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Phenylmagnesium bromide

 

 
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Phenylmagnesium bromide
 
 
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Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a magnesium
Magnesium

Magnesium is a chemical element with the symbol Mg, atomic number 12, atomic weight 24.3050 and common oxidation number +2.Magnesium, an alkaline earth metal, is the ninth most abundance of the chemical elements in the universe by mass....
-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
 or tetrahydrofuran
Tetrahydrofuran

Tetrahydrofuran is a colorless, water-miscible organic liquid with low-viscosity at "room" temperature and pressure . It is a Heterocyclic compound compound with a chemical formula C4H8O, and is the fully Hydrogenation analog of the aromatic organic compound furan....
 (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph-" synthon
Synthon

A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible organic reaction operation....
.

ylmagnesium bromide is commercially available as solutions of diethyl ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
 or THF
Tetrahydrofuran

Tetrahydrofuran is a colorless, water-miscible organic liquid with low-viscosity at "room" temperature and pressure . It is a Heterocyclic compound compound with a chemical formula C4H8O, and is the fully Hydrogenation analog of the aromatic organic compound furan....
.






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Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a magnesium
Magnesium

Magnesium is a chemical element with the symbol Mg, atomic number 12, atomic weight 24.3050 and common oxidation number +2.Magnesium, an alkaline earth metal, is the ninth most abundance of the chemical elements in the universe by mass....
-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
 or tetrahydrofuran
Tetrahydrofuran

Tetrahydrofuran is a colorless, water-miscible organic liquid with low-viscosity at "room" temperature and pressure . It is a Heterocyclic compound compound with a chemical formula C4H8O, and is the fully Hydrogenation analog of the aromatic organic compound furan....
 (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph-" synthon
Synthon

A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible organic reaction operation....
.

Preparation

Phenylmagnesium bromide is commercially available as solutions of diethyl ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
 or THF
Tetrahydrofuran

Tetrahydrofuran is a colorless, water-miscible organic liquid with low-viscosity at "room" temperature and pressure . It is a Heterocyclic compound compound with a chemical formula C4H8O, and is the fully Hydrogenation analog of the aromatic organic compound furan....
. It may be prepared in the laboratory by treating bromobenzene
Bromobenzene

Bromobenzenes are a group of halocarbons formed in a substitution reaction between bromine and benzene with a hydrogen bromide by-product. The name strictly refers to monobromobenzene, a benzene with a single bromine; however it can be used to refer to a benzene containing any number of bromine molecules....
 with magnesium
Magnesium

Magnesium is a chemical element with the symbol Mg, atomic number 12, atomic weight 24.3050 and common oxidation number +2.Magnesium, an alkaline earth metal, is the ninth most abundance of the chemical elements in the universe by mass....
 metal, usually in the form of ribbon. A small amount of iodine
Iodine

Iodine , is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons....
 may be used to activate the magnesium to initiate the reaction.

Polar solvents, such as ether or THF, are required to solvate (complex) the magnesium(II) center. The solvent must be aprotic solvent
Protic solvent

In chemistry a protic solvent is a solvent that has a hydrogen atom bound to an oxygen as in a hydroxyl group or a nitrogen as in an amine group....
s since alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s and water react with phenylmagnesium bromide to give benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
. Carbonyl-containing solvents such as acetone and ethyl acetate are incompatible with the reagent.

Structure

Although phenylmagnesium bromide is routinely represented as C6H5MgBr, the molecule is more complex. The compound invariably forms an adduct
Adduct

An adduct is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components, with formation of two chemical bonds and a net reduction in bond multiplicity in at least one of the reactants....
 with two OR2 ligands from the ether or THF solvent. Thus, the Mg is tetrahedral and obeys the octet rule
Octet rule

The octet rule is a simple chemistry rule of thumb that states that atoms tend to combine in such a way that they each have eight electrons in their valence shells, giving them the same electronic configuration as a noble gas....
. The Mg-O distances are 2.01 and 2.06 Å whereas the Mg-C and Mg-Br distances are 2.2 and 2.44 Å, respectively.

Chemistry

Phenylmagnesium bromide is a strong nucleophile
Nucleophile

In chemistry, a nucleophile is a reagent that forms a chemical bond to its reaction partner by donating both bonding electrons. Because nucleophiles donate electrons, they are by definition Lewis bases ....
 as well as a strong base
Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
. It can abstract even mildly acidic protons, thus the substrate must be protected where necessary. It often adds to carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
s, such as ketones, aldehydes. With carbon dioxide, it reacts to give, after an acidic workup, benzoic acid
Benzoic acid

Benzoic acid, C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid....
.