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 (±)- ½ Phenylethylamine and Determination of Optical Purity......Page 261
30A Resolution of (±)- ½ 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