Ethylmagnesium bromide is a
Grignard reagent with formula , often abbreviated to , where Et is
ethyl group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry
The International Union of Pure and Applied ...
. It is widely used in the laboratory synthesis of
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
s.
Reactions
Apart from acting as the
synthetic equivalent of an ethyl anion
synthon for
nucleophilic addition, ethylmagnesium bromide may be used as a strong base to deprotonate various substrates such as
alkyne
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Acetylene
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Propyne
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1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
s:
:RC≡CH + EtMgBr → RC≡CMgBr +
EtH
In this application, ethylmagnesium bromide has been supplanted by the wide availability of
organolithium reagents.
Preparation
Ethylmagnesium bromide is commercially available, usually as a solution in
diethyl ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
or
tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
. It may be prepared in the normal manner of
Grignard reagents — by reacting
bromoethane with
magnesium
Magnesium is a chemical element; it has Symbol (chemistry), symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 ...
in
diethyl ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
:
:EtBr + Mg → EtMgBr
References
{{Reflist
Organomagnesium compounds
Ethyl compounds