Reaction Mechanisms in Organic Chemistry

BASIC CONCEPTS
Covalent Bonding and Hybridization
Electrophiles and Nucleophiles
Inductive and Mesomeric Effects
Formal Charge And Oxidation Number
Acids And Bases
Reaction Kinetics And Energy Diagrams

NUCLEOPHILIC SUBSTITUTION REACTIONS
Unimolecular Substitution Reactions SN1
Stereochemistry in SN1 Reactions
Optical Activity
Bimolecular Substitution Reactions SN2
Stereochemistry of SN2 Reactions
Nucleophilic Substitution On Allylic Systems: Allylic Rearrangement
Internal Nucleophilic Substitution Reaction SNi
Neighboring Group Participation in Nucleophilic Substitution Reactions
Ambident Nucleophiles
Various Nucleophilic Substitution Reactions

ELIMINATION REACTIONS
Unimolecular Elimination Reactions, E1
Bimolecular Elimination Reactions, E2
Unimolecular Conjugate Base
Halogene Elimination
Hofmann Elimination: Quaternary Ammonium Salts
Pyrolitic Eliminations: Intramolecular cis-Elimination Reactions
Elimination at the Bridgehead: Bredt?s Rule

ADDITION REACTIONS
Halogen Addition To Double Bonds: Halogenation
Addition of Hydrogen Halides to Double Bonds: Markovnikov?s Rule
Anti-Markovnikov Addition of Hydrogen Halides to Alkenes
Addition of Water to Alkenes
Oxymercuration and Demercuration
Hydroboration of Alkenes: Anti-Markovnikov Hydration
Epoxidation of the Alkenes
Vicinal cis-Dihydroxylation
Dihydroxylation via PIFA
Enzymatic Dihydroxylation
Ozonolysis: Oxidative Cleavage of Alkenes
Reduction of Alkenes
Addition to Conjugated Dienes

CARBONYL COMPOUNDS AND THEIR REACTIONS
Structure-Reactivity Relationships
Reactions of Carbonyl Compounds
Carbonyl Addition Reactions
Umpolung: Polarity Inversion of Aldehyde Carbonyl Group
Reactions of Aldehydes and Ketones with Amines
Reduction of Carbonyl Groups
Reaction of Carbonyl Groups with Organometallic Compounds
Reaction of Carbonyl Groups with Ylides
Phosphonium Ylides and Wittig Reaction
Reactivity of alpha-Carbon Atom
Keto-Enol Tautomerism
Proton-Deuterium Exchange
alpha-Halogenation of Ketones and Aldehydes: Haloform Reaction
Hell-Volhard-Zelinsky Reaction
alpha-Alkylation of Carbonyl Compounds
Enolates Derived from 1,3-Dicarbonyl Compounds
Condensation Reactions of Carbonyl Compounds
Typical Reactions of Acids and Esters
Transesterification

AROMATIC COMPOUNDS
Structure of Benzene
Aromatic, Antiaromatic, and Nonaromatic Compounds
Determination of the Molecular orbitals of Aromatic Compounds
What are the criteria for aromaticity? How does one quantify aromaticity?
Homoaromaticity
Möbius Aromaticity
Aromatic Ions
Annulenes
Aromaticity in Fused Systems
Aromaticity in Heterocyclic Compounds
Electrophilic Aromatic Substitution: Chemistry of Benzene
Reactivity of Monosubstituted Benzene Derivatives
Directing Effects of Substituents: Activating Groups
Electrophilic Aromatic Substitution on Disubstituted Benzenes
Functionalization of the Side Chain Substituents of Benzene
Nucleophilic Aromatic Substitution Reactions
Polycyclic Aromatic Compounds
Benzenoid Aromatic Compounds

REACTIVE INTERMEDIATES
Carbocations
Carbanions
Carbenes
Nitrenes
Radicals
Singlet Oxygen

PERICYCLIC REACTIONS
Woodward Hoffmann Rules
Frontier Orbitals
Electrocyclic Reactions
Application of Woodward Hoffmann Rules
Correlation Diagrams
Cycloaddition Reactions
Secondary Orbital Interaction
Orbital Coefficients
Sigmatropic Reactions
Cope and Claisen Rearrangement

CARBON-CARBON (C-C) COUPLING REACTIONS
History
Mizoroki-Heck Coupling Reaction
Stille-Coupling Reaction
Suzuki-Miyaura Coupling Reaction
Negishi-Coupling Reaction
Sonogashira-Coupling Reaction
Kumada-Coupling Reaction
Hiyama-Coupling Reaction
Hiyama-Denmark Coupling
Buchwald-Hartwig Coupling
Tsuji-Trost Coupling
Palladium-catalyzed Carbonylation Reactions
Carbonylative Coupling Reactions with Organometallic Reagents
Mo(CO)6-Mediated Carbonylation