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Microscale Organic Laboratory with Multistep and Multiscale Syntheses, Binder Ready Version
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Chapter 1 INTRODUCTION 1 General Rules for the Microscale Laboratory 3 The Organic Chemistry Laboratory 4 Chapter 2 SAFETY 5 Making the Laboratory a Safer Place 5 Nature of Hazards 5 Reduction of Risks 6 Precautionary Measures 7 Thinking About the Risks In Using Chemicals 8 Disposal of Chemicals 8 Material Safety Data Sheets 9 Alternate Sources of Information 12 Estimating Risks from Vapors 13 Microwave Safety 14 Concluding Thoughts 15 General Safety References 16 Chapter 3 INTRODUCTION TO MICROSCALE ORGANIC LABORATORY EQUIPMENT AND TECHNIQUES 18 Microglassware Equipment 19 Standard Taper Joints 19 Conical Vials 20 Condensers 20 Distillation Heads 20 Recrystallization Tubes 20 Miscellaneous Items 20 Gas Chromatographic Fraction Collection Items 21 Standard Experimental Apparatus 21 Heating and Stirring Arrangements 21 Sand Bath Technique?Hot Plate Calibration 21 Metal Heat-Transfer Devices 22 Stirring 22 Reflux Apparatus 23 Distillation Apparatus 24 Moisture-Protected Reaction Apparatus 25 Specialized Pieces of Equipment 26 Microwave Heating as a Tool for Organic Chemistry 27 Introduction 27 Applications 32 Equipment Available 34 Experimental Protocols 35 Microscale Laws 35 Rules of the Trade for Handling Organic Materials at the Microscale Level 35 Rules for Working with Liquids at the Microscale Level 36 Rules for Working with Solids at the Microscale Level 39 The Laboratory Notebook 40 Example of a Laboratory Notebook Entry 41 Calculating Yields 42 Chapter 4 DETERMINATION OF PHYSICAL PROPERTIES 45 Liquids 46 Ultramicro Boiling Point 46 Density 50 Solids 51 Melting Points 51 Chapter 5 MICROSCALE LABORATORY TECHNIQUES 55 TECHNIQUE 1 Gas Chromatography 55 GC Instrumentation 56 TECHNIQUE 2 Simple Distillation 61 TECHNIQUE 3 Fractional Distillation 64 TECHNIQUE 4 Solvent Extraction 67 Intermolecular Properties: Solubility 67 Partition (or Distribution) Coefficient 70 Extraction 72 Solid?Liquid Extraction 79 Drying Agents 80 Solid-Phase Extraction 83 TECHNIQUE 5 Crystallization 85 General Crystallization Procedure 85 Simple Crystallization 87 Filtration Techniques 88 TECHNIQUE 6 Chromatography 92 Column, Flash, High-Performance Liquid, and Thin-Layer Chromatography 92 Column Chromatography 92 Flash Chromatography 95 Thin-Layer Chromatography 97 Paper Chromatography 99 High-Performance Liquid Chromatography 100 TECHNIQUE 6B Concentration of Solutions 101 Distillation 102 Evaporation with Nitrogen Gas 102 Removal of Solvent Under Reduced Pressure 102 TECHNIQUE 7 Collection or Control of Gaseous Products 105 Water-Insoluble Gases 105 Trapping Byproduct Gases 106 TECHNIQUE 8 Measurement of Specific Rotation 108 Theory 108 The Polarimeter 109 TECHNIQUE 9 Sublimation 111 Sublimation Theory 112 Experimental Setup 113 Precautions 113 Chapter 6 MICROSCALE ORGANIC LABORATORY EXPERIMENTS 115 EXPERIMENT 1 Getting to Know You: Measurement of Physical Properties 116 Discussion 117 Experimental Procedure 118 Melting Point 118 EXPERIMENT 2 The Separation of a 25-L Mixture of Heptanal (bp 153 C) and Cyclohexanol (bp 160 C) by Gas Chromatography 123 Discussion 123 Collection Yield 124 Collection Yield 125 Components 126 Experimental Procedure 126 EXPERIMENT 3 Distillation 129 Experiment 3A Simple Distillation at the Semimicroscale Level: Separation of Ethyl Acetate from trans-1,2-Dibenzoylethylene 130 Discussion 130 Components 130 Experimental Procedure 131 Experiment 3B Fractional Semimicroscale Distillation: Separation of Hexane and Toluene 132 Discussion 133 Components 133 Experimental Procedure 133 Experiment 3C Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning-Band Column 135 Discussion 135 Components 136 Experimental Procedure 136 Experiment 3D Fractional Semimicroscale Distillation: The Separation of 2-Methylpentane and Cyclohexane Using a Spinning Band in a Hickman?Hinkle Still 138 Discussion 139 Components 139 Experimental Procedure 139 EXPERIMENT 4 Solvent Extraction 141 Experiment 4A Determination of Partition Coefficient for the System Benzoic Acid, Methylene Chloride, and Water 141 Discussion 141 Components 144 Experimental Procedure 144 Experiment 4B Solvent Extraction I: The System; Benzoic Acid, Methylene Chloride, and 10% Sodium Bicarbonate Solution; An Example of Acid?Base Extraction Techniques 146 Reaction 146 Discussion 146 Experimental Procedure 146 Experiment 4C Solvent Extraction II: A Three-Component Mixture; An Example of the Separation of an Acid, a Base, and a Neutral Substance 147 Discussion 147 Components 148 Experimental Procedure 148 EXPERIMENT 5 Reduction of Ketones Using a Metal Hydride Reagent: Cyclohexanol and cis- and trans-4-tert-Butylcyclohexanol 151 Reaction (Experiment [5A]) 151 Discussion 152 Experiment 5A Cyclohexanol 153 Experimental Procedure 153 Experiment 5B cis- and trans-4-tert-Butylcyclohexanol 158 Reaction 158 Experimental Procedure 158 EXPERIMENT 6 Photochemical Isomerization of an Alkene: cis-1,2-Dibenzoylethylene 163 Biologically Important Photochemical Reactions 164 Reaction 165 Discussion 166 Experiment 6A Purification of trans-1,2-Dibenzoylethylene 166 Experimental Procedure 166 Experiment 6B Isomerization of an Alkene: Thin-Layer Chromatographic Analysis 167 Experimental Procedure 167 Experiment 6C Isomerization of an Alkene: Nuclear Magnetic Resonance Analysis 173 Experimental Procedure 173 EXPERIMENT 7 The Cannizzaro Reaction with 4-Chlorobenzaldehyde: 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol 174 Reaction 176 Discussion 176 Experimental Procedure 177 Experiment 7-1 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol: Preparation Using a Monomode Microwave Apparatus 184 Experimental Procedure 184 Experiment 7-2 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol: Preparation Using a Multimode Microwave Apparatus 185 Experimental Procedure 185 EXPERIMENT 8 The Esterification Reaction: Ethyl Laurate, Isopentyl Acetate, and the Use of Acidic Resins 188 Reaction 188 Discussion 189 Lipids 190 Experiment 8A Ethyl Laurate 199 Reaction 199 Experimental Procedure 199 Experiment 8B Isopentyl Acetate: Semimicroscale Preparation 201 Reaction 201 Experimental Procedure 201 Experiment 8B-1 Isopentyl Acetate: Preparation Using a Monomode Microwave Apparatus 203 Experimental Procedure 203 Experiment 8B-2 Isopentyl Acetate: Preparation Using a Multimode Microwave Apparatus 205 Experimental Procedure 205 Experiment 8C Esterification by Use of Acidic Resins: Semimicroscale Preparations 206 Reaction 207 Experimental Procedure 207 EXPERIMENT 9 The E1 Elimination Reaction: Dehydration of 2-Butanol to Yield 1-Butene, trans-2-Butene, and cis-2-Butene 209 The Development of Carbocation Theory 210 Reaction 211 Discussion 212 Experimental Procedure 215 EXPERIMENT 10 The E2 Elimination Reaction: Dehydrohalogenation of 2-Bromobutane to Yield 1-Butene, trans-2-Butene, and cis-2-Butene 217 Reaction 218 Discussion 218 Experimental Procedure 220 EXPERIMENT 11 The Isolation of Natural Products 224 Experiment 11A Isolation and Characterization of an Optically Active Natural Product: Usnic Acid 224 Lichens and Natural Products 225 Discussion 227 Experimental Procedure 227 Experiment 11B Isolation and Characterization of a Natural Product: Caffeine and Caffeine 5-Nitrosalicylate 229 Alkaloids 230 The Classification of Alkaloids 230 Discussion 231 Experimental Procedure 233 Derivative: Caffeine 5-Nitrosalicylate 235 Experimental Procedure 236 Experiment 11C Isolation of a Natural Product by Steam Distillation: Cinnamaldehyde from Cinnamon 238 Essential Oils 239 Discussion 241 Component 242 Experimental Procedure 242 EXPERIMENT 12 Reductive Catalytic Hydrogenation of an Alkene: Octane 244 Reaction 245 Discussion 245 Experimental Procedure 247 EXPERIMENT 13 Hydroboration?Oxidation of an Alkene: Octanol 250 Reaction 251 Discussion 251 Experimental Procedure 254 EXPERIMENT 14 Diels?Alder Reaction: 4-Cyclohexenecis-1,2-dicarboxylic Acid Anhydride 257 Reaction 258 Discussion 259 Experimental Procedure 261 Optional Semimicroscale Preparation 266 EXPERIMENT 15 Diels?Alder Reaction: 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride 269 Reaction 269 Discussion 270 Experimental Procedure 271 Optional Semimicroscale Preparations 272 Experiment 15-1 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride: Preparation Using a Monomode Microwave Apparatus 273 Experimental Procedure 273 Experiment 15-2 9,10-Dihydroanthracene-9,10-,-succinic Acid Anhydride: Preparation Using a Multimode Microwave Apparatus 274 Experimental Procedure 274 EXPERIMENT 16 Grignard Reaction with a Ketone: Triphenylmethanol 275 Reaction 276 Discussion 277 Experimental Procedure 279 EXPERIMENT 17 Grignard Reaction with an Aldehyde: 4-Methyl-3-heptanol 284 Reaction 284 Discussion 284 Experimental Procedure 285 EXPERIMENT 18 The Perkin Reaction: Condensation of Rhodanine with an Aromatic Aldehyde to Yield o-Chlorobenzylidene Rhodanine 289 Reaction 290 Discussion 291 Experimental Procedure 292 Optional Semimicroscale Preparation 293 EXPERIMENT 19 Alkene Preparation by the Wittig Reaction: (E)-Stilbene; Methylene-4-tertbutylcyclohexane; and trans-9-(2-Phenylethenyl) anthracene 294 Reaction 296 Discussion 296 Experiment 19A (E)-Stilbene by the ?Instant Ylide? Method 299 Reaction 299 Experimental Procedure 300 Experiment 19B (E)-Stilbene by the Horner?Wadsworth?Emmons Reaction 302 Reaction 302 Experimental Procedure 302 Experiment 19C Methylene-4-tert-butylcyclohexane 303 Reaction 303 Experimental Procedure 304 Experiment 19D trans-9-(2-Phenylethenyl) anthracene 306 Reaction 306 Experimental Procedure 306 EXPERIMENT 20 Aldol Reaction: Dibenzalacetone 309 Reaction 309 Discussion 310 Experimental Procedure 311 Optional Semimicroscale Preparation 316 EXPERIMENT 21 Quantitative Analysis of Grignard Reagents: 1-Methylbutylmagnesium Bromide and Phenylmagnesium Bromide 317 Reaction 318 Discussion 318 Experimental Procedure 319 EXPERIMENT 22 Williamson Synthesis of Ethers 321 Reaction 321 Discussion 322 Experiment 22A Propyl p-Tolyl Ether 323 Experimental Procedure 323 Optional Macroscale Preparation 324 Experiment 22B Methyl p-Ethylphenyl Ether 327 Reaction 327 Experimental Procedure 327 Optional Semimicroscale and Macroscale Preparations 329 Experiment 22C Butyl p-Nitrophenyl Ether: Preparation Using a Monomode Microwave Apparatus 332 Reaction 332 Experimental Procedure 332 Experiment 22D Butyl p-Nitrophenyl Ether: Preparation Using a Multimode Microwave Apparatus 334 Reaction 334 Experimental Procedure 334 EXPERIMENT 23 Amide Synthesis: Acetanilide and N,N?-Diacetyl-1,4-phenylenediamine 338 Reaction 338 Discussion 339 Experiment 23A Acetanilide 341 Experimental Procedure 341 Optional Semimicroscale Preparation 342 Experiment 23B N,N?-Diacetyl-1,4-phenylenediamine 343 Reaction 343 Experimental Procedure 343 EXPERIMENT 24 Imide Synthesis: N-Phenylmaleimide 346 Reaction 346 Discussion 347 Experiment 24A Maleanilic Acid 348 Experimental Procedure 348 Reaction 348 Experiment 24B N-Phenylmaleimide 349 Reaction 349 Experimental Procedure 350 EXPERIMENT 25 Synthesis of Cyclic Carboxylic Acid Anhydrides: Succinic Anhydride and Phthalic Anhydride 352 Reaction 352 Discussion 352 Experiment 25A Succinic Anhydride 354 Experimental Procedure 354 Experiment 25B Phthalic Anhydride 355 Reaction 355 Experimental Procedure 355 EXPERIMENT 26 Diazonium Coupling Reaction: Methyl Red 356 Reaction 357 Discussion 357 Experimental Procedure 359 EXPERIMENT 27 Friedel?Crafts Acylation: Acetylferrocene and Diacetylferrocene 361 Reaction 362 Discussion 362 Experimental Procedure 364 EXPERIMENT 28 Halogenation: Electrophilic Aromatic Substitution to Yield 4-Bromoacetanilide 368 Reaction 368 Discussion 369 Experimental Procedure 369 EXPERIMENT 29 Nitration: 2,5-Dichloronitrobenzene; N,N?-Diacetyl-2,3-dinitro-1,4-phenylenediamine; 5-Nitrosalicylic Acid; and 2- and 4-Nitrophenol 373 General Reaction 374 Discussion 374 Semimicroscale Preparation of Anhydrous Nitric Acid 375 Experimental Procedure 376 Experiment 29A 2,5-Dichloronitrobenzene 376 Reaction 376 Experimental Procedure 377 Experiment 29B N,N-Diacetyl-2,3-dinitro-1,4-phenylenediamine 378 Reaction 378 Experimental Procedure 378 Experiment 29C 5-Nitrosalicylic Acid 379 Reaction 379 Experimental Procedure 380 Experiment 29D 2- and 4-Nitrophenol 381 Reaction 381 Experimental Procedure 381 EXPERIMENT 30 Nucleophilic Aromatic Substitution: 2,4-Dinitrophenylthiocyanate 384 Reaction 385 Discussion 385 Experimental Procedure 386 Experiment 30-1 2,4-Dinitrophenylthiocyanate: Preparation Using a Monomode Microwave Apparatus 387 Experimental Procedure 387 Experiment 30-2 2,4-Dinitrophenylthiocyanate: Preparation Using a Multimode Microwave Apparatus 388 Experimental Procedure 388 EXPERIMENT 31 Halogenation Using N-Bromosuccinimide: 9-Bromoanthracene 390 Reaction 390 Discussion 391 Initiation Step 391 Propagation Step 391 Experimental Procedure 392 EXPERIMENT 32 Hypochlorite Oxidation of an Alcohol: Cyclohexanone 394 Reaction 394 Discussion 394 Experimental Procedure 395 EXPERIMENT 33 Chromium Trioxide?Resin or Hypochlorite Oxidation of an Alcohol: 9-Fluorenone 398 Experiment 33A 9-Fluorenone: CrO3 Oxidation of 9-Fluorenol 398 Reaction 398 Discussion 398 Experimental Procedure 399 Experiment 33B 9-Fluorenone: NaOCl Oxidation of 9-Fluorenol 401 Reaction 401 Discussion 401 Experimental Procedure 401 EXPERIMENT 34 Hypochlorite Oxidation of Methyl Ketones by the Haloform Reaction: Benzoic Acid and p-Methoxybenzoic Acid 403 Reaction 404 Discussion 404 Experiment 34A Benzoic Acid 405 Experimental Procedure 405 Experiment 34B p-Methoxybenzoic Acid 406 Reaction 406 Experimental Procedure 406 Optional Semimicroscale Preparation 407 EXPERIMENT 35 Conversion of Cyclohexyl Bromide to Cyclohexene?An E2 Elimination Reaction: Factors Affecting the Rate of a Chemical Reaction 409 Reaction 409 Discussion 409 Experimental Procedure 414 Data Analysis 416 Variation of Parameters 416 EXPERIMENT 36 Aqueous Suzuki Synthesis of 4-Phenylphenol 421 Reaction 421 Discussion 421 Experimental Procedure 424 Chapter 7 SEQUENTIAL SYNTHESES: THE TRANSITION FROM MACRO TO MICRO 428 SEQUENCE A The Synthesis of Hexaphenylbenzene 431 EXPERIMENTS A1a, A2a, A3a, A1b, A2b, A3b, and A4ab The Synthesis of Hexaphenylbenzene from Benzaldehyde: 434 Experiment A1a The Benzoin Condensation of Benzaldehyde: Benzoin 436 Reaction 436 Discussion 437 Semimicroscale Experimental Procedure 438 Optional Scales 439 Microscale Reaction Procedure 439 Experiment A2a Copper(II) Ion Oxidation of Benzoin: Benzil 440 Reaction 441 Discussion 441 Semimicroscale Experimental Procedure 442 Optional Microscale Preparation 444 Experiment A3a Tetraphenylcyclopentadienone 445 Reaction 445 Discussion 446 Microscale Reaction Procedure (1) 446 Microscale Reaction Procedure (2) 447 Experiment A1b (E)-Stilbene 448 Reaction 449 Discussion 449 Experimental Procedure 450 Experiment A2b Bromination of (E)-Stilbene: meso-Stilbene Dibromide 451 Reaction 452 Discussion 452 Semimicroscale Experimental Procedure 454 Experiment A3b Dehydrohalogenation of meso-Stilbene Dibromide: Diphenylacetylene 457 Reaction 457 Discussion 457 Semimicroscale Experimental Procedure 458 Optional Macroscale and Microscale Preparations 459 Experiment A4ab Hexaphenylbenzene 460 Reaction 461 Discussion 461 Experimental Procedure 462 SEQUENCE B The Stepwise Synthesis of Nylon-6,6 464 Experiment B1 Oxidation of Cyclohexanol: Adipic Acid 465 Reaction 465 Discussion 465 Experimental Procedure 467 Experiment B2 Preparation of an Acid Chloride: Adipoyl Chloride 468 Reaction 468 Discussion 469 Experimental Procedure 469 Experiment B3 Preparation of a Polyamide: Nylon-6,6 471 Reaction 471 Discussion 471 Experimental Procedure 472 SEQUENCE C The Synthesis of Sulfanilamide 473 The Sulfa Drugs 473 Experiment C1 Acetylation of Aniline: 2,2,2-Trifluoroacetanilide 474 Reaction 475 Discussion 475 Experimental Procedure 476 Experiment C2 Chlorosulfonation of 2,2,2- Trifluoroacetanilide: p-(Trifluoroacetamido) benzenesulfonyl Chloride 477 Reaction 478 Discussion 478 Experimental Procedure 479 Experiment C3 Preparation of an Arene Sulfonamide: Sulfanilamide 480 Discussion 481 Experimental Procedure 481 Chapter 8 SPECTROSCOPIC IDENTIFICATION OF ORGANIC COMPOUNDS 484 Infrared Spectroscopy 484 Introduction to Group Frequencies: Interpretation of Infrared Spectra 485 A Survey of Group Frequencies Identified in Organic Molecules 488 Group Frequencies of the Hydrocarbons 489 Group Frequencies of Carbonyl Groups: C O 490 Group Frequencies of the Heteroatom Functional Groups 492 Esters 493 Infrared Spectroscopy Instrumentation and Sample Handling 496 Instrumentation 496 Sample Handling in the Infrared 497 Nuclear Magnetic Resonance Spectroscopy 504 Nuclear spin 504 Instrumentation 505 Chemical Shift 508 Spin?Spin Coupling 509 Intensities 512 Second-Order Effects 513 Interpretation of 1H NMR Spectra 514 1H Chemical Shifts 517 Spin?Spin Coupling 518 Geminal Coupling 518 Vicinal Coupling 518 Long-Range Coupling 520 Examples of Complex, Yet First-Order, Coupling 520 Ethyl Vinyl Ether 520 Allyl Acetate 522 13C NMR Spectroscopy 525 Two-Dimensional NMR Spectroscopy 531 Nuclear Magnetic Resonance Sampling 532 Ultraviolet?Visible Spectroscopy: Introduction to Absorption Spectroscopy 537 UV?VIS Spectroscopy 539 Application to Organic Molecules 540 Instrumentation 547 The Source of Radiation 548 The Monochromator 549 Sample Compartment 550 The Detector 550 The Electronics: The Amplifier and Recorder 550 Sample Preparation 551 Criteria for Choosing a Solvent 552 Mass Spectrometry 553 Instrumentation 555 Ion Source 556 Mass Analyzer 557 Detector 559 Tuning the Mass Spectrometer 559 Sample Introduction 560 Gas Chromatography/Mass Spectrometry (GC/MS) 560 Capillary Columns 560 Split Injection 561 Split/Splitless Injection 561 Features of the Mass Spectrum 562 Terms 563 Isotope Peaks 563 Recognizing the Molecular Ion 565 Mass Spectral Interpretation 566 Case Study: Synthesis of Methyl Benzoate 567 Chapter 9 QUALITATIVE IDENTIFICATION OF ORGANIC COMPOUNDS 573 Organic Qualitative Analysis 573 Preliminary Tests 575 Nonchemical Tests 575 Ignition Test 576 Separation of Impurities 577 Detection of Elements Other Than Carbon, Hydrogen, or Oxygen 578 Sodium Fusion 578 Sulfur 579 Nitrogen 580 The Halogens (Except Fluorine) 580 Solubility Characteristics 582 The Classification Tests 584 Alcohols 584 Periodic Acid: Vicinal Diols 586 Aldehydes and Ketones 586 Alkanes and Cycloalkanes: Saturated Hydrocarbons 588 Alkenes and Alkynes: Unsaturated Hydrocarbons 589 Alkyl Halides 589 Amides, Ammonium Salts, and Nitriles 591 Amines 592 Aromatic Hydrocarbons with no Functional Groups 593 Carboxylic Acids 594 Esters 594 Ethers 595 Methyl Ketones and Methyl Carbinols 595 Nitro Compounds 596 Phenols and Enols 597 Preparation of Derivatives 598 Carboxylic Acids 599 Preparation of Acid Chlorides 599 Amides 599 Anilides 600 Toluidides 600 Alcohols 600 Phenyl- and -Naphthylurethanes (Phenyl- and -Naphthylcarbamates) 600 3,5-Dinitrobenzoates 601 Aldehydes and Ketones 602 2,4-Dinitrophenylhydrazones 602 Semicarbazones 602 Amines 602 Primary and Secondary Amines: Acetamides 602 Primary and Secondary Amines: Benzamides 603 Primary, Secondary, and Tertiary Amines: Picrates 603 Acid Chlorides and Anhydrides 604 Amides 604 Aromatic Hydrocarbons 604 Picrates 604 Nitriles 604 Hydrolysis to Amides 604 Phenols 605 -Naphthylurethanes (-Naphthylcarbamates) 605 Bromo Derivatives 605 Aliphatic Hydrocarbons, Halogenated Hydrocarbons, Amides, Nitro Compounds, Ethers, and Esters 606 Glossary 609 Index 612

About the Author

Dana W. Mayo holds the Charles Weston Pickard Research Professor of Chemistry Chair at Bowdoin College.During the summers of 1960-1971 he co-directed with Professor R.C. Lord one-week Summer Courses on the Technique and Applications of Infrared Spectroscopy at MIT. From 1972-81 he continued to co-direct these programs at Bowdoin College and became Director in 1982. Ronald M. Pike is the author of Microscale Organic Laboratory with Multistep and Multiscale Syntheses, Binder Ready Version, 6th Edition, published by Wiley. David C. Forbes is the author of Microscale Organic Laboratory with Multistep and Multiscale Syntheses, Binder Ready Version, 6th Edition, published by Wiley.

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