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

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5
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0answers
34 views

Why do catalysts have limited turnover numbers in practice?

I quote the Wikipedia page definition for Turnover number: In other chemical fields, such as organometallic catalysis, turnover number (abbreviated TON) has a different meaning: the number of ...
0
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0answers
45 views

What is the mechanism of reduction by Li AlH4? [closed]

What is the mechanism of reduction by $\ce{LiAlH4}$ ? I get particularly confused by this hence wanted the reaction mechanism .
1
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0answers
33 views

Comparing IR stretching bands in molybdenum complexes

Why would the infrared stretching frequency of $\ce{CO}$ (which is about $2140~\mathrm{cm^{-1}}$ in gaseous form) be $1982~\mathrm{cm^{-1}}$ in $\ce{[Mo(CO)_6]}$ and even lower in ...
1
vote
1answer
66 views

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 ...
2
votes
1answer
38 views

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 ...
0
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0answers
19 views

Reducing ability of DIBAL-H

Can DIBAL-H reduce CH3COOH? Since reactivity of acetic acid will reduce after the initial formation of the complex with the Al. But DIBAL-H is considered to be an electrophilic reductant and high ...
7
votes
1answer
67 views

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: ...
0
votes
0answers
26 views

Are heterolytic dissociations barrier-less or do they have an activation energy?

When a bond is broken into ionic fragments, and I'm specifically thinking about organometallic or coordination chemistry, the two products carry opposite charges and the potential energy curve should ...
1
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0answers
28 views

A coursework question regarding synthetic ferritin models

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 ...
1
vote
1answer
69 views

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 ...
1
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0answers
46 views

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 $\frac12$. ...
2
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0answers
33 views

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 ...
2
votes
1answer
437 views

Bonding between rings and iron atom in ferrocene

How are the 10 vertical bonds in Ferrocene (sandwich structure) connected, by what type of bonds? ]1 What is the real structure of ferrocene? Concerning the 10 vertical extra long bonds?
7
votes
1answer
150 views

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 ...
0
votes
1answer
106 views

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: $\ce{H-O-R'}$ ...
0
votes
0answers
41 views

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) -> ...
2
votes
1answer
338 views

Why is cyclooctatetraene non planar but the cyclooctatetraenide anion planar?

I was reading some organometallics and I came upon the preparation of uranocene. It has two cylcooctatetraenide anions as ligands with a Uranium atom inbetween. The author has mentioned that the ...
4
votes
1answer
73 views

Triflate use in metathesis reactions

Why are triflates so widely used in coupling reactions, but not tosylates, mesylates nor nosylates?
12
votes
1answer
197 views

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 + ...
1
vote
0answers
76 views

In Corey-House synthesis, why is R2CuLi less stable than the product RCuLi? [closed]

In Corey-House synthesis why is $\ce{R_2CuLi}$ less stable than the product $\ce{RCuLi}$ ? Please note: I don't know much about coordination chemistry, so it would be helpful if someone could explain ...
12
votes
2answers
263 views

Does a Grignard reagent react with cyclohex-2-en-1-one to give the 1,2- or 1,4- product?

My attempt: The $\ce{PhMgBr}$ nucleophile attacks on the 1,2 position. But why, in this case, will it attack the 1,4 position?
3
votes
1answer
171 views

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 ...
2
votes
0answers
38 views

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 ...
-1
votes
1answer
54 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 ...
5
votes
1answer
370 views

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: A), since dry ice is ...
2
votes
0answers
40 views

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% ...
1
vote
1answer
91 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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2answers
50 views

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.
2
votes
1answer
521 views

NO linear vs bent - valence electron

I'd like to count the total valence electron of following neutral complex in the ionic counting (=donor-pair): $\ce{Cl-}$ : 6e $\ce{CH3-}$: 2e $\ce{PPh3}$: 2e gives 10e from these three ligands ...
1
vote
1answer
181 views

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 ...
4
votes
2answers
265 views

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 tri-phenyl oxide ion as my products? I ask because I know that Grignards react with ...
1
vote
1answer
106 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?
1
vote
2answers
311 views

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 ...
1
vote
1answer
61 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 ...
5
votes
1answer
636 views

dissociation rates: trans-effect rule in square planar complexes

In lecture we became an easy description of the trans-effect. A ligand $ \ L^t \ $ with a higher trans-effect as $ \ L \ $ ( cis to $ \ L^t \ $) leads to a faster dissociation of ligand $ \ L^d \ $ ...
7
votes
3answers
125 views

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 ...
1
vote
2answers
338 views

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 ...
6
votes
1answer
311 views

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.
2
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1answer
274 views

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) ...
0
votes
1answer
89 views

“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 ...
1
vote
1answer
226 views

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 ...
6
votes
1answer
258 views

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 ...
1
vote
1answer
444 views

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 ...
3
votes
1answer
64 views

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
8
votes
1answer
146 views

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 ...
0
votes
2answers
72 views

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?
2
votes
1answer
90 views

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 ...
13
votes
3answers
2k views

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 ...
10
votes
2answers
6k views

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 ...
16
votes
1answer
365 views

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 ...