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Section A-Structure and bonding1

A1 Atomic structure of carbon1

A2 Covalent bonding and hybridization3

A3 sp3 Hybridization5

A4 sp2 Hybridization8

CONTENTSPreface9

A5 sp Hybridization14

A6 Bonds and hybridized centers17

Section B-Alkanes and cycloalkanes19

B1 Definition19

B2 Drawing structures20

B3 Nomenclature22

C1 Recognition of functional groups27

Section C-Functional groups27

C2 Aliphatic and aromatic functional groups29

C3 Intermolecular bonding30

C4 Properties and reactions33

C5 Nomenclature of functional groups35

C6 Primary，secondary，tertiary，and quaternary nomenclature43

Section D-Stereochemistry45

D1 Constitutional isomers45

D2 Configurational isomers-alkenes and cycloalkanes46

D3 Configurational isomers-optical isomers49

D4 Conformational isomers56

E1 Definition63

Section E-Nucleophiles and electrophiles63

E2 Charged species64

E3 Neutral inorganic species66

E4 Organic structures69

Section F-Reactions and mechanisms73

F1 Reactions73

F2 Mechanisms75

Section G-Acid-base reactions79

G1 Bronsted-Lowry acids and bases79

G2 Acid strength82

G3 Base strength88

G4 Lewis acids and bases94

G5 Enolates95

Section H-Alkenes and alkynes99

H1 Preparation of alkenes and alkynes99

H2 Properties of alkenes and alkynes101

H3 Electrophilic addition to symmetrical alkenes104

H4 Electrophilic addition to unsymmetrical alkenes111

H5 Carbocation stabilization114

H6 Reduction and oxidation of alkenes116

H7 Hydroboration of alkenes120

H8 Electrophilic additions to alkynes123

H9 Reduction of alkynes126

H10 Alkylation of terminal alkynes128

H11 Conjugated dienes130

I1 Aromaticity135

Section I-Aromatic chemistry135

I2 Preparation and properties of aromatic compounds137

I3 Electrophilic substitutions of benzene139

I4 Synthesis of mono-substituted benzenes147

I5 Electrophilic substitutions of mono-substitutedaromatic rings150

I6 Synthesis of di-and tri-substituted benzenes160

I7 Oxidation and reduction164

Section J-Aldehydes and ketones167

J1 Preparation167

J2 Properties169

J3 Nucleophilic addition172

J4 Nucleophilic addition-charged nucleophiles174

J5 Electronic and steric effects180

J6 Nucleophilic addition-nitrogen nucleophiles183

J7 Nucleophilic addition-oxygen and sulfur nucleophiles186

J8 Reactions of enolate ions190

J9 α-Halogenation197

J10 Reduction and oxidation199

J11 α，β-Unsaturated aldehydes and ketones201

Section K-Carboxylic acids and carboxylic acid derivatives205

K1 Structure and properties205

K2 Nucleophilic substitution208

K3 Reactivity212

K4 Preparations of carboxylic acids216

K5 Preparations of carboxylic acid derivatives218

K6 Reactions223

K7 Enolate reactions233

Section L-Alkyl halides237

L1 Preparation and physical properties237

L2 Nucleophilic substitution239

L3 Factors affecting SN2 versus SN1 reactions244

L4 Elimination249

L5 Elimination versus substitution253

L6 Reactions of alkyl halides255

L7 Organometallic reactions258

Section M-Alcohols，phenols，and thiols261

M1 Preparation of alcohols261

M2 Preparation of phenols262

M3 Properties of alcohols and phenols264

M4 Reactions of alcohols268

M5 Reactions of phenols275

M6 Chemistry of thiols279

Section N-Ethers，epoxides，and thioethers281

N1 Preparation of ethers，epoxides，and thioethers281

N2 Properties of ethers，epoxides，and thioethers284

N3 Reactions of ethers，epoxides，and thioethers286

Section O-Amines and nitriles291

O1 Preparation of amines291

O2 Properties of amines295

O3 Reactions of amines300

O4 Chemistry of nitriles306

Further reading309

Index311