Organic Chemistry/Book outline

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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