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Topic: Grignard reaction


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  Grignard reagent - Wikipedia, the free encyclopedia
A Grignard Reagent is an alkyl - or aryl - magnesium halide.
Grignard reagents are formed by reacting alkyl or aryl halides with organomagnesium metal, conferring a negative charge on the terminal carbon, a rare occurrence.
The Grignard reaction is exothermic and because of a oxide layer present on the magnesium, the start of the reaction is sometimes delayed.
en.wikipedia.org /wiki/Grignard_reagent   (406 words)

  
 Victor Grignard - Wikipedia, the free encyclopedia
Grignard was the son of a sail maker.
Synthesis of the Grignard reagent : an organomagnesium compound (the Grignard reagent) is made reacting an organohalide (R-X, where R stands for some alkyl, acyl, or aryl radical and X is a halogen such as usually bromine or iodine) with magnesium metal dissolved in ethyl ether.
The carbon atom that is bonded to the Mg atom bonds to the carbonyl carbon atom by nucleophilic substitution, with the formation of a new compound, which is an alcohol.
en.wikipedia.org /wiki/Victor_Grignard   (312 words)

  
 Grignard reagent   (Site not responding. Last check: 2007-11-04)
A Grignard Reagant is an alkyl - or aryl - magnesium halide.
Grignard reagants undergo reactions with compounds containing carbonyl group s.
Grignard reagants are formed by reacting alkyl or aryl halides with magnesium metal.
www.serebella.com /encyclopedia/article-Grignard_reagent.html   (350 words)

  
 Encyclopedia: Grignard reagent   (Site not responding. Last check: 2007-11-04)
A chemical reaction is a process involving one, two or more substances (called reactants), characterized by a chemical change and yielding one or more product(s) which are different from the reactants.
A coupling reaction in organic chemistry is a catch-all for a range of reactions in Organometallic chemistry where two hydrocarbon radicals are coupled with the aid of a metal containing catalyst.
An organolithium reagent is a carbon nucleophile similar to a Grignard reagent.
www.nationmaster.com /encyclopedia/Grignard-reagent   (1283 words)

  
 Grignard Reaction   (Site not responding. Last check: 2007-11-04)
A Grignard reaction is prepared by adding an alkyl halide to a cold mixture of magnesium metal in an ether solvent (anhydrous, for water will react with the Grignard reagent and destroy it).
A carboxylic acid was synthesized by the addition of dry ice (CO) to the reagent and subsequent protonation of the adduct.
The reaction was carried through as discussed in the theory section, however only several crystals (white) were collected and were all used to find the melting point.
www.chemistry.emory.edu /mccormick/reports/grignard.htm   (1094 words)

  
 AllRefer.com - Grignard reagent (Organic Chemistry) - Encyclopedia
The reaction of Grignard reagents with aldehydes to form alcohols is of particular importance in the laboratory.
Because Grignard reagents are so unstable, they are generally prepared just before use by reacting an organic halide, e.g., methyl iodide, with magnesium metal in a completely dry solvent; air is usually excluded from the reaction vessel, e.g., by flushing it with nitrogen.
Grignard reagents are named after Victor Grignard, a French chemist, who received a Nobel Prize (1912) for their discovery.
reference.allrefer.com /encyclopedia/G/Grignard-r.html   (293 words)

  
 Preparation of Phenylmagnesium Bromide
The Grignard reagent is prepared by reacting magnesium metal with an alkyl or aryl halide, using an ether as solvent, equation 1.
Grignard reagents exist in a rapid equilibrium with dialkyl- or diarylmagnesium and the corresponding magnesium halide, equation 2.
The Grignard reagent is a strong base; it will remove protons from materials that are more acidic than alkanes or alkenes, i.e., water, alcohols, terminal alkynes, amines, etc. Thus, it is imperative that the bromobenzene and ether be rigorously dried (Na) prior to use.
www.bradley.edu /las/chm/Course/351/Grignardweb2.htm   (1190 words)

  
 The Grignard Reaction
In 1912, Victor Grignard received the Nobel Prize in chemistry for his work on the reaction that bears his name, a carbon-carbon bond-forming reaction by which almost any alcohol may be formed from appropriate alkyl halides and carbonyl compounds.
The Grignard reagent is easily formed by reaction of an alkyl halide, in particular a bromide, with magnesium metal in anhydrous diethyl ether.
The most effective way to lessen this side reaction is to add the bromobenzene slowly to the reaction mixture so that it will react with the magnesium and not be present in high concentration to react with previously formed Grignard reagent.
spot.pcc.edu /~gbackes/ORGANIC/CH%20242/Labs.CH242.W05/Grignard.reaction.Benzoic.Acid.htm   (1999 words)

  
 Grignard Experiment
The Grignard reaction if an example of a class of reactions in which the carbon skeleton of a molecule is modified through the formation of a new carbon-carbon bond.
The Grignard reaction is typical of a large class of "Organometallic" reactions in that the Grignard reagent acts as a source of nucleophilic carbon which forms a new carbon-carbon bond by attacking a relatively electron deficient or electropositive carbon of a second reactant.
When the reaction has started immediately add 30 ml of more anhydrous ether directly to the the reaction flask and 20 ml of anhydrous ether to the alkyl halide in the separatory funnel, and beginning the magnetic stirring of the reaction mixture.
www.sonoma.edu /users/t/trowbrda/336/grignard.html   (1006 words)

  
 Definition of Grignard reagent
Grignard reagents are formed by reacting alkyl or aryl halides with magnesium metal.
The Grignar reaction is exothermic and because of a oxide layer on the magnesium the start of the reaction is sometimes delayed.
Thus, most Grignard reactions occur in solvents such as ether or tetrahydrofuran, because the oxygen of these solvents stabilizes the magnesium reagent.
www.wordiq.com /definition/Grignard_reagent   (259 words)

  
 Grignard Reaction   (Site not responding. Last check: 2007-11-04)
The Grignard reaction is one of the characteristic reactions of carbonyl compounds.
Often reactions that look fine on paper fail to work in the laboratory, so it is important to have a back-up plan for making your target compound.
The Grignard reaction involves the nucleophilic attack of a carbanion (the Grignard reagent) on a carbonyl carbon.
webserv.sienahts.edu /~swathen/organic/grignard.html   (266 words)

  
 Safety Improvement of a Grignard Reaction Using On-Line NIR Monitoring   (Site not responding. Last check: 2007-11-04)
Grignard reactions are important in organic synthesis because this kind of process is an easy way to form very various compounds.
The Grignard reagent formed at the reactive surface of the magnesium is solubilized in the (anhydrous) ether solvent.
The NIR probe was immersed in the reaction mixture for the spectra acquisition.
pubs.acs.org /cgi-bin/jcen?oprdfk/9/i03/html/op049784h.html   (2536 words)

  
 grignard reagents
A Grignard reagent has a formula RMgX where X is a halogen, and R is an alkyl or aryl (based on a benzene ring) group.
Grignard reagents are made by adding the halogenoalkane to small bits of magnesium in a flask containing ethoxyethane (commonly called diethyl ether or just "ether").
The reactions between the various sorts of carbonyl compounds and Grignard reagents can look quite complicated, but in fact they all react in the same way - all that changes are the groups attached to the carbon-oxygen double bond.
www.chemguide.co.uk /organicprops/haloalkanes/grignard.html   (1297 words)

  
 Definition of Victor Grignard
In the first, an organomagnesium compound (the Grigard reagent) is made by the reaction of an organohalogen (R-X, where R stands for some alkyl or aryl radical and X is usually bromine) with magnesium metal dissolved in dry ethyl ether.
The Grignard reagent has the formula R-Mg-X. In the second step, a carbonyl compound (either a ketone or an aldehyde) is added to the solution containing the Grignard reagent.
The Grignard reaction is an important means of making larger organic coumpounds from smaller starting materials.
www.wordiq.com /definition/Victor_Grignard   (344 words)

  
 McGraw-Hill AccessScience: Grignard reaction   (Site not responding. Last check: 2007-11-04)
reaction between an alkyl or aryl halide and magnesium metal in a suitable solvent, usually absolute ether.
The organomagnesium halides produced by this reaction are known as Grignard reagents and are useful in many chemical syntheses.
They are named after Victor Grignard, who discovered them and developed their use as synthetic reagents, for which he received a Nobel prize in 1912.
www.accessscience.com /Encyclopedia/3/30/Est_300200_frameset.html   (136 words)

  
 [No title]
Since a Grignard reagent is very reactive, it cannot be stored for long periods of time and must therefore be synthesized before shortly before it must be used.
This reaction is exothermic and as the reaction progresses, the ether is heated past its boiling point, the condenser mounted above the reaction flask serves to reflux the ether instead of letting it all boil away.
Once the reaction nears completion, a steam bath is used to keep the ether refluxing (steam is used instead of a flame because ether is VERY flammable).
www.angelfire.com /me4/frenchguy/school/OrgII-lab3.doc   (1083 words)

  
 The Grignard Reaction: Optimizing the Preparation of Triphenylmethanol   (Site not responding. Last check: 2007-11-04)
The Grignard reaction uses magnesium metal (Mg°) to convert an electrophilic alkyl or aryl halide to a nucleophilic carbanion.
Grignard reagents, RMgX (X = Br or I), are organometallic compounds formed by oxidative addition of Mg to the carbon-halide bond.
The reaction occurs at the surface of the magnesium metal, and therefore, the surface must be clean.
www-class.unl.edu /chem254/Lab8   (1057 words)

  
 JCE 1996 (73) 1196 [Dec] Grignard Reaction of an Epoxide: A Mechanistic Study
This undergraduate experiment serves as an interesting alternative to more traditional Grignard experiments and is an excellent vehicle for a "discovery-based" experiment in which students are introduced to epoxide chemistry, share their laboratory data and make mechanistic conclusions from their experimental results.
Unlike most undergraduate Grignard experiments which are performed merely for the sake of illustrating a textbook reaction, this Grignard synthesis is performed to probe the reactivity of styrene oxide.
Grignard Reaction of an Epoxide: A Mechanistic Study J.
www.jce.divched.org /Journal/Issues/1996/Dec/abs1196.html   (238 words)

  
 Experiment 11   (Site not responding. Last check: 2007-11-04)
The reaction will not be worked up with water this week, but with an alternative electrophile, thus showing how oxygen anions may be used as nucleophiles when they are anions.
Determine the amount of Grignard reagent you will need based on a 3.0 M solution and a 2.0 M solution (You will have two separate calculations for this stage of the lab).
Be sure to record the identity of the Grignard reagent, the concentration of the Grignard reagent solution, and the volume added to your test tube.
shakti.trincoll.edu /~tmitzel/chem211fold/laboratory/lab11/lab11.htm   (453 words)

  
 Expt 04: Benzoic acid via a Grignard reaction
Grignard reagents are organomagnesium halides : R-Mg-X ( R = alkyl, vinyl, alkynl or aryl, X = Cl, Br or I) They are an example of the very important
Grignard reagents are typically prepared from the halide compound and Mg metal in a dry ether solvent such as diethyl ether or THF :
It is important that the glassware and the materials are dry and free of water because Grignard reagents are also very basic.
www.chem.ucalgary.ca /courses/353/laboratory/353expt04.html   (253 words)

  
 Victor Grignard   (Site not responding. Last check: 2007-11-04)
French chemist and corecipient, with Paul Sabatier, of the Nobel Prize for Chemistry in 1912 for his development of the Grignard reaction.
It was Barbier who had Grignard repeat some experiments on the preparation of a tertiary alcohol from a mixture of methyl heptyl ketone, magnesium, and methyl iodide.
Grignard hit upon the idea of treating the iodide with the magnesium first and carried out the reaction in ether.
www.nobel-winners.com /Chemistry/victor_grignard.html   (221 words)

  
 Exp 7: Frequently Asked Questions   (Site not responding. Last check: 2007-11-04)
In the presence of water or methanol, the Grignard reagent decomposes; the overall effect would then be the transformation of the aryl halide (or alkyl halide) to the corresponding parent hydrocarbon.
In the undergraduate laboratory, the oxygen-free atmosphere is obtained by keeping the THF-solution warm during the preparation of the Grignard reagent.
Q: Would the Grignard reagent ever react with the second oxygen of CO No. The Grignard reaction takes place at the carbon atom of CO, and not at the oxygen atoms.
www.chem.ualberta.ca /~orglabs/x63web/frames/exp07/fr_exp7_faq.html   (607 words)

  
 The Grignard Reaction: Optimizing the Preparation of Triphenylmethanol   (Site not responding. Last check: 2007-11-04)
Triphenylmethanol can be prepared by the reaction of phenylmagnesium bromide with either benzophenone (diphenyl ketone) or with methyl benzoate.
If it appears that the reaction is going too quickly, cool the round bottom flask with ice to slow the reaction.
The Grignard reagent is prepared in a dry 10 mL reaction flask fitted with a Claisen adapter.
www-class.unl.edu /chem254/Lab8/index.htm   (1057 words)

  
 Aldehydes from Grignard reagents with formic acid
Recently, a striking solvent effect of THF on Grignard reactions with acid chlorides was observed.
In the preliminary investigation, the reaction of two moles of hexylmagnesium bromide with a mole of formic acid in THF was carried out, and a satisfactory yield (72%) of heptanal was obtained.
This reaction can be carried out at room temperature as well, but stirring of the reaction mixture for two or three days is required.
www.erowid.org /archive/rhodium/chemistry/grignard.formic.html   (1288 words)

  
 Reaction of TpmenthylMgCH2CH3 with ButC(O)Me
The Grignard reaction also produced the compound whose retention time was at 35.5 and 36.0 min as a minor product.
The b-hydroxyketone 2.9 was first synthesised using organomagnesium by Victor Grignard et al [54] in 1933.
Having calculated the response factors, the yield from the reaction can be calculated by adding a known amount of pentadecane to the reaction mixture.
www.chem.ox.ac.uk /ectoc-3/results8.html   (1321 words)

  
 The Grignard Reaction   (Site not responding. Last check: 2007-11-04)
We have covered the reaction of Grignard reagents with aldehydes and ketones in lecture and now you will perform the synthesis of a tertiary alcohol in lab.
Formation of the Grignard reagent is indicated by cloudiness and a brown color to the solution.
B Reaction of the Grignard reagent with the unknown ketone
web.centre.edu /muzyka/organic/lab/Grignard.htm   (628 words)

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