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Techniques and Experiments for Organic Chemistry SIXTH EDITION

Addison Ault Cornell College

4>

University Science Books Sausalito, California

Contents Preface to the Sixth Edition

xix

Preface to the Fifth Edition

xxi

PART

I

Laboratory Operations

Preliminary Topics 1. Safety 1.1 1.2 1.3 1.4 1.5 1.6 1.7

2. 3.

4.

5.

Fire Explosions Poisoning Cuts Spills Chemicals in the Eye A Short List of Hazardous Materials and Some of Their Properties Glassware Used in the Organic Chemistry Laboratory Cleaning Up 3.1 Care of Ground-Glass-Jointed Glassware 3.2 Separatory Funnels and Glassware with Stopcocks 3.3 Drying of Glassware Collection and Disposal of Waste 4.1 Solid Waste 4.2 Liquid Waste 4.3 General Instructions for Collection of Waste The Laboratory Notebook

6. The Chemical Literature 6.1 Secondary Sources for Physical Properties of Organic Compounds 6.2 Secondary Sources for Methods of Preparation of Organic Compounds 6.3 Collections of Spectra 6.4 Miscellaneous

3 4 5 6 7 7 8 8 16 21 22 23 23 24 24 25 25 26 31 32 35 36 37

vi Contents Tables 7.1 Solutions of Acids 7.2 Solutions of Bases 7.3 Molecular Weights and Molar Volumes of Acids 7.4 Molar Weights of Bases 7.5 Molecular Weights, Densities, and Molar Volumes of Selected Liquid Reagents 7.6 Periodic Table of the Elements

38 39 40 40 41 41 42

Separation of Substances; Purification of Substances 8. Filtration 8.1 Gravity Filtration 8.2 Micro-Scale Gravity Filtration 8.3 Vacuum or Suction Filtration

44 44 45 45

9. Recrystallization 9.1 Choiceof Solvent 9.2 Dissolving the Sample 9.3 Decolorizing the Solution 9.4 Hot Filtration 9.5 Cooling for Crystallization 9.6 Cold Filtration 9.7 Washing the Crystals 9.8 Drying the Crystals 9.9 More Techniques of Crystallization 9.10 Micro-Scale Recrystallization 9.11 Selection ofaSuitable Solvent

48 49 49 50 50 52 53 53 54 55 57 59

10. Distillation 10.1 Vapor Pressure 10.2 Distillation of a Pure Liquid 10.3 Miscible Pairs of Liquids 10.4 Fractional Distillation 10.5 Azotropic Mixtures 10.6 Technique of Distillation 10.7 Small-Scale Distillation

62 63 66 67 70 72 75 77

11. Reduced-Pressure Distillation 11.1 Estimation of the Boiling Point at Reduced Pressure 11.2 Apparatus

80 81 82

Contents 11.3 Source of Vacuum 11.4 Pressure Measurement 11.5 Technique of Distillation Under Reduced Pressure

83 84 85

12. Distillation of Mixtures of Two Immiscible Liquids; Steam Distillation 12.1 Theory of Steam Distillation 12.2 Technique of Steam Distillation

87 87 88

13. Sublimation 13.1 Theory of Sublimation 13.2 Technique of Sublimation

90 90 91

14. Extraction by Solvents 14.1 Theory of Extraction 14.2 Extraction ofAcids and Bases 14.3 Technique of Extraction 14.4 Micro-Scale Extraction 15. Chromatography 15.1 Theory of Column Chromatography 15.2 Technique of Column Chromatography 15.3 Theory ofThin-Layer Chromatography 15.4 Technique ofThin-Layer Chromatography 15.5 Theory of Paper Chromatography 15.6 Technique of Paper Chromatography 15.7 Theory ofVapor-Phase Chromatography 15.8 Technique ofVapor-Phase Chromatography 15.9 High-Pressure Liquid Chromatography 15.10 Batchwise Adsorption; Decolorization

92 92 94 97 101 109 110 113 116 118 120 120 122 126 128 129

16. Removal of Water; Drying 16.1 Drying of Solids 16.2 Drying of Solutions 16.3 Drying of Solvents and Liquid Reagents

129 130 132 134

Determination of Physical Properties 17. Boiling Point 17.1 Experimental Determination of Boiling Point 17.2 Boiling Point and Molecular Structure 17.3 Boiling Point and the Enthalpy and Entropy of Vaporization

138 138 141 144

vii

18. Melting Point 18.1 Experimental Determination of the Melting Point 18.2 The Melting Point as a Criterion of Purity 18.3 The Melting Point as a Means of Identification and Characterization 18.4 Mixture Melting Points 18.5 Melting Point and Molecular Structure 19. Density; Specific Gravity 19.1 Experimental Determination of the Density 19.2 Density and Molecular Structure 20. Index ofRefraction 20.1 Experimental Determination of the Index ofRefraction 20.2 Index ofRefraction and Molecular Structure 21. Optical Activity 21.1 Experimental Determination of Optical Rotation 21.2 Optical Activity and Molecular Structure 22. Molecular Weight 22.1 Molecular Weight Determination by Mass Spectrometry 22.2 Molecular Weight Determination byOtherMethods 23. Solubility 23.1 Solubility of Liquids in Liquids 23.2 Solubility of Solids in Liquids 23.3 Classification of Compounds by Solubility; Relationships Between Solubility and Molecular Structure 23.4 Techniques for Determination of Solubility 24. Infrared Absorption Spectrometry 24.1 Wavelength, Frequency, and Energy of Electromagnetic Radiation 24.2 Units of Light Absorption 24.3 InfraredLight Absorption and Molecular Structure 24.4 Interpretation of Infrared Spectra 24.5 Sample Preparation 25. Ultraviolet-Visible Absorption Spectrometry 25.1 Ultraviolet-Visible Light Absorption and Molecular Structure 25.2 Interpretation of Ultraviolet-Visible Spectra 25.3 Color and Molecular Structure 25.4 Sample Preparation

150 150 154 155 155 155 159 159 160 161 161 162 163 163 166 168 168 169 169 170 174

175 180 182 183 183 185 186 191 201 202 203 203 204

Contents Nuclear Magnetic Resonance Spectrometry 26.1 Shielding; Chemical Shift Splitting 26.2 26.3 The Integral 26.4 Nuclear Magnetic Resonance and Molecular Structure 26.5 Interpretation of NMR Spectra 26.6 Sample Preparation Mass Spectrometry 27.1 Theory of Mass Spectrometry 27.2 Interpretation of Mass Spectra 27.3 High-Resolution Mass Spectrometry

207 208 211 219 220 222 226 231 231 234 236

Determination of Chemical Properties: Qualitative Organic Analysis 28. Qualitative Tests for the Elements 28.1 Ignition Test; Test for Metals 28.2 Beilstein Test; Test for Halogens (Except Fluorine) 28.3 Sodium Fusion Test; Test for Nitrogen, Sulfur, and the Halogens 29. Qualitative Characterization Tests: Tests for the Functional Groups 29.1 Detection of Ammonia from Ammonium Salts, Primary Amides, and Nitriles 29.2 Benzenesulfonyl Chloride (Hinsberg's Test) 29.3 Bromine in Carbon Tetrachloride 29.4 Chromic Anhydride 29.5 2,4-Dinitrophenylhydrazine 29.6 Ferric Chloride Solution 29.7 Ferric Hydroxamate Test 29.8 Hydrochloric Acid/Zinc Chloride Test (Lucas's Test) 29.9 Iodoform Test 29.10 Aqueous Potassium Permanganate Solution (Baeyer's Test) 29.11 Alcoholic Silver Nitrate Solution 29.12 Sodium Hydroxide Test 29.13 Sodium Iodide in Acetone 29.14 Tollen's Reagent: Silver-Ammonia Complex Ion

241 241 242 242 247 249 250 252 253 253 254 255 258 258 260 261 262 263 263

ix

x

Contents 30. Characterization Through Formation of Derivatives 30.1 Benzoates, jb-Nitrobenzoates, and 3,5-Dinitrobenzoates of Alcohols 30.2 Hydrogen 3-Nitrophthalates of Alcohols 30.3 Phenyl-and a-Naphthylurethans 30.4 Methone Derivations ofAldehydes 30.5 2,4-Dinitrophenylhydrazones 30.6 Semicarbazones 30.7 Oximes 30.8 Carboxylic Acids by Hydrolysis of Primary Amides and Nitriles 30.9 9-Acylamidoxanthenes from Amides 30.10 Hydrolysis of N-Substituted Amides 30.11 Substituted Acetamides from Amines 30.12 Substituted Benzamides from Amines 30.13 /i-Toluenesulfonamides from Amines 30.14 Phenylthioureas and a-Naphthylthioureas 30.15 Picrates 30.16 Quaternary Ammonium Salts: Methiodides and /»-Toluenesulfonates 30.17 Carboxylic Acid Amides 30.18 Anilides, jb-Toluidides, and jb-Bromoanilides of Carboxylic Acids 30.19 Phenacyl and Substituted Phenacyl Esters of Carboxylic Acids 30.20 jö-Nitrobenzyl Esters of Carboxylic Acids 30.21 N-Benzylamides from Esters 30.22 3,5-Dinitrobenzoates from Esters 30.23 Hydrolysis of Esters 30.24 Bromination of Aromatic Ethers 30.25 S-Alkylthiuronium Picrates 30.26 o-Aroylbenzoic Acids from Aromatic Hydrocarbons 30.27 Aromatic Acids by Oxidation by Permanganate 30.28 Anilides, /»-Toluidides, and a-Naphthalides from Alkyl Halides 30.29 2,4,7-Trinitrofluorenone Adducts of Aromatic Hydrocarbons 30.30 Bromination of Phenols 30.31 Aryloxyacetic Acids from Phenols

266 272 273 274 274 275 276 276 277 278 279 280 281 282 282 283 285 285 286 287 289 290 290 291 292 293 294 295 295 296 297 297

Apparatus and Techniques for Chemical Reactions 31. Assembling the Apparatus 32. Temperature Control 33. Methods of Heating and Cooling 33.1 Heating 33.2 Cooling 34. Stirring 35. Addition of Reagents 36. Control of Evolved Gases 37. Concentration; Evaporation 38. Use of an Inert Atmosphere 39. Working Up the Reaction; Isolation of the Product

PART

II

299 302 305 305 309 310 313 315 317 318 319

Experiments

Isolations and Purifications El E2 E3 E4 E5 E6 E7 E8 E9 E10 Ell El2

Isolation of Cholesterol from Gallstones Isolation ofLactose from Powdered Milk Isolation of Acetylsalicylic Arid from Aspirin Tablets Isolation of Ibuprofen from Ibuprofen Tablets Isolation of Caffeine from Tea and NoDoz Isolation of Piperine from Black Pepper Isolation of Trimyristin from Nutmeg Isolation of Clove Oil from Cloves Isolation ofEugenol from Clove Oil Isolation of (R)-(+)-Limonene from Grapefruit or Orange Peel Isolation of (R)-(-)-or (S)-(+)-Carvone from Oil of Spearmint or Oil of Caraway Resolution of a-Phenylethylamine by (R),(R)-(+)-Tartaricarid

327 329 332 335 337 340 342 344 346 347 350 355

Transformations Isomerizations E13 Adaman tane frora tfwdo-Tetrahydrodicyclopentadiene via the Thiourea Clathrate El4 os-Dibenzoylethyelene from

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