THE THEORY OF ORGANIC CHEMISTRY AN ADVANCED COURSE2025|PDF|Epub|mobi|kindle电子书版本百度云盘下载

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Ⅰ．THE DEVELOPMENT OF STRUCTURAL CHEMISTRY1

1．Valence1

2．Structural Isomerism6

3．The Persistence of Structure6

4．Structural Analogy10

5．Structural Iteration12

6．Tautomerism14

7．Stereoisomerism16

8．The Constancy of Valence20

Ⅱ．ATOMIC STRUCTURE26

9．The Nuclear Atom26

10．The Lewis Atom27

11．The Quantum Theory of the Atom28

11a．The Bohr atom28

11b．The wave mechanical atom29

Ⅲ．MOLECULAR STRUCTURE38

12．Electronic Structural Formulas38

12a．Co-ordination number42

12b．Charge distribution43

12c．Acids,bases,and free radicals45

13．The Electron Pair Bond in Quantum Mechanics46

13a．Methods of approximation47

13b．The hydrogen molecule51

13c．The one-electron bond58

13d．Bond dipole59

13e．The tetrahedral carbon atom60

Ⅳ．GROUP INTERACTION62

14．Group Interactions without Considering Resonance62

14a．Steric hindrance62

14b．Negativity63

14c．Polarity and induction63

14d．The Hixon-Johns method65

15．Conjugation67

Ⅳ．GROUP INTERACTION(Cont．)70

16．Resonance and Mesomerism70

16a．Mesomerism as a tautomerism70

16b．Molecular resonance as an extension of the Lewis theory73

16c．Molecular resonance as a theorem in quantum mechanics81

Ⅴ．PHYSICAL PROPERTIES91

17．Bond Distances and Angles92

17a．Experimental methods92

17b．Bond distances111

17c．The hydrogen bond116

17d．Bond angles121

17e．Free rotation124

18．Dipole Moments126

18a．Bond moments129

18b．Sign of dipole moment132

18c．Vector addition of dipole moments133

18d．Dipole moment and rotation about a single bond139

18e．Dipole moment and resonance144

19．Raman Spectra and Force Constants151

19a．Force constants153

20．Color155

20a．Older theories157

20b．Quantum mechanical calculations157

20c．Complexity of spectra159

20d．Electrons as quantized oscillators162

20e．Approximately linear oscillators163

20f．Conjugation,insulation,partials168

20g．The function of auxochromes172

20h．Oscillators in more than one direction174

20i．Acid-base indicators179

Ⅵ．EQUILIBRIUM—ACID STRENGTH183

21．Equilibrium183

22．Acids and Bases186

23．Acid Strength and Structure188

23a．Mechanism of comparison of acid strength188

23b．Mechanism for the description of intramolecular action;division into contributing factors192

24．Acids without Resonance201

24a．Discussion of special cases205

24b．The electrostatic method216

25．The Fatty Acids217

26．Unsaturated Acids233

26s．Cross-conjugation235

27．The Aromatic Acids240

27a．Resonance of aromatic nuclei240

27b．Classification of aromatic acids242

27c．Meta groups245

27d．Para groups249

27e．Ortho groups257

28．Miscellaneous Acids265

28a．Ammonia acids266

28b．Methane acids268

28c．Generalized acids269

Ⅶ．ENERGY RELATIONSHIPS IN SOME OTHER REACTIONS271

29．Ionic Resonance and the Heat of Formation271

30．Valence Bond Resonance and Heat of Formation272

30a．The branched-chain effect274

30b．Ring strain278

30c．Resonance energies280

31．Tautomerism281

31a．Keto-enol equilibria289

31b．Solvent effect296

31c．Other tautomeric systems297

32．Oxidation-Reduction Potentials303

32a．Homopolar valence bond resonance305

32b．Ionic resonance and induction315

33．Free Radicals317

33a．Trivalent carbon319

33b．Divalent nitrogen and tetravalent nitrogen326

33c．Monovalent oxygen332

33d．Diradicals333

34．cis-trans Isomerism of Olefins339

35．Equilibrium in the Addition to the Double Bond343

Ⅷ．THE RATE FACTOR IN CHEMICAL BEHAVIOR352

36．The Variation of Rate with Concentration353

36a．Reversible reactions354

36b．Simultaneous reaction356

36c．Successive reactions357

36d．Catalysis362

36e．Chain reactions364

36f．Inhibitors365

37．The Temperature Coefficient of Reaction Rate367

37a．Unimolecular reactions369

37b．Bimolecular reactions372

37c．The temperature coefficient of a complex reaction375

38．Transition state376

39．Molecular association384

40．The Quantum Mechanical Treatment387

40a．The Eyring-Polanyi method390

Ⅸ．THE REACTIONS OF ACIDS AND BASES WITH NEUTRAL SUB-STANCES—THREE-CENTER REACTIONS393

41．The Mechanisms of the Reactions394

41a．The Walden inversion395

41b．The differentiation of rate-determining and preliminary reversible reactions396

41c．The salt effect397

41d．Reaction with both hydrogen ion and undissociated acid399

41e．Reaction of substrate with either acid or base401

41f．Lowry＇s mechanism403

41g．Unimolecular and bimolecular hydrolysis405

41h．Slow and fast reactions407

42．The Strength of the Reacting Acid or Base(C)408

42a．Br？nsted＇s equation409

42b．Hammett＇s equation416

42c．The relationship between Br？nsted＇s and Hammett＇s equations420

42d．Acids without hydrogen atoms420

42e．Charged and neutral bases421

42f．The polarizability effect422

43．The Strength of the Product Acid or Base(A)423

44．The Middle Group(B)in the Three-Center Reaction426

45．Inductive and Tautomeric Effects428

46．The Effect of Branching Chains430

47．The Effect of Resonance on Reaction Rate434

47a．Effect of resonance in a reacting or product base435

47b．Resonance of the middle group of the transition state436

47c．Resonance effects of para substituents440

48．Steric Effects443

Ⅹ．REACTIONS OF THE DOUBLE BOND449

49．The Ethylenic Double Bond451

49a．Ethylenes as bases or pseudo-bases451

49b．Stereochemistry of addition reactions454

49c．Macropolymerization455

50．The Carbonyl Double Bond457

50a．Addition of bisulfite ion458

50b．Oximes,hydrazones,and semicarbazones459

50c．Addition of organometallic compounds462

50d．The aldol condensation463

50e．The Cannizzaro reaction466

51．Conjugate Systems467

52．Substitution Reactions of Benzene470

52a．The directing influence of substituents471

52b．Application of Hammett＇s equation to para and meta substitution480

52c．The reaction of benzene as a pseudo-acid481

52d．The reaction of carbonyl compounds with phenols and anilines482

52e．The relationship between addition to ethylene and substitution in benzene483

52f．Condensed-ring systems484

53．Four-Center Reactions487

53a．Aromatic rings in the diene condensation490

AUTHOR INDEX493

SUBJECT INDEX499