# 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