u003c\/p\u003e \u003cp\u003eExperiment 24B N-Phenylmaleimide 349\u003c\/p\u003e \u003cp\u003eReaction 349\u003c\/p\u003e \u003cp\u003eExperimental Procedure 350\u003c\/p\u003e \u003cp\u003eEXPERIMENT 25 Synthesis of Cyclic Carboxylic Acid Anhydrides: Succinic Anhydride and Phthalic Anhydride 352\u003c\/p\u003e \u003cp\u003eReaction 352\u003c\/p\u003e \u003cp\u003eDiscussion 352\u003c\/p\u003e \u003cp\u003eExperiment 25A Succinic Anhydride 354\u003c\/p\u003e \u003cp\u003eExperimental Procedure 354\u003c\/p\u003e \u003cp\u003eExperiment 25B Phthalic Anhydride 355\u003c\/p\u003e \u003cp\u003eReaction 355\u003c\/p\u003e \u003cp\u003eExperimental Procedure 355\u003c\/p\u003e \u003cp\u003eEXPERIMENT 26 Diazonium Coupling Reaction: Methyl Red 356\u003c\/p\u003e \u003cp\u003eReaction 357\u003c\/p\u003e \u003cp\u003eDiscussion 357\u003c\/p\u003e \u003cp\u003eExperimental Procedure 359\u003c\/p\u003e \u003cp\u003eEXPERIMENT 27 Friedel–Crafts Acylation: Acetylferrocene and Diacetylferrocene 361\u003c\/p\u003e \u003cp\u003eReaction 362\u003c\/p\u003e \u003cp\u003eDiscussion 362\u003c\/p\u003e \u003cp\u003eExperimental Procedure 364\u003c\/p\u003e \u003cp\u003eEXPERIMENT 28 Halogenation: Electrophilic Aromatic Substitution to Yield 4-Bromoacetanilide 368\u003c\/p\u003e \u003cp\u003eReaction 368\u003c\/p\u003e \u003cp\u003eDiscussion 369\u003c\/p\u003e \u003cp\u003eExperimental Procedure 369\u003c\/p\u003e \u003cp\u003eEXPERIMENT 29 Nitration: 2,5-Dichloronitrobenzene; N,N’-Diacetyl-2,3-dinitro-1,4-phenylenediamine; 5-Nitrosalicylic Acid; and 2- and 4-Nitrophenol 373\u003c\/p\u003e \u003cp\u003eGeneral Reaction 374\u003c\/p\u003e \u003cp\u003eDiscussion 374\u003c\/p\u003e \u003cp\u003eSemimicroscale Preparation of Anhydrous Nitric Acid 375\u003c\/p\u003e \u003cp\u003eExperimental Procedure 376\u003c\/p\u003e \u003cp\u003eExperiment 29A 2,5-Dichloronitrobenzene 376\u003c\/p\u003e \u003cp\u003eReaction 376\u003c\/p\u003e \u003cp\u003eExperimental Procedure 377\u003c\/p\u003e \u003cp\u003eExperiment 29B N,N-Diacetyl-2,3-dinitro-1,4-phenylenediamine 378\u003c\/p\u003e \u003cp\u003eReaction 378\u003c\/p\u003e \u003cp\u003eExperimental Procedure 378\u003c\/p\u003e \u003cp\u003eExperiment 29C 5-Nitrosalicylic Acid 379\u003c\/p\u003e \u003cp\u003eReaction 379\u003c\/p\u003e \u003cp\u003eExperimental Procedure 380\u003c\/p\u003e \u003cp\u003eExperiment 29D 2- and 4-Nitrophenol 381\u003c\/p\u003e \u003cp\u003eReaction 381\u003c\/p\u003e \u003cp\u003eExperimental Procedure 381\u003c\/p\u003e \u003cp\u003eEXPERIMENT 30 Nucleophilic Aromatic Substitution: 2,4-Dinitrophenylthiocyanate 384\u003c\/p\u003e \u003cp\u003eReaction 385\u003c\/p\u003e \u003cp\u003eDiscussion 385\u003c\/p\u003e \u003cp\u003eExperimental Procedure 386\u003c\/p\u003e \u003cp\u003eExperiment 30-1 2,4-Dinitrophenylthiocyanate: Preparation Using a Monomode Microwave Apparatus 387\u003c\/p\u003e \u003cp\u003eExperimental Procedure 387\u003c\/p\u003e \u003cp\u003eExperiment 30-2 2,4-Dinitrophenylthiocyanate: Preparation Using a Multimode Microwave Apparatus 388\u003c\/p\u003e \u003cp\u003eExperimental Procedure 388\u003c\/p\u003e \u003cp\u003eEXPERIMENT 31 Halogenation Using\u003c\/p\u003e \u003cp\u003eN-Bromosuccinimide: 9-Bromoanthracene 390\u003c\/p\u003e \u003cp\u003eReaction 390\u003c\/p\u003e \u003cp\u003eDiscussion 391\u003c\/p\u003e \u003cp\u003eInitiation Step 391\u003c\/p\u003e \u003cp\u003ePropagation Step 391\u003c\/p\u003e \u003cp\u003eExperimental Procedure 392\u003c\/p\u003e \u003cp\u003eEXPERIMENT 32 Hypochlorite Oxidation of an Alcohol: Cyclohexanone 394\u003c\/p\u003e \u003cp\u003eReaction 394\u003c\/p\u003e \u003cp\u003eDiscussion 394\u003c\/p\u003e \u003cp\u003eExperimental Procedure 395\u003c\/p\u003e \u003cp\u003eEXPERIMENT 33 Chromium Trioxide–Resin or Hypochlorite Oxidation of an Alcohol: 9-Fluorenone 398\u003c\/p\u003e \u003cp\u003eExperiment 33A 9-Fluorenone: CrO3 Oxidation of 9-Fluorenol 398\u003c\/p\u003e \u003cp\u003eReaction 398\u003c\/p\u003e \u003cp\u003eDiscussion 398\u003c\/p\u003e \u003cp\u003eExperimental Procedure 399\u003c\/p\u003e \u003cp\u003eExperiment 33B 9-Fluorenone: NaOCl Oxidation of 9-Fluorenol 401\u003c\/p\u003e \u003cp\u003eReaction 401\u003c\/p\u003e \u003cp\u003eDiscussion 401\u003c\/p\u003e \u003cp\u003eExperimental Procedure 401\u003c\/p\u003e \u003cp\u003eEXPERIMENT 34 Hypochlorite Oxidation of Methyl Ketones by the Haloform Reaction: Benzoic Acid and p-Methoxybenzoic Acid 403\u003c\/p\u003e \u003cp\u003eReaction 404\u003c\/p\u003e \u003cp\u003eDiscussion 404\u003c\/p\u003e \u003cp\u003eExperiment 34A Benzoic Acid 405\u003c\/p\u003e \u003cp\u003eExperimental Procedure 405\u003c\/p\u003e \u003cp\u003eExperiment 34B p-Methoxybenzoic Acid 406\u003c\/p\u003e \u003cp\u003eReaction 406\u003c\/p\u003e \u003cp\u003eExperimental Procedure 406\u003c\/p\u003e \u003cp\u003eOptional Semimicroscale Preparation 407\u003c\/p\u003e \u003cp\u003eEXPERIMENT 35 Conversion of Cyclohexyl Bromide to Cyclohexene–An E2 Elimination Reaction: Factors Affecting the Rate of a Chemical\u003c\/p\u003e \u003cp\u003eReaction 409\u003c\/p\u003e \u003cp\u003eReaction 409\u003c\/p\u003e \u003cp\u003eDiscussion 409\u003c\/p\u003e \u003cp\u003eExperimental Procedure 414\u003c\/p\u003e \u003cp\u003eData Analysis 416\u003c\/p\u003e \u003cp\u003eVariation of Parameters 416\u003c\/p\u003e \u003cp\u003eEXPERIMENT 36 Aqueous Suzuki Synthesis of 4-Phenylphenol 421\u003c\/p\u003e \u003cp\u003eReaction 421\u003c\/p\u003e \u003cp\u003eDiscussion 421\u003c\/p\u003e \u003cp\u003eExperimental Procedure 424\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 7 SEQUENTIAL SYNTHESES: THE TRANSITION FROM MACRO TO MICRO 428\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eSEQUENCE A The Synthesis of Hexaphenylbenzene 431\u003c\/p\u003e \u003cp\u003eEXPERIMENTS A1a, A2a, A3a, A1b, A2b, A3b, and A4ab The Synthesis of Hexaphenylbenzene from Benzaldehyde: 434\u003c\/p\u003e \u003cp\u003eExperiment A1a The Benzoin Condensation of Benzaldehyde: Benzoin 436\u003c\/p\u003e \u003cp\u003eReaction 436\u003c\/p\u003e \u003cp\u003eDiscussion 437\u003c\/p\u003e \u003cp\u003eSemimicroscale Experimental Procedure 438\u003c\/p\u003e \u003cp\u003eOptional Scales 439\u003c\/p\u003e \u003cp\u003eMicroscale Reaction Procedure 439\u003c\/p\u003e \u003cp\u003eExperiment A2a Copper(II) Ion Oxidation of Benzoin: Benzil 440\u003c\/p\u003e \u003cp\u003eReaction 441\u003c\/p\u003e \u003cp\u003eDiscussion 441\u003c\/p\u003e \u003cp\u003eSemimicroscale Experimental Procedure 442\u003c\/p\u003e \u003cp\u003eOptional Microscale Preparation 444\u003c\/p\u003e \u003cp\u003eExperiment A3a Tetraphenylcyclopentadienone 445\u003c\/p\u003e \u003cp\u003eReaction 445\u003c\/p\u003e \u003cp\u003eDiscussion 446\u003c\/p\u003e \u003cp\u003eMicroscale Reaction Procedure (1) 446\u003c\/p\u003e \u003cp\u003eMicroscale Reaction Procedure (2) 447\u003c\/p\u003e \u003cp\u003eExperiment A1b (E)-Stilbene 448\u003c\/p\u003e \u003cp\u003eReaction 449\u003c\/p\u003e \u003cp\u003eDiscussion 449\u003c\/p\u003e \u003cp\u003eExperimental Procedure 450\u003c\/p\u003e \u003cp\u003eExperiment A2b Bromination of (E)-Stilbene: meso-Stilbene Dibromide 451\u003c\/p\u003e \u003cp\u003eReaction 452\u003c\/p\u003e \u003cp\u003eDiscussion 452\u003c\/p\u003e \u003cp\u003eSemimicroscale Experimental Procedure 454\u003c\/p\u003e \u003cp\u003eExperiment A3b Dehydrohalogenation of\u003c\/p\u003e \u003cp\u003emeso-Stilbene Dibromide: Diphenylacetylene 457\u003c\/p\u003e \u003cp\u003eReaction 457\u003c\/p\u003e \u003cp\u003eDiscussion 457\u003c\/p\u003e \u003cp\u003eSemimicroscale Experimental Procedure 458\u003c\/p\u003e \u003cp\u003eOptional Macroscale and Microscale\u003c\/p\u003e \u003cp\u003ePreparations 459\u003c\/p\u003e \u003cp\u003eExperiment A4ab Hexaphenylbenzene 460\u003c\/p\u003e \u003cp\u003eReaction 461\u003c\/p\u003e \u003cp\u003eDiscussion 461\u003c\/p\u003e \u003cp\u003eExperimental Procedure 462\u003c\/p\u003e \u003cp\u003eSEQUENCE B The Stepwise Synthesis of Nylon-6,6 464\u003c\/p\u003e \u003cp\u003eExperiment B1 Oxidation of Cyclohexanol: Adipic Acid 465\u003c\/p\u003e \u003cp\u003eReaction 465\u003c\/p\u003e \u003cp\u003eDiscussion 465\u003c\/p\u003e \u003cp\u003eExperimental Procedure 467\u003c\/p\u003e \u003cp\u003eExperiment B2 Preparation of an Acid Chloride: Adipoyl Chloride 468\u003c\/p\u003e \u003cp\u003eReaction 468\u003c\/p\u003e \u003cp\u003eDiscussion 469\u003c\/p\u003e \u003cp\u003eExperimental Procedure 469\u003c\/p\u003e \u003cp\u003eExperiment B3 Preparation of a Polyamide: Nylon-6,6 471\u003c\/p\u003e \u003cp\u003eReaction 471\u003c\/p\u003e \u003cp\u003eDiscussion 471\u003c\/p\u003e \u003cp\u003eExperimental Procedure 472\u003c\/p\u003e \u003cp\u003eSEQUENCE C The Synthesis of Sulfanilamide 473\u003c\/p\u003e \u003cp\u003eThe Sulfa Drugs 473\u003c\/p\u003e \u003cp\u003eExperiment C1 Acetylation of Aniline: 2,2,2-Trifluoroacetanilide 474\u003c\/p\u003e \u003cp\u003eReaction 475\u003c\/p\u003e \u003cp\u003eDiscussion 475\u003c\/p\u003e \u003cp\u003eExperimental Procedure 476\u003c\/p\u003e \u003cp\u003eExperiment C2 Chlorosulfonation of 2,2,2-\u003c\/p\u003e \u003cp\u003eTrifluoroacetanilide: p-(Trifluoroacetamido) benzenesulfonyl Chloride 477\u003c\/p\u003e \u003cp\u003eReaction 478\u003c\/p\u003e \u003cp\u003eDiscussion 478\u003c\/p\u003e \u003cp\u003eExperimental Procedure 479\u003c\/p\u003e \u003cp\u003eExperiment C3 Preparation of an Arene Sulfonamide: Sulfanilamide 480\u003c\/p\u003e \u003cp\u003eDiscussion 481\u003c\/p\u003e \u003cp\u003eExperimental Procedure 481\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 8 SPECTROSCOPIC IDENTIFICATION OF ORGANIC COMPOUNDS 484\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eInfrared Spectroscopy 484\u003c\/p\u003e \u003cp\u003eIntroduction to Group Frequencies: Interpretation of Infrared Spectra 485\u003c\/p\u003e \u003cp\u003eA Survey of Group Frequencies Identified in Organic Molecules 488\u003c\/p\u003e \u003cp\u003eGroup Frequencies of the Hydrocarbons 489\u003c\/p\u003e \u003cp\u003eGroup Frequencies of Carbonyl\u003c\/p\u003e \u003cp\u003eGroups: C O 490\u003c\/p\u003e \u003cp\u003eGroup Frequencies of the Heteroatom Functional Groups 492\u003c\/p\u003e \u003cp\u003eEsters 493\u003c\/p\u003e \u003cp\u003eInfrared Spectroscopy Instrumentation and Sample Handling 496\u003c\/p\u003e \u003cp\u003eInstrumentation 496\u003c\/p\u003e \u003cp\u003eSample Handling in the Infrared 497\u003c\/p\u003e \u003cp\u003eNuclear Magnetic Resonance Spectroscopy 504\u003c\/p\u003e \u003cp\u003eNuclear spin 504\u003c\/p\u003e \u003cp\u003eInstrumentation 505\u003c\/p\u003e \u003cp\u003eChemical Shift 508\u003c\/p\u003e \u003cp\u003eSpin–Spin Coupling 509\u003c\/p\u003e \u003cp\u003eIntensities 512\u003c\/p\u003e \u003cp\u003eSecond-Order Effects 513\u003c\/p\u003e \u003cp\u003eInterpretation of 1H NMR Spectra 514\u003c\/p\u003e \u003cp\u003e1H Chemical Shifts 517\u003c\/p\u003e \u003cp\u003eSpin–Spin Coupling 518\u003c\/p\u003e \u003cp\u003eGeminal Coupling 518\u003c\/p\u003e \u003cp\u003eVicinal Coupling 518\u003c\/p\u003e \u003cp\u003eLong-Range Coupling 520\u003c\/p\u003e \u003cp\u003eExamples of Complex, Yet First-Order, Coupling 520\u003c\/p\u003e \u003cp\u003eEthyl Vinyl Ether 520\u003c\/p\u003e \u003cp\u003eAllyl Acetate 522\u003c\/p\u003e \u003cp\u003e13C NMR Spectroscopy 525\u003c\/p\u003e \u003cp\u003eTwo-Dimensional NMR Spectroscopy 531\u003c\/p\u003e \u003cp\u003eNuclear Magnetic Resonance Sampling 532\u003c\/p\u003e \u003cp\u003eUltraviolet–Visible Spectroscopy: Introduction to Absorption Spectroscopy 537\u003c\/p\u003e \u003cp\u003eUV–VIS Spectroscopy 539\u003c\/p\u003e \u003cp\u003eApplication to Organic Molecules 540\u003c\/p\u003e \u003cp\u003eInstrumentation 547\u003c\/p\u003e \u003cp\u003eThe Source of Radiation 548\u003c\/p\u003e \u003cp\u003eThe Monochromator 549\u003c\/p\u003e \u003cp\u003eSample Compartment 550\u003c\/p\u003e \u003cp\u003eThe Detector 550\u003c\/p\u003e \u003cp\u003eThe Electronics: The Amplifier and Recorder 550\u003c\/p\u003e \u003cp\u003eSample Preparation 551\u003c\/p\u003e \u003cp\u003eCriteria for Choosing a Solvent 552\u003c\/p\u003e \u003cp\u003eMass Spectrometry 553\u003c\/p\u003e \u003cp\u003eInstrumentation 555\u003c\/p\u003e \u003cp\u003eIon Source 556\u003c\/p\u003e \u003cp\u003eMass Analyzer 557\u003c\/p\u003e \u003cp\u003eDetector 559\u003c\/p\u003e \u003cp\u003eTuning the Mass Spectrometer 559\u003c\/p\u003e \u003cp\u003eSample Introduction 560\u003c\/p\u003e \u003cp\u003eGas Chromatography\/Mass Spectrometry (GC\/MS) 560\u003c\/p\u003e \u003cp\u003eCapillary Columns 560\u003c\/p\u003e \u003cp\u003eSplit Injection 561\u003c\/p\u003e \u003cp\u003eSplit\/Splitless Injection 561\u003c\/p\u003e \u003cp\u003eFeatures of the Mass Spectrum 562\u003c\/p\u003e \u003cp\u003eTerms 563\u003c\/p\u003e \u003cp\u003eIsotope Peaks 563\u003c\/p\u003e \u003cp\u003eRecognizing the Molecular Ion 565\u003c\/p\u003e \u003cp\u003eMass Spectral Interpretation 566\u003c\/p\u003e \u003cp\u003eCase Study: Synthesis of Methyl Benzoate 567\u003c\/p\u003e \u003cp\u003e\u003cb\u003eChapter 9 QUALITATIVE IDENTIFICATION OF ORGANIC COMPOUNDS 573\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eOrganic Qualitative Analysis 573\u003c\/p\u003e \u003cp\u003ePreliminary Tests 575\u003c\/p\u003e \u003cp\u003eNonchemical Tests 575\u003c\/p\u003e \u003cp\u003eIgnition Test 576\u003c\/p\u003e \u003cp\u003eSeparation of Impurities 577\u003c\/p\u003e \u003cp\u003eDetection of Elements Other Than Carbon, Hydrogen, or Oxygen 578\u003c\/p\u003e \u003cp\u003eSodium Fusion 578\u003c\/p\u003e \u003cp\u003eSulfur 579\u003c\/p\u003e \u003cp\u003eNitrogen 580\u003c\/p\u003e \u003cp\u003eThe Halogens (Except Fluorine) 580\u003c\/p\u003e \u003cp\u003eSolubility Characteristics 582\u003c\/p\u003e \u003cp\u003eThe Classification Tests 584\u003c\/p\u003e \u003cp\u003eAlcohols 584\u003c\/p\u003e \u003cp\u003ePeriodic Acid: Vicinal Diols 586\u003c\/p\u003e \u003cp\u003eAldehydes and Ketones 586\u003c\/p\u003e \u003cp\u003eAlkanes and Cycloalkanes: Saturated Hydrocarbons 588\u003c\/p\u003e \u003cp\u003eAlkenes and Alkynes: Unsaturated Hydrocarbons 589\u003c\/p\u003e \u003cp\u003eAlkyl Halides 589\u003c\/p\u003e \u003cp\u003eAmides, Ammonium Salts, and Nitriles 591\u003c\/p\u003e \u003cp\u003eAmines 592\u003c\/p\u003e \u003cp\u003eAromatic Hydrocarbons with no Functional Groups 593\u003c\/p\u003e \u003cp\u003eCarboxylic Acids 594\u003c\/p\u003e \u003cp\u003eEsters 594\u003c\/p\u003e \u003cp\u003eEthers 595\u003c\/p\u003e \u003cp\u003eMethyl Ketones and Methyl Carbinols 595\u003c\/p\u003e \u003cp\u003eNitro Compounds 596\u003c\/p\u003e \u003cp\u003ePhenols and Enols 597\u003c\/p\u003e \u003cp\u003ePreparation of Derivatives 598\u003c\/p\u003e \u003cp\u003eCarboxylic Acids 599\u003c\/p\u003e \u003cp\u003ePreparation of Acid Chlorides 599\u003c\/p\u003e \u003cp\u003eAmides 599\u003c\/p\u003e \u003cp\u003eAnilides 600\u003c\/p\u003e \u003cp\u003eToluidides 600\u003c\/p\u003e \u003cp\u003eAlcohols 600\u003c\/p\u003e \u003cp\u003ePhenyl- and -Naphthylurethanes (Phenyl- and -Naphthylcarbamates) 600\u003c\/p\u003e \u003cp\u003e3,5-Dinitrobenzoates 601\u003c\/p\u003e \u003cp\u003eAldehydes and Ketones 602\u003c\/p\u003e \u003cp\u003e2,4-Dinitrophenylhydrazones 602\u003c\/p\u003e \u003cp\u003eSemicarbazones 602\u003c\/p\u003e \u003cp\u003eAmines 602\u003c\/p\u003e \u003cp\u003ePrimary and Secondary Amines: Acetamides 602\u003c\/p\u003e \u003cp\u003ePrimary and Secondary Amines: Benzamides 603\u003c\/p\u003e \u003cp\u003ePrimary, Secondary, and Tertiary Amines: Picrates 603\u003c\/p\u003e \u003cp\u003eAcid Chlorides and Anhydrides 604\u003c\/p\u003e \u003cp\u003eAmides 604\u003c\/p\u003e \u003cp\u003eAromatic Hydrocarbons 604\u003c\/p\u003e \u003cp\u003ePicrates 604\u003c\/p\u003e \u003cp\u003eNitriles 604\u003c\/p\u003e \u003cp\u003eHydrolysis to Amides 604\u003c\/p\u003e \u003cp\u003ePhenols 605\u003c\/p\u003e \u003cp\u003e-Naphthylurethanes (-Naphthylcarbamates) 605\u003c\/p\u003e \u003cp\u003eBromo Derivatives 605\u003c\/p\u003e \u003cp\u003eAliphatic Hydrocarbons, Halogenated Hydrocarbons, Amides, Nitro Compounds, Ethers, and Esters 606\u003c\/p\u003e \u003cp\u003eGlossary 609\u003c\/p\u003e \u003cp\u003eIndex 612\u003c\/p\u003e","brand":"John Wiley \u0026 Sons Inc","offers":[{"title":"Default Title","offer_id":49528821219671,"sku":"9781118083406","price":170.0,"currency_code":"GBP","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0817\/1739\/5799\/files\/9781118083406.jpg?v=1731873148","url":"https:\/\/bookcurl.com\/products\/microscale-organic-laboratory-with-multistep-and-multiscale-syntheses-6e-9781118083406","provider":"Book Curl","version":"1.0","type":"link"}