Organometallic Chemistry

Outline for Organometallic Chemistry TEST flastname

1. Introduction to Organometallic Chemistry

  • 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.

  • 1.2 Historical Background
    • Brief history of key discoveries in organometallic chemistry (e.g., Grignard reagents, ferrocene).


2. The 18-Electron Rule

  • 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).


4. Organometallic Reactions

  • 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).


5. Applications of Organometallic Chemistry

  • 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).


6. References and Further Reading

  • Key textbooks and review articles on organometallic chemistry.

  • Online resources and databases for further exploration.


Notes for Students

  • 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.