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