1.1 Definition and Scope
Definition of organometallic compounds (compounds with metal-carbon bonds).
Importance of organometallic chemistry in catalysis, industrial processes, and organic synthesis.
Brief history of key discoveries in organometallic chemistry (e.g., Grignard reagents, ferrocene).
2.1 Overview
Explanation of the 18-electron rule and its significance in transition metal complexes.
Comparison to the octet rule in main-group chemistry.
2.2 Electron Counting
Step-by-step guide to counting electrons in organometallic complexes.
Examples of 18-electron complexes (e.g., Fe(CO)₅, Cr(CO)₆).
2.3 Exceptions to the 18-Electron Rule
Discussion of 16-electron complexes and their stability (e.g., square planar Pt(II) complexes).
Factors influencing deviations from the 18-electron rule (e.g., steric effects, electronic effects).
3. Common Organometallic Ligands
Overview of common ligands (e.g., CO, phosphines, cyclopentadienyl, hydrides, alkyls).
Bonding modes (e.g., η¹, η², η⁵, π-bonding).
3.1 Ligand Substitution
3.1.1 Overview
Definition and importance of ligand substitution reactions.
3.1.2 Mechanisms
Associative (A), dissociative (D), and interchange (I) mechanisms.
Examples of ligand substitution reactions (e.g., substitution of CO in metal carbonyls).
3.2 Oxidative Addition
3.2.1 Overview
Definition and significance of oxidative addition in catalysis.
3.2.2 Mechanisms
Concerted, SN₂, and radical mechanisms.
Examples (e.g., addition of H₂ or alkyl halides to metal centers).
3.3 Reductive Elimination
3.3.1 Overview
Definition and role in forming C-C or C-X bonds.
3.3.2 Mechanisms
Concerted reductive elimination.
Examples (e.g., formation of ethane from a Pt(IV) complex).
3.4 Migratory Insertion
3.4.1 Overview
Definition and importance in polymerization and carbonylation reactions.
3.4.2 Mechanisms
1,1-insertion and 1,2-insertion.
Examples (e.g., CO insertion into metal-alkyl bonds).
3.5 β-Hydride Elimination
3.5.1 Overview
Definition and role in forming alkenes from metal-alkyl complexes.
3.5.2 Mechanisms
Requirements for β-hydride elimination (e.g., vacant coordination site, β-hydrogen).
Examples (e.g., formation of ethylene from a metal-ethyl complex).
3.6 Nucleophilic Addition to Coordinated Ligands
3.6.1 Overview
Definition and examples of nucleophilic attack on coordinated ligands (e.g., CO, alkenes).
3.6.2 Mechanisms
Attack on π-acceptor ligands.
Examples (e.g., formation of aldehydes via CO insertion and nucleophilic attack).
4.1 Catalysis
Role of organometallic complexes in homogeneous catalysis (e.g., hydrogenation, hydroformylation, polymerization).
4.2 Industrial Processes
Examples of industrial applications (e.g., Monsanto acetic acid process, Ziegler-Natta polymerization).
4.3 Organic Synthesis
Use of organometallic reagents in organic synthesis (e.g., Grignard reagents, Suzuki coupling).
Key textbooks and review articles on organometallic chemistry.
Online resources and databases for further exploration.
Use clear, concise language and include diagrams to illustrate key concepts (e.g., reaction mechanisms, orbital interactions).
Provide specific examples for each reaction type and mechanism.
Highlight the practical applications of organometallic chemistry in catalysis and synthesis.