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Bromoethane

 

 
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Bromoethane
 
 
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Bromoethane, also known as ethyl bromide is a chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 of the haloalkane
Haloalkane

The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide....
s group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour.

preparation of EtBr stands as a model for the synthesis of alkyl bromides in general. It is usually prepared by the addition of HBr
Hydrogen bromide

Hydrogen bromide is the diatomic molecule HydrogenBromine. Under standard conditions, HBr is a gas, but it can be liquified. The aqueous solution hydrobromic acid forms upon dissolving HBr in water....
 to ethylene:
H2C=CH2 + HBr ? H3C-CH2Br


Ethyl bromide is inexpensive and would rarely be prepared in the laboratory.






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Bromoethane, also known as ethyl bromide is a chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 of the haloalkane
Haloalkane

The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide....
s group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour.

Preparation

The preparation of EtBr stands as a model for the synthesis of alkyl bromides in general. It is usually prepared by the addition of HBr
Hydrogen bromide

Hydrogen bromide is the diatomic molecule HydrogenBromine. Under standard conditions, HBr is a gas, but it can be liquified. The aqueous solution hydrobromic acid forms upon dissolving HBr in water....
 to ethylene:
H2C=CH2 + HBr ? H3C-CH2Br


Ethyl bromide is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis include the reacting ethanol
Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
 with a mixture of hydrobromic
Hydrobromic acid

Hydrobromic acid is a strong acid acid formed by dissolving the diatomic molecule hydrogen bromide in water. It has a Acid dissociation constant of −9, making it a stronger acid than hydrochloric acid, but not as strong as hydrogen iodide....
 and sulfuric acid
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
s. An alternate route involves refluxing ethanol with phosphorus
Phosphorus

Phosphorus is the chemical element that has the symbol P and atomic number 15. The name comes from the and . A Valency nonmetal of the nitrogen group, phosphorus is commonly found in inorganic phosphate minerals....
 and bromine
Bromine

Bromine , , meaning "stench " ), is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown Volatility liquid at Standard conditions for temperature and pressure that is intermediate in reactivity between chlorine and iodine....
; phosphorus tribromide
Phosphorus tribromide

Phosphorus tribromide is a colourless liquid with the formula PhosphorusBromine3. It fumes in air due to hydrolysis and has a penetrating odour....
 is generated in situ.

Uses

In organic synthesis
Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
, EtBr is the synthetic equivalent of the ethyl carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
 (Et+) 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....
. In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl ester
Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
s, carbanion
Carbanion

A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons ....
s to ethylated derivatives, thiourea into ethylisothiouronium salts, and amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s into ethylamines.

Being a liquid at room temperature but still very volatile, EtBr is an inexpensive reagent for the preparation of ethylmagnesium bromide
Ethylmagnesium bromide

Ethylmagnesium bromide is an organomagnesium compound. Apart from acting as the synthetic equivalent of an ethyl anion synthon for nucleophilic addition, it may be used as a strong base to deprotonate various substrates such as alkynes:...
, which traditionally was used as strong base.

Safety

Halocarbons in general are potentially dangerous alkylating agents. Bromides are better alkylating agents than chlorides, thus exposure to EtBr should be minimized. EtBr is classified by the State of California as carcinogenic and a reproductive toxin.

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