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Preface | ||
Introduction: Getting Acquainted with the Laboratory | 1 | |
Pt. 1 | Experiments | 13 |
1 | Extraction of Caffeine from Tea | 15 |
2 | Purification and Thin-Layer Chromatographic Analysis of Caffeine | 22 |
3 | Synthesis of Ethanol by Fermentation of Sucrose | 27 |
4 | Synthesis of Salicylic Acid | 32 |
5 | Synthesis of Aspirin | 41 |
Optional Experiment: Thin-Layer Chromatographic Analysis of Analgesics | 47 | |
6 | Radical Chlorination Reactions | 49 |
7 | Isolation of Essential Oils and the Theory of Odor | 54 |
8 | Nucleophilic Substitution Reactions | 67 |
9 | Addition Reactions of Alkenes | 82 |
10 | Dehydrohalogenation of 2-Bromoheptane: Variation of Promoting Base | 103 |
11 | Dehydration of Alcohols | 108 |
12 | Ether Syntheses | 123 |
13 | Grignard Syntheses | 134 |
14 | Phase Transfer Catalysis | 160 |
15 | Oxidation Reactions | 171 |
16 | Diels-Alder Reactions | 188 |
17 | Electrophilic Aromatic Substitution | 201 |
18 | Acylation and Alkylation of Aromatic Compounds | 217 |
19 | Reduction Reactions of 3-Nitroacetophenone | 236 |
20 | Photochemistry: Photoreduction of Benzophenone and Rearrangement to Benzpinacolone | 244 |
21 | Aldol Condensation: Reaction of Benzaldehyde and Acetone | 252 |
22 | Synthesis of 2,3,4,5-Tetraphenylcyclopentadienone | 259 |
23 | Horner-Emmons-Wittig Synthesis of Methyl 4-Methoxy-E-Cinnamate | 267 |
24 | Kinetic Versus Thermodynamic Control in Chemical Reactions | 275 |
25 | Synthesis of Esters | 289 |
26 | Amide Chemistry | 305 |
27 | Polyphosphoric Acid-Catalyzed Beckmann Rearrangement of Acetophenone Oxime | 327 |
28 | Synthesis of trans-1,2-Dibfnzocyclopropane by Ring Closure | 333 |
29 | Polymer Chemistry | 339 |
Pt. 2 | Projects | 353 |
1 | Hydrolysis of an Unknown Ester | 355 |
2 | Synthesis of 1-Bromobutane and a Grignard Synthesis of an Alcohol | 369 |
3 | Synthesis and Dehydration of 3,3-Dimethyl-2-Butanol | 383 |
4 | Interconversion of 4-tert-Butylcyclohexanol and 4-tert-Butylcyclohexanone | 392 |
5 | Aldol Condensation Using an Unknown Aldehyde and an Unknown Ketone: Derivative Formation and Identification of Unknowns | 408 |
6 | Benzoin Chemistry: Synthesis of an Anticonvulsant Drug Using Biochemical Catalysis | 419 |
7 | Synthesis of Benzocaine | 435 |
8 | Resolution of R,S-Benzoylamino Acids | 443 |
9 | Multistep Synthesis of Para Red from Acetanilide | 456 |
10 | Syntheses Starting with Alkyl Halides | 467 |
11 | Diels-Alder Cycloadditions of Various Dienophiles to 2,3-Dimethyl-1,3-Butadiene | 471 |
12 | Multistep Synthesis of N-Phenyltetraphenyl-Phthalimide | 476 |
13 | Sugars: The Glucose Pentaacetates | 486 |
Pt. 3 | Organic Qualitative Analysis | 497 |
1 | Identification of Unknowns | 499 |
2 | Physical Properties | 502 |
3 | Classification by Solubility and Elemental Analysis by Sodium Fusion | 504 |
4 | Infrared, Nuclear Magnetic Resonance, and Mass Spectrometric Analysis | 516 |
5 | Classification Tests for Functional Groups | 524 |
6 | Synthesis of Solid Derivatives | 551 |
7 | Separation of Mixtures | 564 |
8 | Summary of Identification Procedure for an Unknown Compound | 572 |
9 | Summary of Analysis of Mixture of Unknown Compounds | 573 |
Pt. 4 | Spectrometric Methods | 577 |
1 | Infrared Spectrometry | 579 |
2 | NMR Spectrometry | 610 |
3 | Mass Spectrometry | 664 |
4 | Ultraviolet and Visible Spectrometry | 675 |
Integrated Problems | 683 | |
Pt. 5 | Techniques of the Organic Laboratory | 687 |
1 | Safety | 689 |
2 | Laboratory Glassware | 706 |
3 | Heating Methods | 714 |
4 | Extraction and Drying Agents | 724 |
5 | Recrystallization | 749 |
6 | Melting Points and Melting Ranges | 765 |
7 | Boiling Points, Distillation, and Azeotropes | 776 |
8 | Sublimation | 805 |
9 | Refractrometry | 808 |
10 | Thin-Layer Chromatography | 813 |
11 | Gas-Liquid Chromatography | 826 |
12 | Liquid Chromatography | 841 |
13 | Polarimetry | 857 |
App. A | Derivative Tables for Organic Qualitative Analysis | A-1 |
App. B | The Literature of Organic Chemistry | B-1 |
Index | I-1 |
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