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

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Why does magnesium form covalent bonds with carbon?

According to my professor, magnesium and lithium form covalent bonds with carbon but calcium does not. He did not elaborate. Why is this so? The electronegativities are: Mg - 1.31 Li - 0.98 Ca - 1 ...
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33 views

Why is BuLi a better nucleophile than base?

In Carey, Sundberg Advanced Organic Chemistry it is written: The relative slowness of the abstraction of protons from carbon acids by organolithium reagents is probably also due to the compact ...
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2answers
65 views

Why does Mn(CO)5(CH3) have a 1H NMR peak at -0.21 ppm?

I would have thought that all the pi backdonation from the Mn to the carbonyl would reduce the electron density on the CH3 increasing the chemical shift.
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21 views

Number of stereo-isomeric products?

This is the question:- And this is my approach:- As you can see, according to my solution, the answer should be 2. But the answer is 4. Also, I have doubt in the first step that whether the anion ...
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1answer
143 views

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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1answer
74 views

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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23 views

IR spectrum of an organometallic compound [closed]

In a solution IR of [CpFe(CO)2]2 (Cp = cyclopentadienyl), 3 peaks are observed. These are: 2006, 1962 and 1794 cm-1. Questions: 1. Why are there 3 peaks (hint: molecular symmetry)? 2. What does each ...
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12 views

Fischer Carbene complexes with metal in high oxidation state

One of the main criteria for a Fischer Carbene complex is that the metal should be in low oxidation state which means that it should be electron rich. But it should also have auxillary pi acceptor ...
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32 views

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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1answer
146 views

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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33 views

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 ...
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1answer
112 views

What would happen if the reaction of reduction of carboxylic acids by LiAlH4 is carried out in alcohol

Question 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 ...
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20 views

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 ...
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1answer
46 views

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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62 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 ...
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51 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 $\ce{[Mo(CO)3(η^6$\...
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1answer
112 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 ($\...
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1answer
114 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 ...
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33 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 ...
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1answer
207 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: ...
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28 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 ...
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33 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 MeOH]\\...
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1answer
617 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 ...
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49 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 $\frac12$. ...
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39 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 ...
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1answer
946 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? What is the real structure of ferrocene? Concerning the 10 vertical extra long bonds?
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1answer
203 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 ...
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1answer
210 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: $\ce{H-O-R'}$ ...
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48 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) -> ...
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1answer
777 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 ...
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1answer
88 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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1answer
435 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 + ...
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85 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 ...
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427 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?
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1answer
252 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 $...
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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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1answer
56 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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554 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 $\ce{...
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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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1answer
132 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
54 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.
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1answer
856 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 ...
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1answer
298 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 ...
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439 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 ...
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131 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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384 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 transmetallation a)...
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1answer
71 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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1answer
854 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 \ $ (...
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135 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 ...
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493 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 ...