CONTENTS Preface Section A-Structure and bonding Atomic structure of carbon 1 AI gand hybridization sp 3 sp 公 Section B-Alkanes and cycloalkanes 19 B1 Definition B2 Drawing structures B3 Nomenclature Section C-Functional groups C1 Recognition of functional groups Aliphatic and aromatic functional groups Intermolecular bonding 779035 compounds with functional groups Section D-Stereochemistry D1 Constitutional isomers D2 Configurational isomers-alkenes and cycloalkanes D3 Configurational isomers-optical isomers D4 Conformational isomers Section E-Nucleophiles and electrophiles 63 Definition Charged species Neutral inorganic species Organic structures Section F-Reactions and mechanisms Mechanisms Section G-Acid-base reactions G1 Bronsted-Lowry acids and bases 79 G2 Acid strength G3 Base strength Lewis acids and bases EnolatesPreface ix 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 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 Section C – Functional groups 27 C1 Recognition of functional groups 27 C2 Aliphatic and aromatic functional groups 29 C3 Intermolecular bonding 30 C4 Properties and reactions 33 C5 Nomenclature of compounds with 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 Section E – Nucleophiles and electrophiles 63 E1 Definition 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 Brønsted–Lowry acids and bases 79 G2 Acid strength 82 G3 Base strength 88 G4 Lewis acids and bases 94 G5 Enolates 95 CONTENTS