Efficiently Studying Organic Chemistry

Contents 1

Preface 6

Organic Chemistry 7

1 Atomic Orbitals, Electronic Configurations 8

2 Covalent Bonding 10

3 Hybridization of Atomic Orbitals 12

4 Covalent Carbon-Carbon Bonding 14

5 Alkanes 16

6 Skeletal Structure, Structural Isomerism 18

7 Basic Rules of Nomenclature 20

8 Drawing Molecular Structures 22

9 Conformation 24

10 Reactive Intermediates 26

11 Basic Types of Organic Reactions 28

12 Energy Turnover of Chemical Reactions 30

13 Radical Substitution 32

14 Alkenes, Skeletal and Configurational Isomers 34

15 Synthesis of Alkenes 36

16 Additions to Alkenes 40

17 Dienes 44

18 Additions and Cycloadditions with 1,3-Dienes 46

19 Alkynes 48

20 Cycloalkanes 52

21 Basic Syntheses of Cycloalkanes and Cycloalkenes 56

22 Reactions of Cycloalkanes and Cycloalkenes 58

23 Benzene, Aromaticity, Aromatic Compounds 60

24 Benzenoid Aromatic Compounds 62

25 Electrophilic Substitution of Benzene 64

26 Electrophilic Second Substitution of Benzenes 66

27 Other Reactions of Benzenoid Aromatics 68

28 Polycyclic Benzenoid Aromatic Compounds 70

29 Non-benzenoid Aromatic Compounds 74

30 Alkyl Halides 76

31 Mechanisms of Nucleophilic Substitution 80

32 Organometal Compounds 82

33 Alcohols 84

34 Diols, Triols 88

35 Reactions of Alcohols 90

36 Dehydration of Alcohols 92

37 Ethers 94

38 Amines 96

39 Reactions of Amines 98

40 Diazo and Azo Compounds 102

41 Carboxylic Acids 106

42 Carboxylic Acid Derivatives 110

43 Substituted Carboxylic Acids 114

44 Absolute Configuration 118

45 Enantiomers without Carbon as Stereogenic Center 122

46 Diastereomers 124

47 Aldehydes 126

48 Ketones 130

49 Carbonyl Reactions 132

50 CH Acidity of Carbonyl Compounds 136

51 1,3-Dicarbonyl Compounds 138

52 Phenols 142

53 Quinones 146

54 Organosulfur Compounds 150

55 Carbonic Acid Derivatives 154

56 Heterocumulenes 158

57 Rearrangements 160

58 Polymers, Polymerization 164

59 Syntheses with Organosilicon Compounds 168

60 Heteroalicycles 170

61 Five-Membered Aromatic Heterocycles 174

62 Six-Membered Aromatic Heterocycles 178

63 Benzo-Fused Five-Membered Heteroaromatics 182

64 Benzo-Fused Six-Membered Heteroaromatics 186

65 Fused Aromatic Heterocycles 190

66 Absorption of Light, Color, Dyes 194

67 Porphyrinoids 198

68 Amino Acids 200

69 Peptides, Proteins 202

70 Alkaloids 206

71 Carbohydrates: Aldoses and Ketoses 208

72 Carbohydrates: Oligo- and Polysaccharides 212

73 Nucleic Acids: DNA and RNA 214

74 Lipids 216

75 Polyketides 218

76 Terpenes 220

77 Steroids 224

78 Selectivity and Specificity of Organic Reactions 226

79 Prochirality, Enantioselectivity 230

80 Planning Organic Syntheses 232

81 Aspects of Molecular Structure 236

82 Mass Spectrometry 238

83 Infrared Spectroscopy 240

84 Nuclear Magnetic Resonance: Proton NMR 242

85 Nuclear Magnetic Resonance: Carbon-13 NMR 246

86 Nuclear Magnetic Resonance: Two-Dimensional NMR 248

Working on Questions 250

Subject Index 295

Periodic Table of the Elements 314

Selected Reference Sources 316