Chemistry CourseMate with eBook for Pavia/Lampman/Kriz/Engel's A Small Scale Approach to Organic Laboratory Techniques, 3rd Edition, [Instant Access], 2 terms (12 months)

Pavia Donald L. A small-scale approach to organic laboratory techniques 3 ed. [Brooks-Cole laboratory series for organic chemistry] 2011 [pdf 1028sc 1005+5c. 17.19mb] Featuring new experiments, a new essay, and new coverage of nanotechnology, this organic chemistry laboratory textbook offers a comprehensive treatment of laboratory techniques including small scale and some microscale methods that use standard-scale ("macroscale") glassware and equipment. The book is organized based on essays and topics of current interest and covers a large number of traditional organic reactions and syntheses, as well as experiments with a biological or health science focus. Seven introductory technique-based experiments, thirteen project-based experiments, and sections on green chemistry and biofuels spark students' interest and engage them in the learning process. Instructors may choose to offer Cengage Learning's optional Premium Website, which contains videos on basic organic laboratory techniques. Cover Page......Page 1 Title Page......Page 2 Copyright......Page 3 Preface......Page 6 NEW TO THIS EDITION......Page 7 SUPPORTING RESOURCES......Page 8 ACKNOWLEDGMENTS......Page 9 STRUCTURE OF THE EXPERIMENTS......Page 12 Contents......Page 14 ORGANIZATION OF THE TEXTBOOK......Page 21 BUDGETING TIME......Page 22 PURPOSE......Page 23 PART 1 Introduction to Basic Laboratory Techniques......Page 24 NOTES TO THE INSTRUCTORS......Page 25 PROCEDURE......Page 26 PROCEDURE......Page 30 REPORT......Page 31 QUESTIONS......Page 32 2 Crystallization......Page 35 SUGGESTED WASTE DISPOSAL......Page 36 PROCEDURE......Page 37 PROCEDURE......Page 39 PROCEDURE......Page 40 REPORT......Page 42 3 Extraction......Page 43 SUGGESTED WASTE DISPOSAL......Page 44 PROCEDURE......Page 45 PROCEDURE......Page 46 PROCEDURE......Page 47 PROCEDURE......Page 49 REPORT......Page 50 QUESTION......Page 51 4 A Separation and Purification Scheme......Page 52 4A Extractions with a Separatory Funnel......Page 53 4B Extractions with a Screw-Cap Centrifuge Tube......Page 54 5 Chromatography......Page 55 5A Thin-Layer Chromatography......Page 56 5B Selecting the Correct Solvent for Thin-Layer Chromatography......Page 58 5C Monitoring a Reaction with Thin-Layer Chromatography......Page 59 5D Column Chromatography......Page 60 6 Simple and Fractional Distillation......Page 63 SUGGESTED WASTE DISPOSAL......Page 64 PROCEDURE......Page 65 ANALYSIS......Page 67 7 Infrared Spectroscopy and Boiling-Point Determination......Page 68 NOTES TO THE INSTRUCTOR......Page 69 PROCEDURE......Page 70 Essay Aspirin......Page 72 8 Acetylsalicylic Acid......Page 75 REQUIRED READING......Page 76 PROCEDURE......Page 77 QUESTIONS......Page 78 Essay Analgesics......Page 79 9 Acetaminophen......Page 83 PROCEDURE......Page 84 Essay Identification of Drugs......Page 86 REFERENCES......Page 87 10 TLC Analysis of Analgesic Drugs......Page 88 NOTES TO THE INSTRUCTOR......Page 89 PROCEDURE......Page 90 Essay Caffeine......Page 92 REFERENCES......Page 95 11 Isolation of Caffeine from Tea Leaves......Page 96 11A Isolation of Caffeine from Tea Leaves......Page 99 11B Isolation of Caffeine from a Tea Bag......Page 101 Essay Esters—Flavors and Fragrances......Page 103 REFERENCES......Page 106 REQUIRED READING......Page 107 PROCEDURE......Page 108 QUESTIONS......Page 109 Essay Terpenes and Phenylpropanoids......Page 110 SPECIAL INSTRUCTIONS......Page 114 PROCEDURE......Page 115 QUESTIONS......Page 116 Essay Stereochemical Theory of Odor......Page 117 REFERENCES......Page 121 14 Spearmint and Caraway Oil: (+)- and (–)-Carvones......Page 122 REQUIRED READING......Page 123 NOTES TO THE INSTRUCTOR......Page 124 PROCEDURE......Page 125 QUESTIONS......Page 129 Essay The Chemistry of Vision......Page 130 REFERENCES......Page 134 15 Isolation of Chlorophyll and Carotenoid Pigments from Spinach......Page 135 NOTES TO THE INSTRUCTOR......Page 136 PROCEDURE......Page 137 QUESTIONS......Page 141 Essay Ethanol and Fermentation Chemistry......Page 142 REFERENCES......Page 144 16 Ethanol from Sucrose......Page 145 NOTES TO THE INSTRUCTOR......Page 146 PROCEDURE......Page 147 QUESTIONS......Page 149 PART 2 Introduction to Molecular Modeling......Page 150 MOLECULAR MECHANICS......Page 151 MINIMIZATION AND CONFORMATION......Page 152 LIMITATIONS OF MOLECULAR MECHANICS......Page 154 17 An Introduction to Molecular Modeling......Page 155 17A The Conformations of n-Butane: Local Minima......Page 156 17B Cyclohexane Chair and Boat Conformations......Page 157 17C Substituted Cyclohexane Rings (Critical Thinking Exercises)......Page 158 17D cis- and trans-2-Butene......Page 159 INTRODUCTION TO TERMS AND METHODS......Page 160 BASIS-SET ORBITALS......Page 161 SEMIEMPIRICAL METHODS......Page 163 HEATS OF FORMATION......Page 164 GRAPHIC MODELS AND VISUALIZATION......Page 165 SURFACES......Page 166 REFERENCES......Page 167 18 Computational Chemistry......Page 168 18A Heats of Formation: Isomerism,Tautomerism, and Regioselectivity......Page 169 18B Heats of Reaction: SN1 Reaction Rates......Page 171 18D Density–Electrostatic Potential Maps: Carbocations......Page 172 18E Density–LUMO Maps: Reactivities of Carbonyl Groups......Page 173 PART 3 Properties and Reactions of Organic Compounds......Page 176 19 Reactivities of Some Alkyl Halides......Page 177 NOTES TO THE INSTRUCTOR......Page 178 PROCEDURE......Page 179 MOLEULAR MODELING (OPTIONAL)......Page 180 QUESTIONS......Page 181 20 Nucleophilic Substitution Reactions: Competing Nucleophiles......Page 182 20A Competitive Nucleophiles with 1-Butanol or 2-Butanol......Page 184 20B Competitive Nucleophiles with 2-Methyl-2-Propanol......Page 187 20C Analysis......Page 188 21 Synthesis of n-Butyl Bromide and t-Pentyl Chloride......Page 191 21A n-Butyl Bromide......Page 194 21B t-Pentyl Chloride......Page 196 22 4-Methylcyclohexene......Page 198 SUGGESTED WASTE DISPOSAL......Page 199 PROCEDURE......Page 200 QUESTIONS......Page 201 Essay Fats and Oils......Page 202 REFERENCES......Page 207 REQUIRED READING......Page 208 NOTES TO THE INSTRUCTOR......Page 209 PROCEDURE......Page 210 QUESTIONS......Page 212 Essay Petroleum and Fossil Fuels......Page 213 REFERENCES......Page 221 REQUIRED READING......Page 222 NOTES TO THE INSTRUCTOR......Page 223 PROCEDURE......Page 224 Essay Biofuels......Page 226 REFERENCES......Page 229 25 Biodiesel......Page 230 25A Biodiesel from Coconut Oil......Page 232 25C Analysis of Biodiesel......Page 233 26 Ethanol from Corn......Page 235 SPECIAL INSTRUCTIONS......Page 236 PROCEDURE......Page 237 REFERENCES......Page 238 Essay Green Chemistry......Page 239 REFERENCES......Page 244 27 Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination......Page 245 27A Chiral Reduction of Ethyl Acetoacetate......Page 246 27B NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate......Page 249 28 Nitration of Aromatic Compounds Using a Recyclable Catalyst......Page 255 SUGGESTED WASTE DISPOSAL......Page 256 PROCEDURE......Page 257 QUESTIONS......Page 258 29 Reduction of Ketones Using Carrots as Biological Reducing Agents......Page 259 SPECIAL INSTRUCTIONS......Page 260 30 Resolution of (±)- 1⁄2 Phenylethylamine and Determination of Optical Purity......Page 261 30A Resolution of (±)- 1⁄2 Phenylethylamine......Page 264 30B Determination of Optical Purity Using NMR and a Chiral Resolving Agent......Page 267 31 An Oxidation–Reduction Scheme: Borneol, Camphor, Isoborneol......Page 270 SPECIAL INSTRUCTIONS......Page 273 PROCEDURE......Page 274 QUESTIONS......Page 283 32 Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid......Page 284 32A Preparation of Benzoin by Thiamine Catalysis......Page 285 32B Preparation of Benzil......Page 291 32C Preparation of Benzilic Acid......Page 293 33 Triphenylmethanol and Benzoic Acid......Page 297 33A Triphenylmethanol......Page 303 33B Benzoic Acid......Page 305 34 Aqueous-Based Organozinc Reactions......Page 308 SUGGESTED WASTE DISPOSAL......Page 309 PROCEDURE......Page 310 35 Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes using a Palladium Catalyst......Page 311 BACKGROUND......Page 312 PROCEDURE......Page 314 OPTIONAL PROCEDURE USING MICROWAVE TECHNOLOGY......Page 319 QUESTIONS......Page 320 36 Grubbs-Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product......Page 321 SPECIA L INSTRUCTIONS......Page 323 PROCEDURE......Page 324 REFERENCES......Page 327 37 The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones)......Page 328 PROCEDURE......Page 329 Molecular Modeling (Optional)......Page 330 QUESTIONS......Page 331 38 A Green Enantioselective Aldol Condensation Reaction......Page 332 SPECIAL INSTRUCTIONS......Page 334 PROCEDURE......Page 335 39 Preparation of an α, β -Unsaturated Ketone via Michael and Aldol Condensation Reactions......Page 339 PROCEDURE......Page 340 QUESTIONS......Page 342 40 Preparation of Triphenylpyridine......Page 343 SAFETY PRECAUTIONS......Page 344 REFERENCES......Page 345 41 1,4-Diphenyl-1,3-Butadiene......Page 346 REQUIRED READING......Page 348 PROCEDURE......Page 349 42 Relative Reactivities of Several Aromatic Compounds......Page 352 REQUIRED READING......Page 354 PROCEDURE......Page 355 43 Nitration of Methyl Benzoate......Page 357 SUGGESTED WASTE DISPOSAL......Page 359 Molecular Modeling (Optional)......Page 360 QUESTIONS......Page 361 Essay Local Anesthetics......Page 362 REFERENCES......Page 365 REQUIRED READING......Page 366 PROCEDURE......Page 367 Essay Pheromones: Insect Attractants and Repellents......Page 369 SEX ATTRACTANTS......Page 370 OTHER PHEROMONES......Page 372 INSECT REPELLENTS......Page 373 REFERENCES......Page 375 45 N,N-Diethyl-m-toluamide: The Insect Repellent “OFF”......Page 377 SPECIAL INSTRUCTIONS......Page 378 PROCEDURE......Page 379 QUESTIONS......Page 381 Essay Sulfa Drugs......Page 382 REFERENCES......Page 384 46 Sulfa Drugs: Preparation of Sulfanilamide......Page 385 SPECIAL INSTRUCTIONS......Page 386 PROCEDURE......Page 387 QUESTIONS......Page 389 CHEMICAL STRUCTURES OF POLYMERS......Page 390 THERMAL CLASSIFICATION OF POLYMERS......Page 391 ADDITION POLYMERS......Page 392 CONDENSATION POLYMERS......Page 393 REFERENCES......Page 399 47 Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene......Page 401 47A Polyesters......Page 402 47B Polyamide (Nylon)......Page 404 47C Polystyrene......Page 405 47D Infrared Spectra of Polymer Samples......Page 407 48 Ring-Opening Metathesis Polymerization (ROMP) using a Grubbs Catalyst: a Three-Step Synthesis of a Polymer......Page 409 48A Diels-Alder Reaction......Page 412 48B Conversion of the Diels-Alder Adduct to the Diester......Page 413 48C Synthesizing a Polymer by Ring-Opening Metathesis Polymerization (ROMP)......Page 415 Essay Diels–Alder Reaction and Insecticides......Page 419 ALTERNATIVES TO INSECTICIDES......Page 422 49 The Diels–Alder Reaction of Cyclopentadiene with Maleic Anhydride......Page 424 NOTES TO THE INSTRUCTOR......Page 425 PROCEDURE......Page 426 Molecular Modeling (Optional)......Page 427 QUESTIONS......Page 428 SAFETY PRECAUTIONS......Page 429 51 Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone......Page 430 51A Photoreduction of Benzophenone......Page 431 51B Synthesis of β -Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol......Page 438 Essay Fireflies and Photochemistry......Page 440 REFERENCES......Page 442 52 Luminol......Page 443 SPECIAL INSTRUCTIONS......Page 445 PROCEDURE......Page 446 Essay The Chemistry of Sweeteners......Page 447 53 Carbohydrates......Page 450 NOTES TO THE INSTRUCTOR......Page 451 54 Analysis of a Diet Soft Drink by HPLC......Page 460 SUGGESTED WASTE DISPOSAL......Page 461 PROCEDURE......Page 462 REFERENCES......Page 463 PART 4 Identification of Organic Substances......Page 464 55 Identification of Unknowns......Page 465 55A Solubility Tests......Page 472 55B Tests for the Elements (N, S, X)......Page 477 55C Tests for Unsaturation......Page 483 55D Aldehydes and Ketones......Page 487 55E Carboxylic Acids......Page 494 55F Phenols......Page 496 55G Amines......Page 499 55H Alcohols......Page 502 55I Esters......Page 507 PART 5 Project-Based Experiments......Page 512 SPECIAL INSTRUCTIONS......Page 513 PROCEDURE......Page 514 57 Isolation of Essential Oils from Allspice, Caraway, Cinnamon, Cloves, Cumin, Fennel, or Star Anise......Page 516 57A Isolation of Essential Oils by Steam Distillation......Page 519 57B Identification of the Constituents of Essential Oils by Gas Chromatography–Mass Spectrometry......Page 521 57C Investigation of the Essential Oils of Herbs and Spices—A Mini-Research Project......Page 522 SPECIAL INSTRUCTIONS......Page 523 PROCEDURE......Page 524 GAS CHROMATOGRAPHY......Page 526 59 Friedel–Crafts Acylation......Page 527 REQUIRED READING......Page 529 NOTES TO THE INSTRUCTOR......Page 530 PROCEDURE......Page 531 REFERENCES......Page 533 QUESTIONS......Page 534 SPECIAL INSTRUCTIONS......Page 535 PROCEDURE......Page 536 61 Carbonation of an Unknown Aromatic Halide......Page 537 PROCEDURE......Page 538 62 The Aldehyde Enigma......Page 539 PROCEDURE......Page 540 REPORT......Page 541 63 Synthesis of Substituted Chalcones: A Guided-Inquiry Experience......Page 542 NOTES TO THE INSTRUCTOR......Page 543 PROCEDURE......Page 544 QUESTIONS......Page 546 64 Green Epoxidation of Chalcones......Page 547 PROCEDURE......Page 548 QUESTIONS......Page 550 65 Cyclopropanation of Chalcones......Page 551 PROCEDURE......Page 552 QUESTIONS......Page 553 66 Michael and Aldol Condensation Reactions......Page 554 PROCEDURE......Page 556 67 Esterification Reactions of Vanillin: The Use of NMR to Determine a Structure......Page 558 PROCEDURE......Page 559 68 An Oxidation Puzzle......Page 560 SUGGESTED WASTE DISPOSAL......Page 561 REPORT......Page 562 PART 6 The Techniques......Page 564 1.1 Safety Guidelines......Page 565 1.2 Right-to-Know Laws......Page 570 1.3 Common Solvents......Page 578 1.4 Carcinogenic Substances......Page 580 REFERENCES......Page 581 2 The Laboratory Notebook, Calculations, and Laboratory Records......Page 582 2.2 Notebook Format......Page 583 2.4 Submission of Samples......Page 589 3.1 Cleaning Glassware......Page 590 3.2 Drying Glassware......Page 591 3.4 Connecting Ground- Glass Joints......Page 592 3.5 Capping Flasks, Conical Vials, and Openings......Page 593 3.9 Description of Equipment......Page 594 4.1 CRC Handbook of Chemistry and Physics......Page 598 4.2 Lange’s Handbook of Chemistry......Page 600 4.3 The Merck index......Page 602 4.4 Aldrich Handbook of Fine Chemicals......Page 603 PROBLEMS......Page 604 5 Measurement of Volume and Weight......Page 605 5.1 Graduated Cylinders......Page 606 5.2 Dispensing Pumps......Page 607 5.3 Graduated Pipets......Page 608 5.4 Pasteur Pipets......Page 612 5.5 Syringes......Page 613 5.6 Automatic Pipets......Page 614 5.8 Balances......Page 615 PROBLEMS......Page 616 6.1 Heating Mantles......Page 617 6.4 Oil Bath with Hot Plate/Stirrer......Page 619 6.5 Aluminum Block with a Hot Plate/Stirrer......Page 621 6.6 Sand Bath with Hot Plate/Stirrer......Page 623 6.7 Flames......Page 624 6.8 Steam Baths......Page 625 6.9 Cold Baths......Page 626 7 Reaction Methods......Page 627 7.1 Assembling the Apparatus......Page 628 7.2 Heating Under Reflux......Page 631 7.3 Stirring Methods......Page 633 7.5 Addition of Liquid Reagents......Page 634 7.7 Reactions Conducted under an Inert Atmosphere......Page 636 7.8 Capturing Noxious Gases......Page 638 7.9 Collecting Gaseous Products......Page 641 7.10 Evaporation of Solvents......Page 643 7.12 Microwave-Assisted Organic Chemistry......Page 645 PROBLEMS......Page 647 8.1 Gravity Filtration......Page 649 8.2 Filter Paper......Page 654 8.3 Vacuum Filtration......Page 655 8.4 Filtering Media......Page 656 8.5 The Aspirator......Page 657 8.7 Craig Tubes......Page 659 PROBLEM......Page 661 9.2 The Melting Point......Page 662 9.3 Melting-Point Theory......Page 663 9.6 Determining the Melting Point—The Thiele Tube......Page 665 9.7 Determining the Melting Point—Electrical Instruments......Page 666 9.8 Decomposition, Discoloration, Softening, Shrinkage, and Sublimation......Page 668 9.9 Thermometer Calibration......Page 670 PROBLEMS......Page 671 10.1 Definition of Solubility......Page 672 10.2 Predicting Solubility Behavior......Page 673 10.3 Organic Solvents......Page 678 PROBLEMS......Page 679 11.1 Solubility......Page 681 11.2 Theory Of Crystallization......Page 683 11.3 Macroscale Crystallization......Page 684 11.5 Selecting a Solvent......Page 691 11.6 Testing Solvents for Crystallization......Page 693 11.7 Decolorization......Page 694 11.8 Inducing Crystallization......Page 695 11.9 Drying Crystals......Page 696 PROBLEMS......Page 698 12.1 Extraction......Page 700 12.2 Distribution Coefficient......Page 701 12.3 Choosing an Extraction Method and a Solvent......Page 703 12.4 The Separatory Funnel......Page 705 12.5 The Conical Vial—Separating the Lower Layer......Page 707 12.6 The Conical Vial—Separating the Upper Layer......Page 709 12.8 How Do You Determine Which One Is the Organic Layer?......Page 712 12.9 Drying Agents......Page 713 12.10 Emulsions......Page 718 12.11 Purification and Separation Methods......Page 719 12.12 Continuous Solid–Liquid Extraction......Page 721 12.13 Continuous Liquid– Liquid Extraction......Page 722 12.14 Solid Phase Extraction......Page 723 PROBLEMS......Page 726 13.1 The Boiling Point......Page 728 13.2 Determining the Boiling Point—Macroscale Methods......Page 729 13.3 Determining the Boiling Point—Microscale Methods......Page 731 13.4 Thermometers and Stem Corrections......Page 734 13.6 Density......Page 736 PROBLEMS......Page 737 14.1 The Evolution of Distillation Equipment......Page 738 14.2 Distillation Theory......Page 740 14.3 Simple Distillation—Standard Apparatus......Page 742 14.4 Microscale and Semi- Microscale Equipment......Page 745 15 Fractional Distillation, Azeotropes......Page 748 15.1 Differences between Simple and Fractional Distillation......Page 749 15.2 Vapor–Liquid Composition Diagrams......Page 751 15.3 Raoult’s Law......Page 752 15.5 Types of Fractionating Columns and Packings......Page 755 15.6 Fractional Distillation: Methods and Practice......Page 757 15.7 Nonideal Solutions: Azeotropes......Page 759 15.8 Azeotropic Distillation: Applications......Page 763 PROBLEMS......Page 766 16.1 Macroscale Methods......Page 768 16.2 Vacuum Distillation: Stepwise Directions......Page 773 16.3 Rotary Fraction Collectors......Page 775 16.5 Bulb-to-Bulb Distillation......Page 776 16.6 The Mechanical Vacuum Pump......Page 777 16.7 The Closed-End Manometer......Page 779 16.8 Connecting and Using a Manometer......Page 781 17 Sublimation......Page 782 17.1 Vapor Pressure Behavior of Solids and Liquids......Page 783 17.2 Sublimation Behavior of Solids......Page 784 17.4 Advantages of Sublimation......Page 785 17.5 Sublimation—Methods......Page 786 17.6 Sublimation—Specific Directions......Page 787 18.1 Differences Between Distillation of Miscible and Immiscible Mixtures......Page 789 18.2 Immiscible Mixtures: Calculations......Page 791 18.3 Steam Distillation—Macroscale Methods......Page 792 18.4 Steam Distillation—Microscale Methods......Page 794 18.5 Steam Distillation—Semi-Microscale Methods......Page 795 19 Column Chromatography......Page 796 19.2 Interactions......Page 797 19.3 Principle of Column Chromatographic Separation......Page 798 19.4 Parameters Affecting Separation......Page 800 19.5 Packing the Column: Typical Problems......Page 805 19.6 Packing the Column: Preparing the Support Base......Page 806 19.7 Packing the Column: Depositing the Adsorbent—Dry Pack Methods......Page 809 19.8 Packing the Column: Depositing the Adsorbent—the Slurry Method......Page 810 19.9 Applying the Sample to the Column......Page 811 19.10 Elution Techniques......Page 812 19.11 Reservoirs......Page 813 19.12 Monitoring the Column......Page 814 19.15 Decolorization by Column Chromatography......Page 815 19.16 Gel Chromatography......Page 816 19.17 Flash Chromatography......Page 817 PROBLEMS......Page 819 20.1 Principles of Thin- Layer Chromatography......Page 820 20.3 Preparation of Thin- Layer Slides And Plates......Page 821 20.4 Sample Application: Spotting The Plates......Page 822 20.5 Developing (Running) TLC Plates......Page 824 20.7 Visualization Methods......Page 825 20.8 Preparative Plates......Page 826 20.9 The RfValue......Page 827 20.10 Thin-Layer Chromatography Applied in Organic Chemistry......Page 828 PROBLEMS......Page 830 21 High-Performance Liquid Chromatography (HPLC)......Page 831 21.1 Adsorbents and Columns......Page 833 21.2 Column Dimensions......Page 834 21.4 Detectors......Page 835 22 Gas Chromatography......Page 836 22.1 The Gas Chromatograph......Page 837 22.2 The Column......Page 838 22.3 Principles of Separation......Page 840 22.5 Advantages of Gas Chromatography......Page 841 22.6 Monitoring The Column (The Detector)......Page 842 22.7 Retention Time......Page 843 22.8 Chiral Stationary Phases......Page 844 22.10 Qualitative Analysis......Page 846 22.11 Collecting the Sample......Page 847 22.12 Quantitative Analysis......Page 849 22.13 Treatment of Data: Chromatograms Produced by Modern Data Stations......Page 851 22.14 Gas Chromatography-Mass Spectrometry (GC-MS)......Page 854 PROBLEMS......Page 855 23.1 Nature of Polarized Light......Page 856 23.2 The Polarimeter......Page 858 23.3 Sample Preparation, The Sample Cell......Page 859 23.4 Operation of the Polarimeter......Page 860 23.5 Optical Purity......Page 863 24.1 The Refractive Index......Page 864 24.2 The Abbé Refractometer......Page 865 24.4 The Digital Refractometer......Page 868 PROBLEMS......Page 869 25 Infrared Spectroscopy......Page 870 25.2 Liquid Samples—NaCl Plates......Page 871 25.3 Liquid Samples— AgCl Plates......Page 873 25.5 Solid Samples—KBr Pellets and Nujol Mulls......Page 875 25.6 Solid Samples—Solution Spectra......Page 879 25.7 Recording the Spectrum......Page 882 25.8 Calibration......Page 883 25.9 Uses of the Infrared Spectrum......Page 884 25.10 Modes of Vibration......Page 885 25.11 What to Look for in Examining Infrared Spectra......Page 886 25.13 Analyzing a Spectrum (Or What You Can Tell at a Glance)......Page 887 25.14 Survey of the Important Functional Groups......Page 890 REFERENCES......Page 903 PROBLEMS......Page 904 26 Nuclear Magnetic Resonance Spectroscopy (Proton NMR)......Page 905 PART A . PREPARING A SAMPLE FOR NMR SPECTROSCOPY......Page 907 26.1 Routine Sample Preparation Using Deuterated Chloroform......Page 908 26.2 Nonroutine Sample Preparation......Page 909 26.3 Reference Substances......Page 910 26.4 The Chemical Shift......Page 911 26.5 Chemical Equivalence—Integrals......Page 912 26.6 Chemical Environment and Chemical Shift......Page 914 26.7 Local Diamagnetic Shielding......Page 915 26.8 Anisotropy......Page 918 26.9 Spin–Spin Splitting ( n+1 Rule)......Page 919 26.10 The Coupling Constant......Page 921 26.11 Magnetic Equivalence......Page 923 26.12 Spectra at Higher Field Strength......Page 925 26.13 Aromatic Compounds—Substituted Benzene Rings......Page 926 26.14 Protons Attached to Atoms Other Than Carbon......Page 932 26.15 Chemical Shift Reagents......Page 933 REFERENCES......Page 935 PROBLEMS......Page 936 27.1 Preparing a Sample for Carbon-13 NMR......Page 942 27.2 Carbon-13 Chemical Shifts......Page 943 27.3 Proton-Coupled 13[sup (13)] C Spectra—Spin–Spin Splitting of Carbon-13 Signals......Page 944 27.4 Proton-Decoupled 13[sup (13)]C Spectra......Page 946 27.5 Some Sample Spectra—Equivalent Carbons......Page 948 27.6 Nuclear Overhauser Enhancement (NOE)......Page 949 27.7 Compounds with Aromatic Rings......Page 951 REFERENCES......Page 953 PROBLEMS......Page 954 28.1 The Mass Spectrum......Page 960 28.2 Molecular Formula Determination......Page 962 28.3 Detecting Halogens......Page 963 28.4 Fragmentation Patterns......Page 965 28.5 Interpreted Mass Spectra......Page 967 28.6 Rearrangement Reactions......Page 977 29.1 Locating Physical Constants: Handbooks......Page 978 29.3 Searching the Chemical Literature......Page 979 29.5 Advanced Textbooks......Page 980 29.6 Specific Synthetic Methods......Page 981 29.7 Advanced Laboratory Techniques......Page 982 29.8 Reaction Mechanisms......Page 983 29.10 Beilsteinand Chemical Abstracts......Page 984 29.11 Computer Online Searching......Page 987 29.12 Scientific Journals......Page 988 29.14 How to Conduct a Literature Search......Page 989 PROBLEMS......Page 990 APPENDICES......Page 992 1 Tables of Unknowns and Derivatives......Page 993 2 Procedures for Preparing Derivatives......Page 1006 3 Index of Spectra......Page 1011 INDEX......Page 1014

Featuring new experiments, a new essay, and new coverage of nanotechnology, this organic chemistry laboratory textbook offers a comprehensive treatment of laboratory techniques including small scale and some microscale methods that use standard-scale ("macroscale") glassware and equipment. The book is organized based on essays and topics of current interest and covers a large number of traditional organic reactions and syntheses, as well as experiments with a biological or health science focus. Seven introductory technique-based experiments, thirteen project-based experiments, and sections on green chemistry and biofuels spark students' interest and engage them in the learning process. Instructors may choose to offer Cengage Learning's optional Premium Website, which contains videos on basic organic laboratory techniques.

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