Techniques and Experiments for Organic Chemistry

, by Ault, Addison

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ISBN: 9780935702767 | 0935702768
Cover: Hardcover
Copyright: 6/1/1998

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Supplemental Materials

Preface to the Sixth Edition

xix

(2)

Preface to the Fifth Edition

xxi

PART I Laboratory Operations

(324)

Preliminary Topics

1. Safety

(13)

1.1 Fire

(1)

1.2 Explosions

(1)

1.3 Poisoning

(1)

1.4 Cuts

(1)

1.5 Spills

(1)

1.6 Chemicals in the Eye

(1)

1.7 A Short List of Hazardous Materials and Some of Their Properties

(8)

2. Glassware Used in the Organic Chemistry Laboratory

(5)

3. Cleaning Up

(3)

3.1 Care of Ground-Glass-Jointed Glassware

(1)

3.2 Separatory Funnels and Glassware with Stopcocks

(1)

3.3 Drying of Glassware

(1)

4. Collection and Disposal of Waste

(2)

4.1 Solid Waste

(1)

4.2 Liquid Waste

(1)

4.3 General Instructions for Collection of Waste

(1)

5. The Laboratory Notebook

(5)

6. The Chemical Literature

(7)

6.1 Secondary Sources for Physical Properties of Organic Compounds

(3)

6.2 Secondary Sources for Methods of Preparation of Organic Compounds

(1)

6.3 Collection of Spectra

(1)

6.4 Miscellaneous

(1)

7. Tables

(6)

7.1 Solutions of Acids

(1)

7.2 Solutions of Bases

(1)

7.3 Molecular Weights and Molar Volumes of Acids

(1)

7.4 Molar Weights of Bases

(1)

7.5 Molecular Weights, Densities, and Molar Volumes of Selected Liquid Reagents

(1)

7.6 Periodic Table of the Elements

(2)

Separation of Substances; Purification of Substances

8. Filtration

(4)

8.1 Gravity Filtration

(1)

8.2 Micro-Scale Gravity Filtration

(1)

8.3 Vacuum or Suction Filtration

(3)

9. Recrystallization

(14)

9.1 Choice of Solvent

(1)

9.2 Dissolving the Sample

(1)

9.3 Decolorizing the Solution

(1)

9.4 Hot Filtration

(2)

9.5 Cooling for Crystallization

(1)

9.6 Cold Filtration

(1)

9.7 Washing the Crystals

(1)

9.8 Drying the Crystals

(1)

9.9 More Techniques of Crystallization

(2)

9.10 Micro-Scale Recrystallization

(2)

9.11 Selection of a Suitable Solvent

(3)

10. Distillation

(18)

10.1 Vapor Pressure

(3)

10.2 Distillation of a Pure Liquid

(1)

10.3 Miscible Pairs of Liquids

(3)

10.4 Fractional Distillation

(2)

10.5 Azotropic Mixtures

(3)

10.6 Technique of Distillation

(2)

10.7 Small-Scale Distillation

(3)

11. Reduced-Pressure Distillation

(7)

11.1 Estimation of the Boiling Point at Reduced Pressure

(1)

11.2 Apparatus

(1)

11.3 Source of Vacuum

(1)

11.4 Pressure Measurement

(1)

11.5 Technique of Distillation Under Reduced Pressure

(2)

12. Distillation of Mixtures of Two Immiscible Liquids; Steam Distillation

(3)

12.1 Theory of Steam Distillation

(1)

12.2 Technique of Steam Distillation

(2)

13. Sublimation

(2)

13.1 Theory of Sublimation

(1)

13.2 Technique of Sublimation

(1)

14. Extraction by Solvents

(17)

14.1 Theory of Extraction

(2)

14.2 Extraction of Acids and Bases

(3)

14.3 Technique of Extraction

(4)

14.4 Micro-Scale Extraction

101

(8)

15. Chromatography

109

(20)

15.1 Theory of Column Chromatography

110

(3)

15.2 Technique of Column Chromatography

113

(3)

15.3 Theory of Thin-Layer Chromatography

116

(2)

15.4 Technique of Thin-Layer Chromatography

118

(2)

15.5 Theory of Paper Chromatography

120

(1)

15.6 Technique of Paper Chromatography

120

(2)

15.7 Theory of Vapor-Phase Chromatography

122

(4)

15.8 Technique of Vapor-Phase Chromatography

126

(2)

15.9 High-Pressure Liquid Chromatography

128

(1)

15.10 Batchwise Adsorption; Decolorization

129

(1)

16. Removal of Water; Drying

129

(9)

16.1 Drying of Solids

130

(2)

16.2 Drying of Solutions

132

(2)

16.3 Drying of Solvents and Liquid Reagents

134

(4)

Determination of Physical Properties

17. Boiling Point

138

(12)

17.1 Experimental Determination of Boiling Point

138

(3)

17.2 Boiling Point and Molecular Structure

141

(3)

17.3 Boiling Point and the Enthalpy and Entropy of Vaporization

144

(6)

18. Melting Point

150

(9)

18.1 Experimental Determination of the Melting Point

150

(4)

18.2 The Melting Point as a Criterion of Purity

154

(1)

18.3 The Melting Point as a Means of Identification and Characterization

155

(1)

18.4 Mixture Melting Points

155

(1)

18.5 Melting Point and Molecular Structure

155

(4)

19. Density; Specific Gravity

159

(2)

19.1 Experimental Determination of the Density

159

(1)

19.2 Density and Molecular Structure

160

(1)

20. Index of Refraction

161

(2)

20.1 Experimental Determination of the Index of Refraction

161

(1)

20.2 Index of Refraction and Molecular Structure

162

(1)

21. Optical Activity

163

(5)

21.1 Experimental Determination of Optical Rotation

163

(3)

21.2 Optical Activity and Molecular Structure

166

(2)

22. Molecular Weight

168

(1)

22.1 Molecular Weight Determination by Mass Spectrometry

168

(1)

22.2 Molecular Weight Determination by Other Methods

169

(1)

23. Solubility

169

(13)

23.1 Solubility of Liquids in Liquids

170

(4)

23.2 Solubility of Solids in Liquids

174

(1)

23.3 Classification of Compounds by Solubility; Relationships Between Solubility and Molecular Structure

175

(5)

23.4 Techniques for Determination of Solubility

180

(2)

24. Infrared Absorption Spectrometry

182

(19)

24.1 Wavelength, Frequency, and Energy of Electromagnetic Radiation

183

(1)

24.2 Units of Light Absorption

183

(2)

24.3 Infrared Light Absorption and Molecular Structure

185

(1)

24.4 Interpretation of Infrared Spectra

186

(5)

24.5 Sample Preparation

191

(10)

25. Ultraviolet-Visible Absorption Spectrometry

201

(6)

25.1 Ultraviolet-Visible Light Absorption and Molecular Structure

202

(1)

25.2 Interpretation of Ultraviolet-Visible Spectra

203

(1)

25.3 Color and Molecular Structure

203

(1)

25.4 Sample Preparation

204

(3)

26. Nuclear Magnetic Resonance Spectrometry

207

(24)

26.1 Shielding; Chemical Shift

208

(3)

26.2 Splitting

211

(8)

26.3 The Integral

219

(1)

26.4 Nuclear Magnetic Resonance and Molecular Structure

220

(2)

26.5 Interpretation of NMR Spectra

222

(4)

26.6 Sample Preparation

226

(5)

27. Mass Spectrometry

231

(10)

27.1 Theory of Mass Spectrometry

231

(3)

27.2 Interpretation of Mass Spectra

234

(2)

27.3 High-Resolution Mass Spectrometry

236

(5)

Determination of Chemical Properties: Qualitative Organic Analysis

28. Qualitative Tests for the Elements

241

(6)

28.1 Ignition Test; Test for Metals

241

(1)

28.2 Beilstein Test; Test for Halogens (Except Fluorine)

242

(1)

28.3 Sodium Fusion Test; Test for Nitrogen, Sulfur, and the Halogens

242

(5)

29. Qualitative Characterization Tests: Tests for the Functional Groups

247

(19)

29.1 Detection of Ammonia from Ammonium Salts, Primary Amides, and Nitriles

249

(1)

29.2 Benzenesulfonyl Chloride (Hinsberg's Test)

250

(2)

29.3 Bromine in Carbon Tetrachloride

252

(1)

29.4 Chromic Anhydride

253

(1)

29.5 2,4-Dinitrophenylhydrazine

253

(1)

29.6 Ferric Chloride Solution

254

(1)

29.7 Ferric Hydroxamate Test

255

(3)

29.8 Hydrochloric Acid/Zinc Chloride Test (Lucas's Test)

258

(1)

29.9 Iodoform Test

258

(2)

29.10 Aqueous Potassium Permanganate Solution (Baeyer's Test)

260

(1)

29.11 Alcoholic Silver Nitrate Solution

261

(1)

29.12 Sodium Hydroxide Test

262

(1)

29.13 Sodium Iodide in Acetone

263

(1)

29.14 Tollen's Reagent: Silver-Ammonia Complex Ion

263

(3)

30. Characterization Through Formation of Derivatives

266

(33)

30.1 Benzoates, p-Nitrobenzoates, and 3,5-Dinitrobenzoates of Alcohols

272

(1)

30.2 Hydrogen 3-Nitrophthalates of Alcohols

273

(1)

30.3 Phenyl-and Alpha-Naphthylurethans

274

(1)

30.4 Methone Derivations of Aldehydes

274

(1)

30.5 2,4-Dinitrophenylhydrazones

275

(1)

30.6 Semicarbazones

276

(1)

30.7 Oximes

276

(1)

30.8 Carboxylic Acids by Hydrolysis of Primary Amides and Nitriles

277

(1)

30.9 9-Acylamidoxanthenes from Amides

278

(1)

30.10 Hydrolysis of N-Substituted Amides

279

(1)

30.11 Substituted Acetamides from Amines

280

(1)

30.12 Substituted Benzamides from Amines

281

(1)

30.13 p-Toluenesulfonamides from Amines

282

(1)

30.14 Phenylthioureas and Alpha-Naphthylthioureas

282

(1)

30.15 Picrates

283

(2)

30.16 Quaternary Ammonium Salts: Methiodides and p-Toluenesulfonates

285

(1)

30.17 Carboxylic Acid Amides

285

(1)

30.18 Anilides, p-Toluidides, and p-Bromoanilides of Carboxylic Acids

286

(1)

30.19 Phenacyl and Substituted Phenacyl Esters of Carboxylic Acids

287

(2)

30.20 P-Nitrobenzyl Esters of Carboxylic Acids

289

(1)

30.21 N-Benzylamides from Esters

290

(1)

30.22 3,5-Dinitrobenzoates from Esters

290

(1)

30.23 Hydrolysis of Esters

291

(1)

30.24 Bromination of Aromatic Ethers

292

(1)

30.25 S-Alkylthiuronium Picrates

293

(1)

30.26 o-Aroylbenzoic Acids from Aromatic Hydrocarbons

294

(1)

30.27 Aromatic Acids by Oxidation by Permanganate

295

(1)

30.28 Anilides, p-Toluidides, and Alpha-Naphthalides from Alkyl Halides

295

(1)

30.29 2,4,7-Trinitrofluorenone Adducts of Aromatic Hydrocarbons

296

(1)

30.30 Bromination of Phenols

297

(1)

30.31 Aryloxyacetic Acids from Phenols

297

(2)

Apparatus and Techniques for Chemical Reactions

31. Assembling the Apparatus

299

(3)

32. Temperature Control

302

(3)

33. Methods of Heating and Cooling

305

(5)

33.1 Heating

305

(4)

33.2 Cooling

309

(1)

34. Stirring

310

(3)

35. Addition of Reagents

313

(2)

36. Control of Evolved Gases

315

(2)

37. Concentration; Evaporation

317

(1)

38. Use of an Inert Atmosphere

318

(1)

39. Working Up the Reaction; Isolation of the Product

319

(8)

PART II Experiments

327

(308)

Isolations and Purifications

E1 Isolation of Cholesterol from Gallstones

327

(2)

E2 Isolation of Lactose from Powdered Milk

329

(3)

E3 Isolation of Acetylsalicylic Acid from Aspirin Tablets

332

(3)

E4 Isolation of Ibuprofen from Ibuprofen Tablets

335

(2)

E5 Isolation of Caffeine from Tea and NoDoz

337

(3)

E6 Isolation of Piperine from Black Pepper

340

(2)

E7 Isolation of Trimyristin from Nutmeg

342

(2)

E8 Isolation of Clove Oil from Cloves

344

(2)

E9 Isolation of Eugenol from Clove Oil

346

(1)

E10 Isolation of (R)-(+)-Limonene from Grapefruit or Orange Peel

347

(3)

E11 Isolation of (R)-(-)-or (S)-(+)-Carvone from Oil of Spearmint or Oil of Caraway

350

(5)

E12 Resolution of Alpha-Phenylethylamine by (R),(R)-(+)-Tartaric acid

355

(8)

Transformations

Isomerizations

363

(8)

E13 Adamantane from endo-Tetrahydrodicyclopentadiene via the Thiourea Clathrate

364

(3)

E14 cis-Dibenzoylethyelene from trans-1,2-Dibenzoylethylene

367

(4)

Preparation of Cyclohexanol

371

(4)

E15 Cyclohexanol from Cyclohexene

371

(2)

E16 Cycohexanol from Cyclohexanone

373

(2)

Reactions of Cyclohexanol

375

(14)

E17 Cyclohexene from Cyclohexanol

376

(5)

E18 Dehydration of 2-Methylcyclohexanol: A Variation

381

(3)

E19 Cyclohexyl Bromide from Cyclohexanol

384

(3)

E20 Cyclohexanone from Cyclohexanol

387

(2)

Addition of Dichlorcarbene to Alkenes by Phase Transfer Catalysis

389

(8)

E21 Addition of Dichlorocarbene to Cyclohexene

392

(2)

E22 Addition of Dichlorocarbene to Styrene: A Variation

394

(2)

E23 Addition of Dichlorocarbene to 1,5-Cycloctadiene: Another Variation

395

(2)

Alkyl Halides from Alcohols

397

(20)

E24 Isoamyl Bromide from Isoamyl Alcohol

398

(4)

E25 n-Butyl Bromide from n-Butyl Alcohol: A Variation

402

(1)

E26 tert-Butyl Chloride from tert-Butyl Alcohol

403

(3)

E27 tert-Amyl Chloride from tert-Amyl Alcohol: A Variation

406

(1)

E28 Competitive Nucleophilic Substitution of Butyl Alcohols by Bromide and Chloride Ion

407

(3)

E29 Kinetics of the Hydrolysis of tert-Butyl Chloride

410

(7)

Isoamyl Acetate: A Component of the Alarm Pheromone of the Honey Bee

417

(10)

E30 Isoamyl Acetate from Isoamyl Bromide and Potassium Acetate

421

(3)

E31 Isoamyl Acetate from Isoamyl Alcohol and Acetic Acid; The Fischer Estrification

424

(3)

Liquid Crystals

427

(4)

E32 Cholesteryl Benzoate from Cholesterol

428

(3)

Acetylation of Glucose

431

(8)

E33 Alpha-D-Glucose Pentaacetate from Glucose

433

(1)

E34 Beta-D-Glucose Pentaacetate from Glucose

433

(1)

E35 Acetylation of Glucose in N-Methylimidazole: A Variation

434

(2)

E36 Preparation of Methyl Benzoate, Oil of Niobe

436

(3)

The Grignard Reaction

439

(5)

E37 Aliphatic Alcohols: Preparation by Grignard Synthesis

439

(5)

Preparation of Triphenylmethanol

444

(12)

E38 Preparation of Triphenylmethanol from Benzophenone

446

(2)

E39 Preparation of Triphenylmethanol from Methyl Benzoate

448

(3)

E40 Preparation of Triphenylmethanol from Dimethyl Carbonate

451

(3)

E41 Preparation of Aniline from Nitrobenzene

454

(2)

Preparation of Amides

456

(7)

E42 Acetanilide from Aniline

457

(4)

E43 N,N-Diethyl-m-Toluamide from m-Toluic Acid; A Mosquito Repellant: "Off"

461

(2)

Electrophilic Substitution Reactions of Benzene Derivatives

463

(9)

E44 Methyl m-Nitrobenzoate from Methyl Benzoate

464

(2)

E45 p-Bromoacetanilide from Acetanilide

466

(3)

E46 2,4-Dinitrobromobenzene from Bromobenzene

469

(3)

Nucleophilic Aromatic Substitution Reactions of 2,4-Dinitrobromobenzene

472

(8)

E47 2,4-Dinitroaniline

473

(1)

E48 2,4-Dinitrophenylhydrazine

474

(1)

E49 2,4-Dinitrodiphenylamine

475

(2)

E50 2,4-Dinitrophenylpiperidine

477

(1)

E51 4-Substituted 2,4-Dinitrophenylanilines: A Variation

478

(2)

Diazonium Salts of Aromatic Amines

480

(2)

E52 Benzenediazonium Chloride from Aniline

481

(1)

E53 p-Nitrobenzenediazonium Sulfate from p-Nitroaniline

482

(1)

Replacement Reactions of Diazonium Salts

482

(3)

E54 Chlorobenzene from Benzenediazonium Chloride

483

(2)

Reactions of Vanillin

485

(13)

E55 Acetylvanillin from Vanillin

486

(1)

E56 5-Bromovanillin from Vanillin

487

(2)

E57 5-Nitrovanillin from Vanillin

489

(1)

E58 Vanillin Oxime from Vanillin

490

(1)

E59 Vanillin Semicarbazone from Vanillin

491

(2)

E60 Vanillyl Alcohol from Vanillin

493

(1)

E61 Vanillideneacetone from Vanillin

494

(4)

Synthesis of Dyes

498

(9)

E62 Benzenediazonium Chloride and Beta-Naphthol: 1-Phenylazo-2-Naphthol (Sudan I)

499

(3)

E63 p-Nitrobenzenediazonium Sulfate and Phenol: p-(4-nitrobenzeneazo)-phenol

502

(1)

E64 p-Nitrobenzenediazonium Sulfate and Beta-Naphthol: 1-(p-nitrophenylazo)-2-naphthol (Para Red; American Flag Red)

503

(2)

E65 p-Nitrobenzenediazonium Sulfate and Dimethylaniline: p-(4-nitrobenzeneazo)-N,N-Dimethylaniline

505

(2)

The Diels-Alder Reaction

507

(10)

E66 Butadiene (from 3-Sulfolene) and Maleic Anhydride

508

(2)

E67 Cyclopentadiene and Maleic Anhydride

510

(4)

E68 Furan and Maleic Anhydride

514

(1)

E69 Alpha-Phellandrene and Maleic Anhydride

515

(2)

The Writing Reaction

517

(10)

E70 The Preparation of trans-Stilbene

519

(5)

E71 Preparation of trans, trans-1, 4-Diphenylbutadiene: A Variation

524

(3)

Analgesics: Aspirin, Phenacetin, and Tylenol

527

(9)

E72 Acetylsalicylic Acid from Salicylic Acid: Preparation of Aspirin

527

(2)

E73 p-Acetamidophenol from p-Aminophenol: Preparation of Tylenol

529

(2)

E74 p-Ethoxyacetanilide from p-Ethoxyaniline: Preparation of Phenacetin

531

(4)

E75 p-Ethoxyacetanilide from p-Acetamidophenol: Another Preparation of Phenacetin

535

(1)

Nitration of Phenacetin

536

(2)

E76 2-Nitrophenacetin form Phenacetin

536

(2)

Esterification of Salicylic Acid

538

(2)

E77 Preparation of Methyl Salicylate: Oil of Wintergreen

538

(2)

Coconut Aldehyde; Gamma-Nonanolactone

540

(6)

E78 3-Nonenoic Acid from Heptaldehyde and Malonic Acid

541

(2)

E79 Coconut Aldehyde from 3-Nonenoic Acid

543

(4)

Catalysis by Thiamine

546

(6)

E80 Thiamine-Catalyzed Formation of Benzoin from Benzaldehyde

546

(6)

A Model for the Reducing Agent NADH

552

(7)

E81 1-Benzylnicotinamide Chloride from Nicotinamide

554

(2)

E82 1-Benzyldihydronicotinamide form 1-Benzylnicotinamide Chloride

556

(1)

E83 Reduction of Malachite Green by 1-Benzyl-dihydronicotinamide

557

(2)

Two Thermochronic Compounds

559

(5)

E84 Dixanthylene from Xanthone

560

(1)

E85 Dianthroquinone from Anthrone via 9-Bromoanthrone

561

(3)

A Photochromic Compound: 2-(2, 4-Dinitrobenzyl) pyridine

564

(14)

E86 A Photochromic Compound: 2-(2, 4-Dinitrobenzyl) pyridine

564

(3)

E87 A Chemiluminescent Compound: Luminol

567

(11)

Synthetic Sequences: Experiments that Use a Sequence of Reactions

Steroid Transformations

578

(11)

E88 Cholesterol Dibromide from Cholesterol

580

(2)

E89 5Alpha, 6Beta-Dibromocholestane-3-one from Cholesterol Dibromide

582

(1)

E90 Delta5-Cholestene-3-one from 5Alpha, 6Beta-Dibromocholestane-3-one

583

(4)

E91 Delta4-Cholestene-3-one from Delta5-Cholestene-3-one

587

(2)

Tetraphenylcyclopentadienone: A Purple Compound

589

(8)

E92 Benzoin from Benzaldehyde

591

(1)

E93 Benzil from Benzoin

592

(1)

E94 Dibenzylketone from Phenylacetic Acid

593

(2)

E95 Tetraphenylcyclopentadienone form Benzil and Dibenzyl Ketone

595

(2)

Sulfanilamide

597

(10)

E96 p-Acetamidobenzenesulfonyl Chloride from Acetanilide

602

(2)

E97 p-Acetamidobenzenesulfonamide from p-Acetamidobenzenesulfonyl Chloride

604

(1)

E98 Sulfanilamide from p-Acetamidobenzenesulfonamide

605

(2)

A Bootstrap Synthesis: p-Phenetidine from p-Phenetidine

607

(8)

E99 Ethyldioxyazobenzene from p-Phenetidine

608

(2)

E100 Diethyldioxyazobenzene from Ethyldioxyazobenzene

610

(1)

E101 p-Phenetidine from Diethyldioxyazobenzene

611

(4)

1-Bromo-3-Chloro-5-iodobenzene

615

(12)

E102 2-Chloro-4-Bromoacetanilide from 4-Bromoacetanilide

617

(3)

E103 2-Chloro-4-Bromoaniline from 2-Chloro-4-Bromoacetanilide

620

(2)

E104 2-Chloro-4-Bromo-6-iodoaniline from 2-Chloro-4-Bromoaniline

622

(2)

E105 1-Bromo-3-chloro-5-Iodobenzene from 2-Chloro-4-bromo-6-iodoaniline

624

(3)

MOED: A Merocyanine Dye

627

(8)

E106 1,4-Dimethylpyridinium Iodide from 4-Methylpyridine and Methyl Iodide

629

(1)

E107 Preparation of 4-(p-Hydroxystyryl)-1-Methylpyridinium Iodide from 1-4-Dimethylpyridinium Iodide and p-Hydroxybenzaldehyde

630

(2)

E108 1-Methyl-4 [(Oxocyclohexadienylidene)-Ethylidene]-1, 4-Dihydropyridine (MOED) from 4-(p-Hydroxystyryl)-1-Methyl-pyridinium Iodide

632

(3)

Appendix

635

(12)

Chemical Substance Index

647

(8)

General Subject Index

655

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