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Details for:
Miller J., Neuzil E. Modern Experimental Organic Chemistry 1982
miller j neuzil e modern experimental organic chemistry 1982
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E-books
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109.3 MB
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Sept. 1, 2023, 3:04 p.m.
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Textbook in PDF format To the Student XVII Laboratory Safety Rules, Procedures, and Equipment XVIII Laboratory Safety Quiz XXIII The Laboratory Notebook XXIV The Laboratory Report: Long Form XXVIII The Laboratory Report: Short Form XXX PART A_ Laboratory Techniques 1 Technique 1 Proper Use of Heating Equipment 2 Technique la Technique 1b Technique Ic Technique Id Technique le Technique If Technique lg Heating with a Bunsen Burner or a Microburner 2 Heating with a Hot Plate 3 Heating with a Heating Mantle 4 Heating with an Oil Bath 5 Heating with a Steam Cone or a Steam Bath 6 Heating with a Hot-water Bath a, Heating with an Infrared Lamp 8 Technique 2. Drying Liquids, Evaporating Liquids, and Using a Magnetic Stirrer 9 Technique 2a Technique 2b Technique 2c Technique 2d Technique 4a Technique 4b Drying Organic Liquids y Evaporation of a Liquid 10 Evaporation Under Reduced Pressure 12 Using a Magnetic Stirrer 14 Technique 3. Heating Under Reflux 16 Technique 4 Separation of Compounds by Distillation 18 Simple Distillation 23 Fractional Distillation 25 Technique 5 Vacuum Distillation 28 Technique 6 Steam Distillation 36 Technique 6a Technique 6b Direct Steam Distillation 39 Live-steam Distillation 40 Technique 7 Thermometer Calibration, Stem Corrections, and Determination of Boiling and Microboiling Points 43 Technique 7a Technique 7b Technique 7c Technique 7d Calibration of a Thermometer 43 Thermometer Stem Corrections 46 Determination of Boiling Point 47 Determination of Microboiling Point 48 Technique 8 Extraction of a Liquid Using a Separatory Funnel 51 Technique 9 Filtration 56 Technique 9a Technique 9b Technique 9c Technique 9d Gravity Filtration 56 Gravity Filtration with Solvent Drying 60 Vacuum Filtration 61 Vacuum Filtration Using a Filter Aid 63 Technique 10 Preparing an Ice Bath 64 Technique 11 Partial Purification with Activated Charcoal 65 Technique 12 Crystallization 66 Technique 12a Technique 12b Crystallization Using Vacuum Filtration 67 Crystallization Using Centrifugal Force 69 Technique 13 Sublimation 72 Technique 14 Melting Point 76 Technique 14a Technique 14b The Melting Point 78 Mixed Melting Points 79 Technique 15 Making Solutions 80 Technique 15a Technique 15b Technique 15c Technique 15d Making a Saturated Solution That Has a Solid Dissolved in a Liquid 80 Making a Percentage-by-weight Solution 81 Making a Percentage-by-volume Solution 81 Making a Molar Solution 82 Technique 16 Proper Label Notation 83 echnique 17a Technique 17b Technique 17c Technique 17d Technique 17e Technique 18 Column Chromatography Technique 18a Technique 18b Technique 18c Technique 18d Technique 19 Gas—Liquid Chromatography Technique 19a Technique 19b Technique 19c Technique 20 Refractometry Technique 20a Technique 20b Technique 21 Polarimetry Technique 21a Technique 21b Technique 22 Recording and Interpreting an Infrared Spectrum Technique 22a Technique 22b Technique 22c Technique 22d Technique 22e Technique 22f Technique 22g Technique 22h Spectra Technique 23a Technique 23b Technique 17 Special Techniques Required in Thin-layer and Paper Chromatography 84 Preparing a Chromatography Tank 85 Preparing a Microscope Slide Thin-layer Plate 87 Preparing a Micropipet and Spotting a Thin-layer or a Paper Chromatogram 88 Running a Chromatogram; Determining R; Values Developing the Chromatogram 91 90 93 Determination of Packing Materials and Solvents for Column Chromatography 94 Packing a Chromatography Column 95 Placing a Compound Mixture to Be Separated on a Column; Eluting Compounds 98 Monitoring Column Chromatography 100 101 Packing a Gas Chromatography Column 103 Running a Gas Chromatogram 103 Analysis of a Gas Chromatogram 106 108 Measuring the Index of Refraction 109 Correcting the Index of Refraction for Temperature 112 113 115 117 Determining Specific Rotation Calculating Optical Purity 119 Interpreting an Infrared Spectrum 123 Preparing a Liquid Sample: Neat (Using Salt Plates) 142 Preparing a Solid Sample Dissolved in a Solvent 143 Preparing a Solid Sample: KBr Pellets 145 Preparing a Solid Sample: Nujol Mull 147 Preparing a Solid Sample: Neat (Using Salt Plates) 148 Calibration of an Infrared Spectrum 149 Operating an Infrared Spectrophotometer 150 Technique 23 Recording and Interpreting Nuclear Magnetic Resonance 151 Analysis of Chemical Shift 156 Analysis of a Spectrum Integration Curve 161 Technique 23c Analysis of Signal Splitting (Spin—Spin Coupling) and the n + 1 Rule 162 Technique 23d Preparation of an nmr Sample 174 Technique 23e Recording an nmr Spectrum 176 Technique 24 Recording and Interpreting an Ultraviolet Spectrum 177 Technique 24a Obtaining a UV Spectrum 185 Technique 24b Interpreting a UV Spectrum 186 Technigue 25 Handling Lithium, Sodium, and Potassium Metal 188 Technique 25a Cutting and Weighing Chunk Sodium or Potassium Metal 189 Technique 25b The Sodium Press and Sodium Wire 190 Technique 25c Lithium Wire 190 PART B_ Introduction to Organic Synthesis Using Fundamental Techniques 191 Experiment 1 Synthesis of Aspirin (Acetylsalicylic Acid) 192 Experiment 2. Synthesis of the Ester Methyl! Salicylate (Oil of Wintergreen) 198 Experiment 3. Synthesis of Isopenty! Acetate (Banana Oil) 203 Experiment 4 Synthesis and Testing of the Allelopathic Agent Juglone 208 Experiment 5 The Formation of Thiokol-A (Synthetic Rubber) 214 Experiment 6 Formation of Ethanol (Alcohol) by Fermentation of Sugar; Identification of Fusel-oil Components in Whiskey and Vodka 217 Experiment 7 Synthesis of Ethyl B-Naphtholate (Nerolin), a Perfume Additive 228 Experiment 8 Synthesis of the Carotenogenesis Inducer 2-Diethylaminoethyl-4-methyloheny! Ether 232 PART C_ Isolation and Purification of Compounds 239 Experiment 9 An Industrial Type of Separation of Crude Oj! and the Identification of Major Components by Gas Chromatography Experiment 10 Isolating Casein, Lactose, and Fats from Dried Milk 245 Experiment 11 Isolating Caffeine from Tea 251 Experiment 12 Isolating Cinnamaldehyde from Cinnamon 260 Experiment 13 Separation of Rosin and Terpenes from Pine Gum and Their Identification 266 Experiment 14 Isolation of a Red Pigment from Paprika 270 Experiment 15 Separating Ricinoleic Acid Methyl Esters from Castor Oil 215 Experiment 16 Isolation and Partial Identification of Components in Clove Oil 283 Experiment 17 Determining the Approximate Amount of Cholesterol, Lecithin, and Fatty Acids in Egg Yolk 289 Experiment 18 Extraction and Comparison of Stereospecific Structures of (+)- and (—)-Carvones from Spearmint Oil and Caraway Seeds 297 Experiment 19 Enzymatic Resolution of D- and L-Methionine 304 Experiment 20 Chemical Resolution of the a-Phenylethylamines 309 PART D- Advanced Organic Synthesis 317 Experiment 21. Hydrogenation of Liquid Oils to Create Fats 318 Experiment 22 Synthesis of 1-Octanol (Octyl Alcohol) and Octy/ Acetate 328 Experiment 23 Synthesis of Two Insect Pheromones, 4-Methyl-3-heptanol and 4-Methy!-3-heptanone 337 Experiment 24 Conversion of Mannose to Mannitol 346 Experiment 25 Synthesis of Benzoic Acid and Testing of Sodium Benzoate 352 Experiment 26 Synthesis of para-Dibromobenzene, a Mothball Analogue 362 Experiment 27 Synthesis of Resacetophenone and Its Use as a Test Reagent for Metal lons 367 Experiment 28 Synthesis and Testing of Methoxychlor and 1,1-Dichloro-2,2'- bis(p-methoxyphenyl)ethene 371 Experiment 29 Synthesis of the Diazo Dye Methyl Orange 380 Experiment 30. Synthesis of a Crown Ether 386 Experiment 31 Synthesis and Testing of Sulfanilamide 393 Experiment 32 Synthesis of Lidocaine, a Local Anesthetic 404 Experiment 33 Synthesis of the Insect Repellent N,N-Diethy/-m-toluamide 414 Experiment 34 Synthesis of Ethyl Acetoacetate, a Primary Biosynthetic Precursor 422 Experiment 35 Synthesis of 2-Heptanone, an insect Pheromone 431 Experiment 36 Synthesis of the Housefly Pheromone (Z)-9-Tricosene 440 Experiment 37. Synthesis of a Nonphysiologically Active Barbiturate 453 Experiment 38 Benzoin Condensation, Benzil, and Synthesis of 5,5-Diphenylhydantoin, an Antiepileptic Drug 463 Experiment 39 Cannizzaro Reaction Forming Furfury! Alcohol and 2-Furoic Acid, with a Practical Application 475 Experiment 40 Diels—Alder Synthesis of an Insecticide Analogue 483 Experiment 41. A Noncarcinogenic Benzidine Rearrangement and a Test for Blood Traces 493 Experiment 42 Synthesis and Comparison of a Soap and a Detergent 500 Experiment 43 Formation of Synthetic Polymers 509 Experiment 44 Conversion of D-Sorbitol to L-Sorbose, a Biological Type of Synthesis 516 Experiment 45 Deducing a Mechanism for the Isomerization of Maleic Acid to Fumaric Acid 521 Experiment 46 The Rate of Hydrolysis of Methy! Acetate 529 PART E_ Identification of Organic Compounds 535 Experiment 47 Identification of F, D, and C Dyes in a Commercial Product (Kool-Aid) 536 Experiment 48 Determining an Appropriate Solvent for the Thin-layer Chromatography of a Brown Dye 541 Experiment 49 Determining the Important Components of Common Nonprescription Analgesics 545 Experiment 50 Identifying Hydrocarbons in Gasoline by Gas Chromatography 550 Experiment 51 Fatty-acid Composition of Commercial Cooking Oils 554 Experiment 52 Tests for Monosaccharides, Disaccharides, and Polysaccharides 563 Section 52a Molisch Test for Carbohydrates 569 Section 52b _Benedict’s Test for Reducing Sugars 571 Section 52c _Barfoed’s Test for Reducing Monosaccharides 573 Section 52d __ Bial’s Test for Pentoses 574 Section 52e Seliwanoff’s Test for Ketoses 575 Section 52f Tes-Tape Test for Glucose 577 Section 52g Mucic Acid Test for Galactose 578 Section 52h —lodine—Starch Test 579 Section 521 Hydrolysis of Sucrose, Lactose, and Maltose 579 Section 52} | Hydrolysis of Starch 580 Section 52k Semicarbazone Test 581 Section 521 Determination of an Unknown (Optional) 582 Experiment 53 Testing Urine for Possible Pathological Conditions 584 Experiment 54 Analysis of Commercial Samples of Aspirin by Ultraviolet Spectroscopy 590 PART F Determination of the Structure of Organic Compounds 595 Experiment 55 Analyses of a Compound'’s Structure 596 Section 55a Observations and Physical Measurements 598 Section 55b Elemental Analysis 608 Section 55c Spectroscopic Analysis 615 Section 55d Analysis for Double and Triple Bonds 616 Section 55e Analysis for Aromatic Rings 619 Section 55f Analysis of Aldehydes and Ketones 621 Section 55g Analysis of Carboxylic Acids 632 Section 55h Analysis of Phenols 635 Section 551 Analysis of Alcohols 641 Section 55; Analysis of Amines 649 Section 55k Analysis of Esters 656 Section 551 Analysis of Nitro Compounds 661 Section 55m _ Analysis of Alkyl and Aryl Halides 664 Experiment 56 Assignment of Structure to a- and B-D-Glucose Pentaacetate by Nuclear Magnetic Resonance 670 Experiment 57 Determination of Keto—Enol Tautomerism Using Nuclear Magnetic Resonance 680 Experiment 58 Searching the Chemical Literature 686 Index 715
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Miller J., Neuzil E. Modern Experimental Organic Chemistry 1982.pdf
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