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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
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- Vital force theory
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- Synthesis of urea
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- Organic vs inorganic chemistry
- Atomic structure
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- Nucleus and electrons
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- Shells and orbitals
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- Filling electron shells
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- Octet rule and exceptions
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- Molecular orbitals
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- Hybridization
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- Electron wave function
- Ionic bonding
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- Formal charge
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- Ionization energy
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- Electron affinity
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- Electronegativity
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- Dipole moment
- Covalent bonding
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- Molecular orbitals in bonding
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- Nonpolar covalent bonds
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- Polar covalent bonds
- Resonance
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- Drawing resonance structures
- Acids and bases
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- Proton donors and acceptors
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- Electron donors and acceptors
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- Electrophiles and nucleophiles
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- pKa and acidity
Alkanes
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- Methane
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- Methane and carbon chains
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- Ethane
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- Propane thru decane
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- Properties of alkanes
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- Drawing alkanes
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- Branched alkanes
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- Constitutional isomers
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- Stereoisomers
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- Naming alkanes
- Cycloalkanes
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- Newman projections and conformers
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- Two hydrogens for every carbon
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- Cycloalkane properties
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- Naming cycloalkanes
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- Conformations
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
Introduction to 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
Haloalkanes
Alcohols
Alkenes
- Alkene properties
- Naming alkenes
- Cycloalkenes
- The pi bond
- Stability of double bonds
- Alkene reactions
Alkynes
- Alkyne properties
- Naming alkynes
- Cycloalkynes
- The triple carbon-carbon bond
- Alkyne reactions
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
- Benzene
- Other aromatic compounds
Aromatic reactions
- Electrophilic aromatic substitution
- Nucleophilic aromatic substitution
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
