Questions tagged [organometallic-compounds]

For questions relating to organic compounds which contain a bond between a carbon atom and a metal.

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What kind of bonds can form between benzene and transition metals in π-complexes?

I'm trying to draw the six π-orbitals (3 bonding, which are filled, and 3 anti-bonding) of a benzene ring when it complexes with metal d-orbitals and which metal orbitals have the correct symmetry ($\...
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What are the specific dangers associated with Grignard reagents?

I would like to know if anyone has had any specific safety-related problems with Grignard reagents. I have taught the year-long introductory Organic Chemistry sequence for about 15 years and have ...
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Why is the cyclic voltammetry of my ferrocene compound not showing a standard shape?

I am trying to set-up a new cyclic voltammetry measurement station in my lab but the results are very poor. I am using the following parameters: ...
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Synthetic ferritin models and μ notation

This is the question verbatim: Details of two synthetic models of ferritin are presented below: System 1 $$\begin{multline}\ce{Fe(OAc)2 + LiOMe ->T[in presence of $\ce{O2}$][in MeOH]\\ ...
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Corey -House synthesis vs Wurtz reaction

In Corey House synthesis the first step is formation of Alkyl Lithium. why can't we react alkyl lithium with alkyl halide to produce alkanes. Rather we choose to prepare Gilman's reagent? Does it have ...
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I'm not sure I understand the stoichiometry of this mechanism

I was going through the experimental mechanism of nickelocene synthesis, and I looked through the notes and it said that there would be $\frac12$ $\ce{NiCl2}$. I'm sort of confused by the $\frac12$. ...
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Shelf Life of Methylcyclopentadiene

We are making organometallics in the lab, but instead of just regular Cyclopentadiene dimer, we crack methylcyclopentadiene dimer to make methylcyclopentadiene. I cannot find the shelf life of ...
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Bonding between rings and iron atom in ferrocene

How are the 10 vertical bonds in Ferrocene (sandwich structure) connected, by what type of bonds? What is the real structure of ferrocene? Concerning the 10 vertical extra long bonds?
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Negative oxidation states of Si

According to List of oxidation states of the elements, silicon has a possible oxidation state of $-4$. Now, I've been looking everywhere for a compound that contains Si(-IV), but I cannot find any ...
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What are the products of the Grignard reaction with methyl-magnesium iodide?

I want to react my ketone with methylmagnesium iodide (the Grignard reagent). I then need to use a dilute acid solution to protonate the $\ce{MgI-O-R'}$ product to produce my alcohol: $\ce{H-O-R'}$ ...
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Palladium catalyst

Recently I found the following question by sam: I'm supposed to produce dry and pure oxygen using the decomposition of hydrogen peroxide with a manganese dioxide catalyst. $$\ce{2H2O2(aq) -> ...
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Regioselectivity in Ziegler–Natta polymerisation of α-olefins

Why does the Ziegler–Natta polymerization display the regioselectivity shown in the image? Internal nucleophiles (coordinated to the metal) should attack the alkene on the less substituted end, like ...
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217 views

Triflate use in metathesis reactions

Why are triflates so widely used in coupling reactions, but not tosylates, mesylates nor nosylates?
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Why do halogen-metal exchanges happen?

I'm trying to understand organometallic raegents but am stuck at halogen-metal exchanges. For example if you have $\ce{PhBr + BuLi}$ you get $\ce{PhLi + BuBr}$, I don't understand why $\ce{PhBu + ...
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What is the mechanism of formation of Grignard's Reagent?

What is the mechanism of formation of Grignard reagents? I couldn't find much in my book or on the Internet. This page says something which I am unable to understand. Why are the $2$ electrons in the $...
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Why does Pb(II) promote ligand substitution?

I have heard of an article where divalent lead $\ce{PbL2}$ ($\ce{L}$ is ligand) reacts with something (again not sure, as I dont know the article) and what it reacts with gains a ligand. In less ...
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Propose a chemical formula for the white solid that forms during the initial stages of the reaction of Sn with benzyl chloride

In my inorganic class, we carried out the synthesis of chlorotribenzyltin, $\ce{SnCl(CH2C6H5)3}$. The synthesis begins with a reflux I'll describe below: In a hood, place 2.0 g (17 mmol) of 325 mesh ...
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124 views

Are these organo-metallic compounds?

My understanding says organo-metallic = organic + metallic compunds. One already known to me is Grignard Reagent ($\ce{RMgX}$). But would you consider $\ce{NaOMe}$ or $\ce{NaCCH}$ as an ...
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Organic reaction of dry ice and Grignard reagent

Which of the following product is formed in the reaction $\ce{CH3MgBr}$ in DryIce/acid? A) $\ce{CH3COOH}$ B) $\ce{CH4}$ C) $\ce{CH3OH}$ D) $\ce{CH3CH2CHO}$ My answer is A, since dry ice is $...
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Make pure phthalocyanines from phthalocyanine dyes

We need a pure copper phthalocyanine for our experiments. Of course, we can buy it from Sigma Aldrich, but this means we'll have to wait a while. In local area we can buy only dyes which are about 98% ...
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485 views

What is the chemical composition of the grignard reagent?

What is the actual chemical composition of the grignard reagent and what is the method of preparation? Can it be prepared in college laboratories?
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Is it possible for this Iron-Carbon Compound to exist?

Can this compound be created? Where the orange is Iron and the black is Carbon.
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NO coordination linear vs bent - valence electron

I'd like to count the total valence electron of following neutral complex in the ionic counting (=donor-pair): Electron count: $$\begin{align} \ce{Cl-} : \ce{6e-} \\ \ce{CH3-}: \ce{2e-} \\ \ce{PPh3} :...
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What makes R-MgX a more reactive Grignard reagent than R-Cu?

What makes $\ce{R-MgX}$ a more reactive Grignard reagent than $\ce{R-Cu}$? Has it to do with solvation, bond enthalpy, electronegativity?
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Why do Grignard reagents react with epoxides but not THF?

THF is used as a solvent for Grignard reagents, but epoxides react with Grignard reagents. There is only a small difference between epoxides and THF, what causes the difference in reactivity towards ...
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What's wrong with using tin in medicinal chemistry?

I just read this In the Pipeline post and I was slightly confused by a statement on the use of tin. Lowe reports on this paper, which describes a synthetic route to spiro heterocycles using tin ...
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Reaction of Grignard reagents with esters

Suppose I have a phenyl Grignard and methyl benzoate. If I react the two, can I expect benzophenone and a triphenylmethoxide ion as my products? I ask because I know that Grignards react with ...
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437 views

Gilmans and carbon dioxide

I know that Grignards react with carbon dioxide to give carboxylate anions. But will Gilmans do the same? Will Gilmans react with carbon dioxide in a productive fashion?
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Grignards do transmetallation?

Grignards don't add to alkyl halides to create linear carbon extensions because Grignards do transmetallation rather than SN2 displacement of halide. Is this correct? I thought transmetallation a) ...
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144 views

Grignards and diatomic halogens

Can Grignards react with diatomic halogens as to perform an substitution reaction? I'd imagine that the first part of making the reaction work - polarizing the halogen as to prepare to pull it apart -...
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Dissociation rates: trans-effect rule in square planar complexes

In lecture, the trans-effect was described. A ligand $L^t$ with a higher trans-effect as $L$ (cis to $L^t$) leads to a faster dissociation of ligand $L^d$ (trans to $L^t$). I would expect that the ...
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Where to find common inorganic/organometallic molecules?

I'm working on a project to create a large open repository of quantum calculations, largely for teaching purposes. I can get thousands of common organic compounds easily from sources like PubChem or ...
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Relativistic effect: d-electrons in metallorganic complexes

With higher period the d-electrons of the metal are less strong bonded and therefore oxidative addition is easier for $\ce{Ir(I)}$ than for $\ce{Rh(I)}$ and much easier than for $\ce{Co(I)}$. For ...
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Removing unreacted Mg metal in a Grignard reaction

A Grignard reagant was prepared from an alkyl halide and magnesium chips, then reacted with a ketone. The resulting solution has been stirring for a few days at low temperature (0-5°C). It's now time ...
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What's the purpose of a Grignard reagent initiation?

Preface: I've read this question about water preventing an initiation from occurring. I understand why it's important to slowly add the alkyl halide to the dry ether and magnesium for exotherm ...
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Inorganic chemistry reaction mechanisms

Are there well developed reaction mechanisms in inorganic chemistry like those in organic chemistry? If yes, please suggest an easy to follow reference.
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What is the difference between the reactivity of Lead subacetate and Lead II acetate undergoing a hydrothermal process?

I am attempting to adapt a hydrothermal method for synthesizing $\ce{PbS}$ nanocrystals to my school that contains a mixture of cationic and anionic surfactants sodium dodecyl sulfate (.05 mmol, SDS) ...
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Reaction of CpFe(CO)2Cl with phenyllithium

The reaction of $\ce{(C5H5)Fe(CO)2Cl}$ with an equimolar amount of $\ce{Li+[C6H5]-}$ gives a product. Draw its structure and apply the 18 electron rule. In a question I was given the molecular weight ...
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138 views

State of aggregation of "ate" complexes

I understand that ate complexes can result from the addition of carbanions to neutral aluminum alkyls. I was wondering what the balanced equation for this reaction is/what the structure would be in ...
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Why are organolithium and organomagnesium compounds nucleophilic in nature?

My textbook doesn't say anything about this but does say that on addition of organolithium compounds to carbon dioxide, they give ketones and not carboxylic acids like grignard reagents. This has been ...
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Molecular Oxygen in Suzuki Homocoupling

I'm curious as to the role of molecular oxygen in Suzuki homocoupling reactions, as discussed here. In a standard Suzuki cross-coupling reaction, molecular oxygen is not required. However, this paper ...
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Predicting bond-strength of metal carbonyls

The metal carbonyls (and similar organometallic compounds) involve a combination of sigma bond, a pi bond and backbonding. The bond strengths under consideration are the metal-carbon bond and the ...
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Would trans hydride ligands on a metal complex be beneficial for a catalyst?

Would trans hydride ligands on a metal complex be beneficial for a catalyst? Such as alkene metathesis or hydrodefluorination
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Do eta-4 benzene ligands participate in Diels Alder or other cycloadditions?

While refreshing myself on denticity to answer another question, I started to read about hapticity, which is the coordination of a ligand through multiple continuous atoms. A famous case is ferrocene (...
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Reaction between n-butylithium and either an aromatic bromide or an alkylbromide

What exactly happens? Does the butylithium chain add to the carbon where the bromine is attached? or do the 2 undergo halogen metal exchange?
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Overlapping oxygens in crystal structure -- what's going on?

This is a screenshot of a portion of a metal organic framework (MOF). These are two oxygens of two NMP solvent molecules. What I am wondering is why they are so close and overlapping like this. I ...
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Why do Organolithium or Grignard reagents act as nucleophiles and not as bases with aldehydes and ketones

I've read entire Chapter 14: Organometallic Compounds of Francis Carey's "Organic Chemistry" but I still didn't get an answer to my question. Quote from the book: Because of their basicity ...
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Why do Magnesium and Lithium form *covalent* organometallic compounds?

Lithium and magnesium are Group 1 and Group 2 elements respectively. Elements of these groups are highly ionic, and I've never heard of them forming significantly covalent inorganic compounds. Yet ...
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Why does benzene bend in this reaction?

From here I can see why hapticity changes here, but not why it is necessary for the benzene ring to bend. The resonance energy of benzene is pretty large, and there's no balancing increase in ...

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