《Laboratory experiments in organic chemistry》

Experiments on Separation and Purification1

Introduction3

1.Simple Distillation19

EXPERIMENT 137

2.Fractional Distillation40

EXPERIMENT 250

3.Vacuum Distillation54

EXPERIMENT 362

4.Steam Distillation64

EXPERIMENT 471

5.Melting Points74

EXPERIMENT 584

6.Crystallization and Sublimation86

EXPERIMENT 698

7.Extraction with Solvents102

EXPERIMENT 7112

8.Chromatography117

EXPERIMENT 8136

9.Accessory Laboratory Operations141

Preparation and Reactions of Typical Organic Compounds151

General Remarks153

Experiment162

10.Hydrocarbons162

11.Alkenes170

12.Alkyl Halides178

13.Biosynthesis of Alcohols186

14.Reactions of Alcohols192

15.A Multiple-Step Synthesis200

16.Aldehydes and Ketones207

17.Reactions of Aldehydes and Ketones217

18.Esters227

19.Acid Amides238

20.Sugars:Monosaccharides and Disaccharides247

21.Friedel-Crafts Reactions253

22.Nitration of Aromatic Compounds264

23.Sulfonation of Aromatic Compounds270

24.Side Chain Oxidation of Aromatic Compounds275

25.Phenols278

26.Reactions of Amines285

27.A Multiple-Step Sequence293

28.Compounds of Medicinal and Biological Interest303

29.Sulfanilamide310

30.3-Phenylsydnone314

31.Reduction Products of Nitrobenzene317

32.Replacement of the Diazonium Group by Halogen323

33.Replacement of the Diazonium Group by Hydrogen327

34.Replacement of the Diazonium Group by Hydroxyl332

35.Dyes and Indicators338

36.The Cannizzaro Reaction348

37.Aldol Condensations354

38.A Modified Wittig Synthesis360

39.The Perkin Reaction364

40.The Meerwein Arylation Reaction370

41.The Benzoin Condensation375

42.The Benzilic Acid Rearrangement384

43.Reduction of Benzophenone by Sodium Borohydride389

44.Triphenylmethanol393

45.Derivatives of 1,1-Diphenylethane399

46.The Pinacol-Pinacolone Rearrangement402

47.Polycyclic Quinones407

48.Enamine Synthesis of a Diketone412

49.Reactions of Ethyl Acetoacetate417

50.The Acetoacetic Ester Synthesis of Ketones421

51.Benzothiazoles427

52.Derivatives of Indole and of Quinoline430

53.Wagner-Meerwein Rearrangements435

54.The Diels-Alder Reaction438

55.The Diels-Alder Diene Synthesis445

56.Ferrocene and Acetylferrocene452

57.Chemical Kinetics458

Identification of Organic Compounds463

58.Identification by Chemical Methods465

59.Identification of Structure by Spectroscopic Methods482

Suggestions for Supplementary Experiments502

Literature of Organic Chemistry505

Appendix519

List of Figures521

List of Tables524

Tables of Physical Data525

Index531