Questions tagged [organometallic-compounds]
For questions relating to organic compounds which contain a bond between a carbon atom and a metal.
212
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2
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Selectivity in Suzuki coupling of 2,4-dichloropyrimidine
I've seen many papers (see e.g. Synthesis 2010, 16, 2721–2724) in which the 4-chloro group of 2,4-dichloropyrimidine is selectively reacted under Suzuki coupling conditions. Is there any way where ...
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7
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1
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Role of Cu in Corey-House synthesis
What does $\ce{Cu}$ do? And why do we need it? Can we not do $\mathrm{S_N}2$ without it? And is there any other metal that can help in this? Maybe something like $\ce{Ag}$? I'm guessing this because ...
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1
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Kolbe's electrolysis method for getting alkanes
It involves the electrolysis of "Sodium and Potassium salts of Carboxylic Acids". Why only Sodium and Potassium? Will some other metal like Li, Mg, Zn etc. not work? As long as the element is a better ...
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2
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0
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694
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Trends in the covalency of bonding across the transition metals
I am under the impression that the covalent character in the bonding of transition metal compounds increases across a group; in fact I think this is why they're called transition metals (a transition ...
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1
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Alkane deprotonation by organolithiums
Butyllithium isomers are all stored in alkane solvents. Theoretically, equilibrium should (given enough time) lead to formation of mostly n-hexyllithium in the case of n-BuLi stored in (mostly) n-...
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Can 0-Carborane be stored at room temperature?
I am a physics post-doc at Oak Ridge National Lab (with a bit more training in chem than the average physicist). I ordered a small sample of o-Carborane from Sigma-Aldrich to test for doping liquid ...
- 295
1
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1
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What would happen if the reaction of reduction of carboxylic acids by LiAlH4 is carried out in alcohol?
Which is the intermediate compound in the reduction of carboxylic acids by $\ce{LiAlH4}$ and what would happen if the reduction of carboxylic acids is carried out in alcohol?
From my knowledge I know ...
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0
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How would the relative rate of reduction of carboxylic acid be if the catalyst used is LiAlH3D?
How would the relative rate of reduction of carboxylic acid be if the catalyst used is LiAlH3D , LiAlH2D2 , LiAlHD3 , LiAlD4 just thought about it while revising the reaction mechanism of carboxylic ...
- 513
2
votes
1
answer
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Is 98%+ purity Reagent Grade Ca-EDTA powder as safe to use as USP Grade in the body? [closed]
Is $98\%+$ purity reagent grade $\ce{Ca}$-EDTA powder as safe to use as USP grade in the body? Or, does the reagent grade have unsafe impurities that USP grade would not have even though they are the ...
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0
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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 moles ...
- 967
2
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2
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Why does mercury in mercuric acetate have a lone pair?
The configuration of mercury ends with $6s^{2}$. In mercuric acetate, mercury is in the +2 oxidation state, so does it still have a lone pair?
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Is there a reaction between ethanol and aluminum?
Is there a potential reaction that would occur between ethanol and aluminum? If so, would it potentially create anything toxic?
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0
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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 $\ce{[Mo(CO)3(η^6$\...
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1
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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 ($\...
- 41
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1
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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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0
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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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1
answer
5k
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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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0
answers
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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$. ...
- 31
2
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0
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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 ...
- 31
2
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3
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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?
13
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2
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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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1
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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) -> ...
- 11
5
votes
0
answers
174
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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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votes
1
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234
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Triflate use in metathesis reactions
Why are triflates so widely used in coupling reactions, but not tosylates, mesylates nor nosylates?
- 14.2k
16
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1
answer
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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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answer
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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 $...
- 3,765
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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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19
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1
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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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0
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1
answer
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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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votes
1
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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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2
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0
answers
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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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524
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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?
2
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2
answers
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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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0
answers
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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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answer
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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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1
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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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1
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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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2
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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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1
answer
560
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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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2
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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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1
vote
1
answer
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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 -...
- 18.4k
6
votes
1
answer
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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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11
votes
3
answers
249
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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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38
votes
1
answer
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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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2
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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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2
votes
2
answers
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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 ...
- 337
12
votes
1
answer
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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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1
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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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