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CHM676 Organometallic Chemistry UITM Assignment Answer, Malaysia

CHM676 Organometallic Chemistry is an advanced course designed to provide Malaysian students with a deep understanding of compounds containing metal-carbon bonds and their significant role in the field of chemistry. This course explores the fundamental principles of organometallic chemistry, focusing on the bonding between organic groups and metals through the interaction of lone pairs of electrons and π-electrons, particularly in olefin complexes. As a Malaysian student, you will have the opportunity to delve into this exciting field, gaining insights into the chemistry of metal-carbon compounds and their applications.

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Assignment Task 1: Describe the chemistry and bonding of carbonyl and olefin complexes, the chemical properties of metal alkyls, metal aryls as well as carbene and carbyne complexes

Organometallic compounds are an exciting class of compounds in which metal atoms are bonded to organic molecules. They exhibit diverse chemistry, including various bonding modes and reactivity patterns. Here, we will discuss the chemistry and bonding of carbonyl and olefin complexes, the chemical properties of metal alkyls and aryls, as well as carbene and carbyne complexes.

  1. Carbonyl Complexes:
  • Carbonyl complexes involve the bonding of carbon monoxide (CO) to metal atoms. The CO ligand forms a strong sigma (σ) bond with the metal, resulting in a stable structure.
  • Metal carbonyl complexes often exhibit pi (π) backbonding, where electron density is transferred from the metal to the CO ligand, strengthening the metal-ligand interaction.
  • Common examples include nickel tetracarbonyl (Ni(CO)₄) and iron pentacarbonyl (Fe(CO)₅).
  1. Olefin Complexes:
  • Olefin complexes involve the bonding of organic molecules with carbon-carbon double bonds (olefins or alkenes) to metal atoms.
  • The pi bonds in olefins can coordinate to the metal, forming pi bonds with metal d orbitals, while sigma bonds are retained between carbon atoms.
  • Transition metals like platinum are known for forming stable olefin complexes, e.g., bis(ethylene)platinum(0).
  1. Metal Alkyls:
  • Metal alkyls are compounds in which metal atoms are bonded to alkyl groups (R-groups consisting of carbon and hydrogen atoms).
  • They are essential in catalytic processes, especially in the Ziegler-Natta polymerization for producing polyethylene.
  • A well-known example is trimethylaluminum, (CH₃)₃Al, used in the synthesis of various organic compounds.
  1. Metal Aryls:
  • Metal aryl complexes involve the bonding of metal atoms to aromatic ring structures, like benzene rings.
  • These complexes are common in organometallic catalysis, especially in cross-coupling reactions.
  • An example includes palladium(II) acetate, which is used in the Heck reaction for carbon-carbon bond formation.
  1. Carbene and Carbyne Complexes:
  • Carbene complexes feature a divalent carbon atom with two lone pairs of electrons, giving rise to a carbene center (C:).
  • Carbyne complexes involve a trivalent carbon atom with a single unpaired electron and one lone pair.
  • These ligands can form strong sigma bonds with metals and are critical in various reactions, including nucleophilic insertion and catalysis.

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Assignment Task 2: Predict the stability of an organometallic compound through application of the EAN rule

The Effective Atomic Number (EAN) rule is a guideline used to predict the stability and coordination number of organometallic compounds. It is based on the concept that the total number of electrons in the valence shell of a metal center and those contributed by the ligands should ideally equal the atomic number of the noble gas closest to the metal in the periodic table. This is to achieve a stable, closed-shell electron configuration.

Here are the steps to predict the stability of an organometallic compound using the EAN rule:

Step 1: Identify the Metal Center

Determine the metal at the core of your organometallic compound. For the purpose of this example, let’s consider ferrocene, where the metal center is iron (Fe).

Step 2: Determine the Valence Electrons of the Metal

Find the atomic number of the metal in the periodic table to determine the number of valence electrons it has. Iron (Fe) has an atomic number of 26, and its electron configuration is [Ar] 4s² 3d⁶. This means it has a total of 8 valence electrons (4s² + 3d⁶ = 8).

Step 3: Identify the Ligands

Next, identify the ligands attached to the metal center. In ferrocene, the ligands are cyclopentadienyl anions (C₅H₅⁻). Each cyclopentadienyl anion contributes 5 electrons to the metal center.

Step 4: Calculate the EAN

Now, calculate the Effective Atomic Number (EAN) by summing the valence electrons of the metal and those contributed by the ligands:

EAN = Valence Electrons of the Metal + (Number of Ligands x Electrons Contributed by Each Ligand)

EAN = 8 (valence electrons of Fe) + (5 x 2 ligands)

EAN = 8 + 10

EAN = 18

Step 5: Compare EAN with the Nearest Noble Gas

The EAN of 18 corresponds to the noble gas argon (Ar), which has 18 electrons in its closed-shell electron configuration.

Step 6: Analyze the Stability

According to the EAN rule, if the EAN of the organometallic compound matches the electron count of the nearest noble gas (in this case, Ar with 18 electrons), the compound is considered stable. This means that the complexation of iron with the cyclopentadienyl ligands in ferrocene is in accordance with the EAN rule and is expected to be a stable compound.

In this example, the EAN rule was applied to predict the stability of the organometallic compound ferrocene. The EAN of 18 matches the electron count of the nearest noble gas, argon, indicating that the compound is expected to be stable based on the EAN rule. This rule provides valuable insights into the stability and reactivity of various organometallic compounds and helps in understanding their chemical properties.

Assignment Task 3: Characterize organometallic compounds and distinguish their isomers by using infrared and 13C NMR spectroscopy

In organometallic chemistry, the structural characterization of organometallic compounds and the distinction between isomers are essential for understanding their properties and reactivity. Infrared (IR) and 13C Nuclear Magnetic Resonance (NMR) spectroscopy are powerful tools for achieving this. Here’s how these techniques can be applied:

Step 1: Sample Preparation

Start by preparing samples of your organometallic compounds and their isomers. Ensure the samples are pure and well-dissolved in a suitable solvent. The choice of solvent depends on the compound’s solubility and the spectroscopy technique used.

Step 2: Infrared (IR) Spectroscopy

Objective: To identify functional groups and bonding characteristics.

Procedure:

  • Load a sample of the organometallic compound into an IR spectrometer.
  • Record the IR spectrum, which provides information about the stretching and bending vibrations of chemical bonds in the compound.
  • Focus on the regions of the spectrum that are relevant to organometallic compounds, such as metal-carbon (M-C) stretches.
  • Compare the IR spectra of different isomers to identify distinctive peaks or differences in peak intensities.
  • Note the presence or absence of functional groups and the nature of bonding (e.g., η² or η³-coordination).

Interpretation:

  • Peaks in the IR spectrum can help identify functional groups, ligands, and the nature of metal-carbon bonds.
  • The position of M-C stretching frequencies can provide information about the strength of the metal-carbon bond.

Step 3: 13C Nuclear Magnetic Resonance (NMR) Spectroscopy

Objective: To determine the carbon environments and coordination modes of carbon atoms.

Procedure:

  • Load a sample of the organometallic compound into a 13C NMR spectrometer.
  • Record the 13C NMR spectrum, which provides information about the carbon environments and coordination modes.
  • Focus on the regions of the spectrum corresponding to carbon atoms in the organometallic compound.
  • Compare the 13C NMR spectra of different isomers to identify differences in chemical shifts and peak patterns.
  • Observe the number of peaks and their relative intensities, which reveal the different carbon environments in the molecule.

Interpretation:

  • Chemical shifts in the 13C NMR spectra indicate the types of carbon environments (e.g., sp2 carbon, sp3 carbon, or carbon bound to the metal).
  • The number of peaks and their splitting patterns provide information about the coordination modes and symmetry of carbon atoms.

By combining the information obtained from IR and 13C NMR spectroscopy, you can characterize organometallic compounds and distinguish between their isomers. IR spectroscopy helps identify functional groups, bonding characteristics, and the nature of metal-carbon bonds, while 13C NMR spectroscopy provides insights into the carbon environments and coordination modes. This comprehensive analysis allows for a thorough understanding of the structure and properties of these compounds, aiding in further research and applications in organometallic chemistry.

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Assignment Task 4: Apply the knowledge gained on reactions of organometallic compounds in their involvement as catalysts in industry

Organometallic compounds play a crucial role as catalysts in various industrial processes. Their unique reactivity and versatility have made them essential for enhancing the efficiency and selectivity of chemical reactions. Here, we will explore how the knowledge of organometallic compound reactions is applied in industry:

  1. Hydroformylation Reactions:

Organometallic catalysts, particularly those containing rhodium (Rh) or cobalt (Co), are used in the hydroformylation of olefins. This reaction converts alkenes into aldehydes or alcohols and is vital for the production of plasticizers, detergents, and synthetic alcohols. Organometallic complexes facilitate the insertion of carbon monoxide and hydrogen into the alkene’s carbon-carbon double bond.

  1. Polymerization Reactions:

Transition metal catalysts, such as metallocene catalysts, are employed in the polymerization of olefins to produce various plastics. Ziegler-Natta catalysts based on titanium compounds are widely used for the production of polyethylene and polypropylene. Understanding the reactivity and selectivity of organometallic catalysts is critical for optimizing polymerization processes in the plastics industry.

  1. Hydrogenation Reactions:

Transition metal catalysts like palladium (Pd) or platinum (Pt) complexes are crucial in catalytic hydrogenation processes used in the food industry, petrochemical industry, and pharmaceuticals. These catalysts selectively reduce unsaturated compounds (e.g., vegetable oils or drug intermediates) to their saturated counterparts. Knowledge of ligand design and reaction conditions is essential for controlling the hydrogenation process and achieving high yields and product purity.

  1. Cross-Coupling Reactions:

Cross-coupling reactions, such as the Suzuki, Heck, and Negishi reactions, are employed in the synthesis of pharmaceuticals, agrochemicals, and materials. Palladium-based catalysts, often in the form of Pd(0) complexes with phosphine ligands, enable the coupling of organic halides with organoboron, organotin, or organosilicon compounds. Understanding the mechanisms and steric effects involved in these reactions is critical for the pharmaceutical and chemical industries.

  1. Catalytic C-H Activation:

Catalytic C-H activation reactions are gaining prominence in the synthesis of complex organic molecules. Organometallic catalysts containing ruthenium (Ru), iridium (Ir), or rhodium (Rh) are used to selectively functionalize C-H bonds, reducing the need for pre-functionalized starting materials. Knowledge of the design of ligands and reaction conditions is crucial for the development of efficient C-H activation catalysts.

  1. Hydrogen Fuel Production:

Organometallic catalysts are also vital in the production of hydrogen fuel. Compounds based on noble metals like platinum and iridium catalyze the reduction of protons to hydrogen gas in water electrolysis and hydrogen evolution reactions. This knowledge is essential for advancing the clean energy sector.

  1. Fine Chemical Synthesis:

In the production of fine chemicals, organometallic catalysts are employed to perform various transformations, including asymmetric synthesis, carbonylation reactions, and carbon-carbon bond-forming reactions. These processes are used in the pharmaceutical and agrochemical industries to create complex, high-value compounds.

In conclusion, the understanding of organometallic compound reactions is instrumental in the industrial application of these compounds as catalysts. Their versatility and selectivity make them indispensable in a wide range of processes across industries, including organic synthesis, materials science, and sustainable energy production. Researchers and chemical engineers continually strive to optimize and develop new organometallic catalysts to meet the ever-evolving demands of industrial chemistry.

Assignment Task 5: Present the finding of a team project on a topic related to organometallic chemistry

Ladies and gentlemen, distinguished guests, and fellow colleagues, we are delighted to present the findings of our team project on the topic of “Advances in Organometallic Catalysis.” Organometallic chemistry plays a pivotal role in contemporary chemical research and industry. Our project sought to investigate recent developments in organometallic catalysis and their applications, addressing their significance, challenges, and potential future directions.

Understanding Organometallic Catalysis:

We initiated our project by providing a comprehensive overview of organometallic catalysis, emphasizing its role in enhancing the efficiency and selectivity of chemical reactions. Our exploration encompassed the following areas:

  • Introduction to Organometallic Compounds: We delved into the structure and reactivity of organometallic compounds, emphasizing their distinct nature, including metal-carbon bond formation and coordination modes.
  • Catalytic Cycles: We elucidated the mechanistic aspects of organometallic catalysis, explaining how transition metals facilitate the activation of key substrates and the formation of desired products.

Recent Advances in Organometallic Catalysis:

Our project then focused on the latest breakthroughs in this field, addressing their importance and potential impact. We explored recent developments in various types of organometallic catalysis:

  • Cross-Coupling Reactions: We discussed the latest innovations in cross-coupling reactions, such as the discovery of novel ligands, reaction conditions, and their broad application in pharmaceuticals and materials science.
  • C-H Activation: We highlighted recent achievements in C-H activation reactions, showcasing the selectivity and efficiency of this catalytic approach in complex molecule synthesis.
  • Hydroformylation: We presented innovations in hydroformylation, demonstrating its significance in the production of valuable chemicals, including aldehydes, plasticizers, and detergents.
  • Green and Sustainable Catalysis: We explored advancements in green organometallic catalysis, including the development of earth-abundant metal catalysts and their role in sustainable chemistry.

Applications and Challenges:

Our team also delved into the practical applications of organometallic catalysis in various industries:

  • Pharmaceuticals: We discussed the pivotal role of organometallic catalysis in drug discovery and development, providing examples of specific reactions and drug molecules synthesized using these techniques.
  • Petrochemicals: We explored the applications of organometallic catalysis in petrochemical processes, such as polymerization reactions, impacting the production of plastics and materials.
  • Sustainable Energy: We highlighted how organometallic catalysis contributes to the development of clean energy technologies, focusing on hydrogen fuel production and catalytic C-H activation for sustainable chemical synthesis.

Future Directions and Challenges:

In our presentation, we also addressed the potential future directions of organometallic catalysis:

  • Tailored Ligand Design: We emphasized the importance of ligand design for enhancing catalyst activity and selectivity, as well as the emerging role of machine learning and computational methods.
  • Green and Sustainable Practices: We discussed the need to address challenges related to the environmental impact of organometallic catalysis, as well as the development of more sustainable and Earth-friendly approaches.

In conclusion, our team project on “Advances in Organometallic Catalysis” underscores the significance of organometallic chemistry in shaping modern chemical research and industry. Our findings provide insights into the recent breakthroughs, applications, and challenges in the field. Organometallic catalysis continues to pave the way for sustainable chemistry, innovative materials, and novel drug discovery. We look forward to witnessing further advancements and innovations in this exciting and dynamic field.

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