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Organic Chemistry: Volume I
CONTENTS
VOLUME I 1-457
CHAPTER 1 THE CHEMICAL BOND hal. 1
1.1 paramters of molecular structure hal. 2
1.2 localized covalent bond hal. 5
1.3 delocalized chemical bond: the concept of resonance hal. 28
1.4 other types of bonding hal. 38
CHAPTER 2 STEREOISOMERISM hal. 52
2.1 geometric isomerism hal. 53
2.2 conformational isomerism hal. 63
2.3 optical isomerism hal. 72
CHAPTER 3 MODERN METHODS OF THE DETERMINATION OF STRUCTURE: ORGANIC SPECTROSCOPY hal. 98
3.1 the electromagnetic spectrum
3.2 electronic spectra
3.3 infrared spectroscopy
3.4 nuclear magnetic resonance spectroscopy
3.5 mass spectrometry hal. 128
CHAPTER 4 GENERAL PRINCIPLES OF ORGANIC RAECTION MECHANISMS hal. 140
4.1 types of reagents hal. 141
4.2 types of organic reactions hal. 143
4.3 energy considerations hal. 145
4.4 reactive intermediates hal. 153
4.5 methods of determination of reaction mechanisms hal. 169
CHAPTER 5 ALIPHATIC HYDROCARBONS I: ALKANES AND CYCLOALKANES hal. 180
5.1 alkanes hal. 181
5.2 cycloalkanes hal. 190
CHAPTER 6 ALIPHATIC HYDROCARBONS II: ALKENES, CYCLOALKENES, DIENES AND ALKYNES hal. 216
6.1 alkenes hal. 216
6.2 cycloalkenes hal. 252
6.3 dienes hal. 256
6.4 alkynes hal. 273
CHAPTER 7 AROMATIC HYDROCARBONS I: BENZENE AND AROMATICITY hal. 291
7.1 industrial source hal. 292
7.2 nomenclature of benzene derivatives hal. 293
7.3 the aryl group hal. 296
7.4 aromatic nucleus and side chain hal. 296
7.5 structure of benzene: molecular formula and kekule structure hal. 296
7.6 aromaticity: the huckel rule hal. 302
7.7 method sof formation of benzene hal. 308
7.8 physical properties of benzene hal. 309
7.9 chemical reactions of benzene hal. 309
CHAPTER 8 AROMATIC ELECTROPHILIC SUBTITUTION hal. 318
8.1 general pattern of the mechanism hal. 318
8.2 role of a-and n-complexes in aromatic electrophilic subtitution hal. 320
8.3 electrophilic subtitution reactions of benzene hak, 323
8.4 effect of subtituents hal. 329
8.5 the orthi-para ratio hal. 334
8.6 further subtituent in disubtituted benzenes: competition between subtituents hal. 336
CHAPTER 9 AROMATIC HYDROCARBON II: ARENES hal. 342
9.1 nomenclature hal. 342
9.2 alkybenzenes hal. 345
9.3 alkenylbenzenes hal. 360
9.4 alkynylbenzenes hal. 366
9.5 biphenyl hal. 367
9.6 diphenylmethane hal. 371
9.7 triphenylmethane (tritane) hal. 373
CHAPTER 10 HALOGEN COMPOUNDS hal. 378
1o.1 alkyl halides hal. 379
10.2 alkenyl halides hal. 401
10.3 polyhalogen compounds hal. 401
10.4 aryl halides hal. 405
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