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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283 views

What is the systematic name of ammonium bisoxalato cuprate (II)? [closed]

What is the systematic name of ammonium bisoxalato cuprate(II)? I already tried $\ce{(NH4)2[Cu(C2O4)2]^{2+}}$ but i am uncertain if that answer is correct.
6
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1answer
885 views

How are Grignard reagents stable in an ethereal solution? [duplicate]

I have heard of the leveling effect, which mentions that highly basic ions cannot exist in a solvent if it's acidity is high enough to be deprotonated by the base. Considering that, check out the ...
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1answer
394 views

Why does a smaller bandgap correlate to increased absorption of visible light?

I am currently involved in a project on metal organic frameworks in my AP chemistry class, and specifically their applications in $\ce{CO2}$ reduction into formate. All the explanations we can find on ...
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2answers
90 views

Is it safe to lyophilize/Freeze-dry a chelated compound?

I have a compound that consists of a metal ion chelated by a linear organic structure with assorted moieties in aqueous medium. I'd like to dehydrate this mixture fully to get solid product, but ...
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1k views

Is the term "heteroatom" reserved for exclusive elements?

From my experience, typically in organic chemistry, the implication of "hetero-atom" in some molecule is understood as B, N, O, S, P or a halogen -- or any nonmetallic element, perhaps. If one ...
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1answer
756 views

Noyori hydrogenation and the Curtin–Hammett principle

My question is relating to how the Curtin–Hammett principle applies to homogeneous hydrogenation using chiral ligands. Figure 0: An example of a quadrant diagram used as a mnemonic to predict the ...
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1k views

CO stretching frequency band in the IR spectrum for tetracarbonylnickel and tetracarbonylferrate(II)

A past exam question says: With reference to the main bonding interactions between a transition metal and a terminal $\ce{CO}$ ligand, explain whether you would expect to observe a lower $\ce{...
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1answer
429 views

Terminal Alkyne in Suzuki Coupling

I've done a very similar reaction to the one below but by TLC I observe only starting materials. It's super clear that nothing else is going on. Conditions: K3PO4, Pd(dppf)Cl2, dioxane/water, heat to ...
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2answers
2k views

Why does magnesium prefer to insert into C–Br bonds over C–Cl bonds?

In the formation of a Grignard reagent from a compound possessing both bromine and chlorine, magnesium preferentially inserts into the C–Br bond over the C–Cl bond. For example, the formation of a ...
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83 views

Synthesis of a tungsten carbene bromide from [CpW(CO)3]-

I'm currently working through past test and exam papers in order to prepare for my organometallic test at the end of the month, but unfortunately I've gotten stuck on the following question. Since I ...
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2k views

Why do heavy metals like mercury and lead have an affinity for sulfur or sulfur compounds?

Many of the heavy metals such as mercury, lead, thallium, cadmium, and arsenic exert toxic effects largely by binding to or otherwise interfering with organic sulfur compounds or groups in the body. ...
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199 views

Grignard Reagent R group [closed]

Can the R group of a Grignard reagent (RMgX) be an alkene? Also what groups can't R be?
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1answer
2k views

Does 30% hydrogen peroxide eat away at platinum?

if I soaked a platinum dish with 30% hydrogen peroxide, will it eventually eat away at it?
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156 views

Wilkinson's catalyst: why this structure?

I wonder how the structure of Wilkinson's catalyst contributes to its catalytic properties. For example, what role do the phosphine ligands play? What properties make Rh the best TM centre? Thank ...
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2answers
16k views

Why can't the reaction of grignard reagent with carboxylic acid give a ketone?

I understand that a Grignard reagent can act both as a base and a nucleophile. It acts as a base in the presence of a proton source (eg: alcohols, amine, water, etc). But when reacting with a ketone ...
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112 views

Selectivity of olefin cross-metathesis reaction

I'm looking at the reaction shown below which uses a ruthenium catalyst: I am confused because the ruthenium catalyst which is used in the reaction should be Z selective due to the features on the ...
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42 views

Are there any stable complexes where an (N-unsubstituted) imine is bound eta^2 to a (late) transition metal?

I've been looking for an example of a stable complex where a $\ce{C=N}$ is coordinated $\eta^2$ to a (late) transition metal, but could not find any. Do they exist at all? For $\ce{C=C}$ there are ...
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1answer
28k views

Reduction of alkyl halides to alkanes

For all the three parts, only methane has been given as the product in my textbook. In 1) and 2), according to the mechanism I wrote, I get both ethane and methane as products. I think both these ...
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640 views

Treatment of ketones with excess Tebbe reagent

The reaction in black below was presented in a set of lecture notes as an example of the use of the Tebbe reagent, however it's not immediately obvious (to me, at least) that the product should be the ...
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184 views

I found transition states (TS), but calculations aren't supported by experiment. Do I look for more TSs or somewhere else?

I'm using Gaussian to investigate a catalyst system. Experimental evidence showed that one of three analogues (R = phenyl, Ph), yielded a benzosultam when treated with 2,4,6-...
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57 views

Cycloaddition of Silyl Dienol Ethers with Sodium Bromodifluoroacetate: What's the scope?

I have recently came across this article "Copper(I)-Catalyzed [4 + 1] Cycloaddition of Silyl Dienol Ethers with Sodium Bromodifluoroacetate: Access to β,β‐Difluorocyclopentanone Derivatives". (Org. ...
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544 views

Sodium Naphthalenide

The sodium fusion test done in the lab for the systematic identification of a given organic compound is basically fusing sodium metal in a fusion tube, and then adding the compound in a small quantity,...
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1answer
603 views

Formation of pi-allyl Pd cation complex

(from pg. 1334 of Clayden Organic Chemistry 1st ed.) In the above reaction catalyzed by Pd, I'm not exactly sure what's going on at the second step. It says in the book that Pd is using its electrons ...
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2answers
45 views

Best reagents state for air free chemistry. Choosing halide for grignard synthesis

I am planning to synthesize a grignard and I have a choice between the iodo or chloro aryl halide. The iodo is a solid and the chloro is borderline. For my previous reaction I melted the chloro and ...
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1answer
271 views

Reaction of (RhCp*Cl2)2 with butadiene

This is the reaction that took place: This is the information from the $\ce{^1H}$ NMR spectrum: $$\begin{array}{|c|c|c|} \hline \delta \textbf{ / ppm} & \textbf{Relative intensity} & \...
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1answer
170 views

Reagents used to prepare organic ICP standards, from scratch

I am trying to figure our how I can make my own calibration standards for organic ICP analysis. I assume that I need organometallic compounds to mix with base-oil/mineral-oil to prep the standards, ...
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914 views

Iodine/ Magnesium Exchange reaction?

Traditional Grignard reagents are made by reacting alkyl halide with Magnesium metal. However, the preparation and scope of their application have been limited because of low functional group ...
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1answer
5k views

Total valence electrons in a rhodium complex

How many valence electrons does the following metal complex have? I have read that benzene donates 6 electrons to a transition metals valence electrons. Rh has 9 from itself, and H and Cl add 1 each; ...
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543 views

Why doesn't beta hydride elimination happen in alkenyl/aryl halides?

Beta hydride elimination is an important reaction in organometallic chemistry: This reaction prohibits the use of saturated alkyl halides in coupling reactions, because it can take place after ...
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546 views

What happens to the Lithium halide salt when reacting Lithium metal with alkyl halides?

In organic chemistry, I learned a lot of useful reactions but unfortunately I didn't get to try many of them first hand (what's sad is I am a Chemistry major too). I've searched the internet back and ...
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Classes of Organometallic Compounds - Where do I put Grignard Reagents?

[Note- I've already seen this question Why do Magnesium and Lithium form *covalent* organometallic compounds? as user Mithoron was kind enough to point out, but the problem that I face is different ...
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1answer
572 views

Will Sodium Amide react with Epoxides in the same manner as Grignard Reagents?

I have been unable to find the reaction anywhere on the internet so I'm assuming the answer is no, although I would like an explanation as to why. I can't seem to find any reason why it would not ...
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1answer
8k views

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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1answer
5k 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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1answer
2k views

Coordination number of carbon in methyllithium tetramer

According to J. D. Lee's Concise Inorganic Chemistry, the coordination number of carbon in $\ce{Li4(CH3)4}$ is $7$. But the structure of the tetramer is Doesn't carbon have coordination number $6$ ...
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600 views

Why do the protons in pentacarbonylmethylmanganese show up at –0.21 ppm?

The $\ce{^1H}$ NMR of $\ce{Mn(CO)5CH3}$ shows a resonance at –0.21 ppm, which has to be due to the methyl group. Why are the protons so shielded? I would have thought that all the pi backdonation ...
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486 views

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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1answer
799 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
1k 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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669 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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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 ...
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1answer
1k views

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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56 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
357 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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358 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 moles ...
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2answers
1k views

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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1answer
20k views

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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498 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
1k 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 ($\...