Organic Chemistry/Book outline

Authors' To-Do Lists Organic chemistry > Organic textbook expanded contents Foreword Purpose and mission Content and contributions Foundational concepts of organic chemistry History of organic chemistry Vital force theory Synthesis of urea Organic vs inorganic chemistry Atomic structure Nucleus and electrons Shells and orbitals Filling electron shells Octet rule and exceptions Molecular orbitals Hybridization Electron wave function Ionic bonding Formal charge Ionization energy Electron affinity Electronegativity Dipole moment Covalent bonding Molecular orbitals in bonding Nonpolar covalent bonds Polar covalent bonds Resonance Drawing resonance structures Acids and bases Proton donors and acceptors Electron donors and acceptors Electrophiles and nucleophiles pKa and acidity Alkanes Methane Ethane Propane thru decane Stereoisomers Cycloalkanes Two hydrogens for every carbon Cycloalkane properties Naming cycloalkanes Introduction to reactions Overview of addition, elimination, substitution and rearrangement reactions Polar and radical reactions Redox reactions Functional groups in reactions Drawing reactions Rates and equilibria Gibbs free energy Bond dissociation energies Energy diagrams Transition states Carbocations Addition reactions Rearrangement reactions Overview of Functional Groups Introduction to alcohols Introduction to phenols Introduction to ethers Introduction to epoxides Introduction to aldehydes Introduction to ketones Introduction to carboxylic acid Introduction to carboxylic acid derivatives Alkenes Alkene properties Cycloalkenes The pi bond Stability of double bonds Alkene reactions Alkynes Haloalkanes Alcohols Chirality Handedness Enantiomers Stereogenic centers Optical activity Absolute and relative configurations Diastereomers Meso compounds R-S notational system Multiple chiral centers Chirality beyond carbon Dienes Three kinds of dienes Conjugation Diene properties and reactions Cyclodienes Aromaticity Other aromatic compounds Aromatic reactions Spectroscopy Historic analytical techniques Spectrometry Spectroscopy proper Organometallics Chemistry of various functional groups Organic chemistry and biochemistry Amino acids Proteins Carbohydrates Lipids Periodic table Valence Bonding: Electronegativity Hybridization Lewis structures Resonance Formal charges Conjugation Aromaticity Nomenclature Alkanes Cycloalkanes Alkenes Alkynes Haloalkanes Alcohols Isomers Structural isomers Stereoisomers Enantiomers, R, S Racemates Conformational cis-trans E, Z Structure and properties Alkanes Alkenes Alkynes Alcohols Haloalkanes Arenes Reactions Alkanes (and cycloalkanes) (Combustion) Free radical halogenation Alkenes Hydrogenation Hydration -> oxymercuration/demercuration Halogenation Hydrohalogenation Hydroboration/oxidation Halohydrins Oxydation (Ozonolysis, osmylation, epoxidation/peroxidation) Allylic bromination Alkynes Hydrogenation Hydration Halogenation Hydrohalogenation Ozonolysis Alkylation Alcohols, haloalkanes Nucleophilic substitution (SN1, SN2) Elimination (E1, E2) Carbocation rearrangements Conjugated (1,3-) dienes Direct (1,2-) and conjugate (1,4-) addition Kinetic and thermodynamic control Diels-Alder reaction Aromatic compounds Hydrogenation Ozonolysis Benzylic bromination Benzylic oxydation Vinylic benzenes (styrenes) Chirality Cahn-Ingold-Prelog nomenclature of chiral atoms