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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4
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0answers
25 views

Further reading on photoconductivity of hemoglobin

I recently ran into this paper which describe experiments that confirm that hemoglobin is photoconductive. Finding this fact as incredible, I wanted to read up more on photoconductive properties of ...
6
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1answer
234 views

Why do aromatic compounds have an upfield shift upon coordination to metals?

Why do aromatic compounds have an upfield shift upon coordination to metals e.g. ferrocene? The 1H NMR shows a single environment at ~4.1 ppm. This is in contrast to the usual aromatic shift of ...
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36 views

Why doesn't Grignard reagent attack alkyl halides [duplicate]

When we add magnesium to alkyl halide, Grignard reagent is formed. $$\ce{R-X + Mg -> RMgX } $$ It is highly nucleophilic in nature. Now at this time the electrophilic alkyl halide is also present ...
2
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1answer
57 views

How does 1-bromo-2-fluorobenzene react with lithium amalgam? [closed]

How does this organometallic reagent react with 1-bromo-2-fluorobenzene? Does it react like Grignard reagent? If the product of this reaction is then reacted with furan, what will be the final product?...
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On the stability of methyl mercury

Question: Given that $\ce{Zn, Hg}$ are in the same group, how to explain that $\ce{Hg(CH3)}$ is stable but $\ce{Zn(CH3)}$ is unstable and $\ce{Hg(CH3)Cl}$ is stable? $\ce{Hg(CH3)}$ seems to have an ...
3
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1answer
95 views

Will ferrocene undergo electrophilic aromatic substitution?

Ferrocene has two structure 1 and 2.It is bonded to an aromatic ion cyclopentadienyl anion.Aromatic species such as benzene , cyclopentadienyl anion undergo electrophilic aromtic substitutions. Then,...
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95 views

Can pi backdonation occur on non-metal centers?

The common example of back-donation is the interaction of a CO molecule with a metal center (d-orbitals) on a surface. Can a similar mechanism occur between CO and a non-metal center, like oxygen on ...
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23 views

Alkyl insertion with cobalt and CO

Reaction of $\ce{(Cp)Co(Me)2(CO)}$ in the presence of excess $\ce{CO}$ yields two different organic products, $\ce{A}$ and $\ce{B}.$ The only metal-containing product is $\ce{(Cp)Co(CO)2}.$ The IR ...
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67 views

How can organocuprates generated with catalytic Cu(I) be competitive in 1,4-addition to an enone?

Organocopper compounds (e.g. $\ce{LiCuR_2}$) are often prepared from an organolithium or Grignard reagent when a soften nucleophile is needed, such as for a conjugate addition to an $\alpha,\beta$-...
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18 views

Will lead bind to dissolved polymer (Kapton) monomers?

We are attempting to determine the concentration of lead impurities in Kapton. Essentially we need to extract lead in the tape polymer Kapton (structure seen below); The amount of lead in the tape is ...
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29 views

Electron-donating trends for ligands bound to metal complexes

Imagine an inorganic complex with a bunch of terminal ligands. All else the same, would $\ce{F-}$ or $\ce{Br-}$ ligands be more electron-donating and why? Of course, in terms of $\mathrm{p}K_{\mathrm{...
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5k 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 ...
8
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1answer
123 views

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 ...
2
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1answer
50 views

N-heterocyclic carbene metal complexes. Question about the delocalization of the nitrogen lone pairs

I am wondering why nitrogen lone pairs are delocalized in NHC metal complexes. What I can think of is, when complex is formed, plus charge is formed on the carbon atom and therefore delocalization ...
4
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1answer
1k views

Grignard Reagent in THF vs in Diethyl ether

While learning about the Grignard reagent I was taught this by my teacher, but I couldn’t justify why it was so.. I cannot see how Grignard reagent would react differently in basically an ethereal ...
13
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2answers
659 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 ...
14
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2answers
144 views

Mechanism of a Gold catalyzed organometallic reaction: Confusion regarding the last step

I needed to draw the reaction mechanism for this reaction: So, after consulting some literature I drew this mechanism: But, I am not sure about the last step. Does the $\ce{H+}$ just substitute the $...
3
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1answer
691 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 $6$ ...
2
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1answer
87 views

Is an alcohol-based spray cleaner ok for cleaning an aluminum heat exchanger?

Simple alcohols such as ethanol can, apparently, corrode aluminum. However, this corrosion reaction seems to be very slow at room temperature and below. Is an ethanol based, non-foaming spray cleaner, ...
2
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0answers
161 views

Why does LDA solution gradually turn dark brown?

LDA (lithium diisopropylamide) solution in THF/hexane gradually turns red-brown liquid. Especially commercially available one is extremely dark red-brown. What makes it brown? I've searched online ...
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2answers
4k 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 ...
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184 views

Reaction of grignard with beta Keto ester [closed]

A reaction takes place between $\ce {CH3COCH2COOC2H5}$ with 4-chlorophenyl magnesium bromide, followed by acidic work-up. What will be major product of the reaction? Would the product be the same as ...
2
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1answer
15k 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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49 views

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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24 views

How to calculate the magnetic exchange coupling in a charged radical complex?

I have a neutral complex with two magnetic centers. For this case it is easy to calculate the exchange coupling as the broken symmetry state is converged properly. But when I am making the complex ...
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149 views

What makes dimethylmercury ((CH3)2Hg) so penetrative through latex and human skin?

I've read the story of Karen Wetterhahn and how she was poisoned and died from two drops of dimethylmercury that accidentally fell on her latex glove, and I was wondering what is the chemical ...
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1answer
54 views

Is it possible to have a ferrocenol?

I'm specifically talking about having a hydroxy- group on the ferrocene ring. Is it simply impossible because the ring is anionic? I haven't seen any hydroxyferrocene molecules available online. (...
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1answer
578 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 ...
2
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0answers
319 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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142 views

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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841 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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1answer
39 views

How do we know cyclopentadienylmolybdenum tricarbonyl occurs as a dimer?

Cyclopentadienylmolybdenum tricarbonyl, $\ce{MoC8H5O3}$, dimerizes to form the cyclopentadienylmolybednum tricarbonyl dimer, $\ce{(MoC8H5O3)2}$. $\hspace{3cm}$ How was it discovered that it does ...
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71 views

Do Sodium Alkynides react with esters in the same way that Grignard reagents do?

We know that Sodium alkynides react with aldehydes and ketones like Grignard reagents. But do they behave the same way with esters?
2
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1answer
127 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, ...
10
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1answer
121 views

How can the solid state structure of cyclopentadienyllithium be explained?

In the solid state, LiCp adopts a polymeric multidecker structure where Li atoms are sandwiched between two Cp rings (shown in this diagram from Organometallics 1997, 16 (17), 3855–3858): If we ...
17
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1answer
311 views

How to name this quintuply-bonded chromium dimer?

Depicted below is a chromium compound with a metal–metal quintuple bond. It boasts two identical bridging ligands, derivatives of 1,3-diphenylbenzene. The aim of this question is to figure out the ...
10
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1answer
594 views

Mechanism of lithium-halogen exchange of primary alkyl iodide

On Clayden's page 190 this reaction is given for preparation of organometallics: What is the mechanism of this reaction? I expected the "almost carboanion" part of the $\ce{t-BuLi}$ to attack as a ...
38
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1answer
910 views

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 ...
11
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1answer
241 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 ...
7
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1answer
7k 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 ...
6
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1answer
2k views

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 ...
2
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1answer
2k views

How to electron count bridging ligands?

Although I am okay with rationalising bridging halides and $\mu$-2 CO I can't seem to figure out others, including $\mu$-2 hydride, CN- and NO. When considering the electron count of bridging ligands,...
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69 views

What does unactivated, activated and deactivated aryl chloride means in cross-coupling reactions?

When I read this literature https://pubs.acs.org/doi/pdf/10.1021/jo990408i, it used unactivated aryl chloride for Buchwald-Hartwig amination. What does unactivated, activated and deactivated aryl ...
4
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2answers
371 views

How does the Wurtz reaction produce alkynes?

Wikipedia mentions that alkynes can be produced from geminal dihalides through the Wurtz reaction. However, I am unsure of the reaction mechanism for this reaction. I have not been able to find any ...
2
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1answer
83 views

What is the product of magnesium reacting with carbon?

$$\ce{Mg + C -> X}$$ $$\ce{X + H2O -> Y}$$ Determine unknowns X and Y. Now the problem is I think the answer should be $\ce{X=MgC2}$ and $ \ce{Y=C2H2 + Mg(OH)2}$. But the given answer was ...
2
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1answer
103 views

One-pot synthesis of pyrazole [closed]

I am trying to follow a published paper. It is a one-pot synthesis of pyrazole from a ketone and and acid chloride via a diketone intermediate. Here is the produre from the paper: General Procedure:...
3
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0answers
396 views

Mechanism for reaction of an allene with the Grignard Reagent(RMgX)

How does the Grignard Reagent($\ce{RMgX}$) react with an allene $\ce{CH_2=C=CH_2}$ and what are the products formed? This is exactly what I tried to do. Any help will be appreciated.
5
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1answer
471 views

Why are 3 equivalents of organolithium needed in synthesis of ketone from carboxylic acid?

For the reaction of a carboxylic acid and organolithium reagents to synthesise a ketone, Clayden's, on p 219, mentions: Notice that three equivalents of organolithium are needed in this reaction: ...
7
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1answer
5k 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 is A, since dry ice is $...
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1answer
300 views

electron counting for transition metal-oxo ligand compound

Using donor-pair method, how many electrons would an oxo ($O^{2-}$) ligand contribute? I cannot decide if it is 2 or 4.