| Preface |
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ix | |
| 1 Introduction |
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1 | (18) |
| 2 Laboratory Safety and Waste Disposal |
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19 | (13) |
| Techniques |
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32 | (18) |
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4 Melting Points, Boiling Points, and Refractive Indices |
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50 | (15) |
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65 | (12) |
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77 | (11) |
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7 Vacuum Distillation and Sublimation |
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88 | (15) |
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8 Extraction of Acids and Bases and the Isolation of Caffeine from Coffee, Tea, and Cola Syrup |
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103 | (20) |
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9 Thin-Layer Chromatography: Analysis of Analgesics and Isolation of Lycopene from Tomato Paste |
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123 | (15) |
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10 Column Chromatography: Acetylferrocene, Cholesteryl Acetate, and Fluorenone |
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138 | (10) |
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11 Alkenes from Alcohols: Analysis of a Mixture by Gas Chromatography |
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148 | (7) |
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155 | (22) |
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13 Nuclear Magnetic Resonance Spectroscopy |
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177 | (19) |
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14 Ultraviolet Spectroscopy and Mass Spectrometry |
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196 | (15) |
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15 Molecular Mechanics and Computational Chemistry |
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211 | (9) |
| Elimination, Substitution, and Addition |
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16 The SN2 Reaction: 1-Bromobutane |
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220 | (6) |
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17 Nucleophilic Substitution Reactions of Alkyl Halides |
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226 | (7) |
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18 Alkanes and Alkenes: Radical Initiated Chlorination of 1-Chlorobutane; Reactions of Alkanes and Alkenes |
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233 | (12) |
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19 Alkenes from Alcohols: Cyclohexene from Cyclohexanol |
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245 | (6) |
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20 Bromination and Debromination: Purification of Cholesterol |
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251 | (5) |
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256 | (8) |
| Oxidation and Reduction |
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22 Oxidation: Cyclohexanol to Cyclohexanone; Cyclohexanone to Adipic Acid |
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264 | (11) |
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23 Pulegone from Citronellol: Oxidation with Pyridinium á Chlorochromate |
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275 | (8) |
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24 Oxidative Coupling of Alkynes: 2,7-Dimethyl-3,5-octadiyn-2,7-diol |
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283 | (4) |
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25 Catalytic Hydrogenation |
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287 | (10) |
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26 Sodium Borohydride Reduction of 2-Methylcyclohexanone: A Problem in Conformational Analysis |
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297 | (6) |
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27 Epoxidation of Cholesterol |
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303 | (6) |
| Aromatic Substitution and Elimination |
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28 Nitration of Methyl Benzoate |
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309 | (5) |
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29 Friedel-Crafts Alkylation of Benzene and Dimethoxybenzene; Host-Guest Chemistry |
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314 | (11) |
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30 Alkylation of Mesitylene |
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325 | (7) |
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31 Reactions of Triphenylmethyl Carbocation, Carbanion, and Radical |
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332 | (12) |
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32 The Friedel-Crafts Reaction: Anthraquinone and Anthracene |
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344 | (8) |
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33 Friedel-Crafts Acylation of Ferrocene: Acetylferrocene |
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352 | (3) |
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34 1,2,3,4-Tetraphenylnaphthalene via Benzyne |
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355 | (4) |
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35 Triptycene via Benzyne |
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359 | (5) |
| Reactions of Aldehydes and Ketones |
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364 | (19) |
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37 Dibenzalacetone by the Aldol Condensation |
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383 | (5) |
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38 Grignard Synthesis of Triphenylmethanol and Benzoic Acid |
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388 | (13) |
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39 The Wittig and Wittig-Horner Reactions |
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401 | (6) |
| Reactions of Carboxylic Acids, Esters, and Amines |
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40 Esterification and Hydrolysis |
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407 | (9) |
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41 Acetylsalicylic Acid (Aspirin) |
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416 | (6) |
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42 Malonic Ester Synthesis of a Barbiturate |
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422 | (7) |
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429 | (10) |
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44 Separation and Purification of the Components of an Analgesic Tablet: Aspirin Caffeine, and Acetaminophen |
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439 | (5) |
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45 The Sandmeyer Reaction: 1-Bromo-4-chlorobenzene, 2-lodobenzoic Acid, and 4-Chlorotoluene |
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444 | (7) |
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46 Sulfanilamide from Nitrobenzene |
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451 | (13) |
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464 | (17) |
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481 | (8) |
| The Diels-Alder and Related Reactions |
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489 | (13) |
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50 Ferrocene [Bis(cyclopentadienyl)iron] |
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502 | (6) |
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51 p-Terphenyl by the Diels-Alder Reaction |
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508 | (3) |
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52 Tetraphenylcyclopentadienone |
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511 | (3) |
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53 Hexaphenylbenzene and Dimethyl Tetraphenylphthalate |
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514 | (5) |
| Derivatives of 1,2-Diphenylethane: A Multistep Synthesis |
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519 | (39) |
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54 The Benzoin Condensation: Cyanide Ion and Thiamine Catalyzed |
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521 | (5) |
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55 Nitric Acid Oxidation. Preparation of Benzil from Benzoin. Synthesis of a Heterocycle: Diphenylquinoxaline |
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526 | (6) |
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56 Borohydride Reduction of a Ketone: Hydrobenzoen from Benzil |
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532 | (3) |
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57 Synthesis of 2,2-Dimethyl- 1,5-dioxolane. The Acetonide Derivative of a Vicinal Diol |
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535 | (3) |
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58 1,4-Addition: Reductive Acetylation of Benzil |
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538 | (4) |
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59 Synthesis of an Alkyne from an Alkene. Bromination and Dehydrobromination: Stilbene and Diphenylacetylene |
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542 | (7) |
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60 The Perkin Reaction: Synthesis of a-Phenylcinnamic Acid |
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549 | (5) |
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61 Decarboxylation: Synthesis of cis-Stilbene |
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554 | (4) |
| Photochemistry |
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62 Chemiluminescence: Syntheses of Cyalume and Luminol |
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558 | (8) |
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63 Photochemistry: The Synthesis of Benzopinacol |
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566 | (7) |
| Natural Product Chemistry and Biochemistry |
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64 Carbohydrates and Sweeteners |
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573 | (7) |
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65 Biosynthesis of Ethanol |
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580 | (8) |
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66 Enzymatic Reactions: A Chiral Alcohol from a Ketone and Enzymatic Resolution of DL-Alanine |
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588 | (12) |
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67 Isolation of Lycopene and ß-Carotene |
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600 | (4) |
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68 The Synthesis of Natural Products: Pseudopellitierene and Camphor |
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604 | (10) |
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69 Polymers: Synthesis and Recycling |
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614 | (20) |
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70 Qualitative Organic Analysis |
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634 | (37) |
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71 Searching the Chemical Literature |
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671 | |
| Index |
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