Section A-Structure and bonding 1
A1 Atomic structure of carbon 1
A2 Covalent bonding and hybridization 3
A3 sp3 Hybridization 5
A4 sp2 Hybridization 8
CONTENTSPreface 9
A5 sp Hybridization 14
A6 Bonds and hybridized centers 17
Section B-Alkanes and cycloalkanes 19
B1 Definition 19
B2 Drawing structures 20
B3 Nomenclature 22
C1 Recognition of functional groups 27
Section C-Functional groups 27
C2 Aliphatic and aromatic functional groups 29
C3 Intermolecular bonding 30
C4 Properties and reactions 33
C5 Nomenclature of functional groups 35
C6 Primary，secondary，tertiary，and quaternary nomenclature 43
Section D-Stereochemistry 45
D1 Constitutional isomers 45
D2 Configurational isomers-alkenes and cycloalkanes 46
D3 Configurational isomers-optical isomers 49
D4 Conformational isomers 56
E1 Definition 63
Section E-Nucleophiles and electrophiles 63
E2 Charged species 64
E3 Neutral inorganic species 66
E4 Organic structures 69
Section F-Reactions and mechanisms 73
F1 Reactions 73
F2 Mechanisms 75
Section G-Acid-base reactions 79
G1 Bronsted-Lowry acids and bases 79
G2 Acid strength 82
G3 Base strength 88
G4 Lewis acids and bases 94
G5 Enolates 95
Section H-Alkenes and alkynes 99
H1 Preparation of alkenes and alkynes 99
H2 Properties of alkenes and alkynes 101
H3 Electrophilic addition to symmetrical alkenes 104
H4 Electrophilic addition to unsymmetrical alkenes 111
H5 Carbocation stabilization 114
H6 Reduction and oxidation of alkenes 116
H7 Hydroboration of alkenes 120
H8 Electrophilic additions to alkynes 123
H9 Reduction of alkynes 126
H10 Alkylation of terminal alkynes 128
H11 Conjugated dienes 130
I1 Aromaticity 135
Section I-Aromatic chemistry 135
I2 Preparation and properties of aromatic compounds 137
I3 Electrophilic substitutions of benzene 139
I4 Synthesis of mono-substituted benzenes 147
I5 Electrophilic substitutions of mono-substitutedaromatic rings 150
I6 Synthesis of di-and tri-substituted benzenes 160
I7 Oxidation and reduction 164
Section J-Aldehydes and ketones 167
J1 Preparation 167
J2 Properties 169
J3 Nucleophilic addition 172
J4 Nucleophilic addition-charged nucleophiles 174
J5 Electronic and steric effects 180
J6 Nucleophilic addition-nitrogen nucleophiles 183
J7 Nucleophilic addition-oxygen and sulfur nucleophiles 186
J8 Reactions of enolate ions 190
J9 α-Halogenation 197
J10 Reduction and oxidation 199
J11 α，β-Unsaturated aldehydes and ketones 201
Section K-Carboxylic acids and carboxylic acid derivatives 205
K1 Structure and properties 205
K2 Nucleophilic substitution 208
K3 Reactivity 212
K4 Preparations of carboxylic acids 216
K5 Preparations of carboxylic acid derivatives 218
K6 Reactions 223
K7 Enolate reactions 233
Section L-Alkyl halides 237
L1 Preparation and physical properties 237
L2 Nucleophilic substitution 239
L3 Factors affecting SN2 versus SN1 reactions 244
L4 Elimination 249
L5 Elimination versus substitution 253
L6 Reactions of alkyl halides 255
L7 Organometallic reactions 258
Section M-Alcohols，phenols，and thiols 261
M1 Preparation of alcohols 261
M2 Preparation of phenols 262
M3 Properties of alcohols and phenols 264
M4 Reactions of alcohols 268
M5 Reactions of phenols 275
M6 Chemistry of thiols 279
Section N-Ethers，epoxides，and thioethers 281
N1 Preparation of ethers，epoxides，and thioethers 281
N2 Properties of ethers，epoxides，and thioethers 284
N3 Reactions of ethers，epoxides，and thioethers 286
Section O-Amines and nitriles 291
O1 Preparation of amines 291
O2 Properties of amines 295
O3 Reactions of amines 300
O4 Chemistry of nitriles 306
Further reading 309
Index 311