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Many ethyl-containing compounds are generated by electrophilic ethylation, i.e. treatment of nucleophiles with sources of Et+.
"Ueber die Constitution des Aethers und seiner Verbindungen"
(On the composition of ethers and their compounds), ''Annalen der Pharmacie'', 9 : 1–39.) In reporting on Liebig's findings (and related work by others), Berzelius coined the names "methyl" and "ethyl" for the "radicals" CH3 and C2H5, respectively. From Jacob Berzelius, ''Årsberättelsen om framsteg i fysik och kemi'' nnual report on progress in physics and chemistry(Stockholm, Sweden: P.A. Norstedt & Söner, 1835)
p. 376
''"Man får då ge namn åt etherradikalerna; man kan kalla den äldre C4H10, ''ethyl'', den nyare C2H6, ''methyl'', … "'' (One may then give names to ether radicals; one can call the older neC4H10, ''ethyl'', the newer neC2H6, ''methyl'', … ote: At that time, chemists used the wrong atomic masses (e.g., 6 for carbon instead of 12); hence the coefficients shown here must be divided by two. In his translation into German of Berzelius' report, the German chemist Friedrich Wöhler transliterated "ethyl" as "Aethyl". (See: Jöns Jacob Berzelius with Friedrich Wöhler, trans., ''Jahresbericht über die Fortschritte der physischen Wissenschaften'' (Annual report on the progress of the physical sciences), 15 :
381.
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...
, an ethyl group (abbr. Et) is an alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen.
The term ''alkyl'' is intentionally unspecific to include many possible substitutions.
An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...
substituent with the formula , derived from ethane
Ethane ( , ) is an organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petroc ...
(). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
's nomenclature of organic chemistry
''Nomenclature of Organic Chemistry'', commonly referred to by chemists as the ''Blue Book'', is a collection of recommendations on organic chemical nomenclature published at irregular intervals by the International Union of Pure and Applied C ...
for a saturated two-carbon moiety
Moiety may refer to:
Chemistry
* Moiety (chemistry), a part or functional group of a molecule
** Moiety conservation, conservation of a subgroup in a chemical species
Anthropology
* Moiety (kinship), either of two groups into which a society is ...
in a molecule, while the prefix "''eth-''" is used to indicate the presence of two carbon atoms in the molecule.
Ethylation
Ethylation is the formation of a compound by introduction of the ethyl group. The most widely practiced example of this reaction is the ethylation of benzene with ethylene to yieldethylbenzene
Ethylbenzene is an organic compound with the formula . It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermedia ...
, a precursor to styrene
Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...
, which is a precursor to polystyrene. Approximately 24.7 million tons of ethylbenzene were produced in 1999.
::
Many ethyl-containing compounds are generated by electrophilic ethylation, i.e. treatment of nucleophiles with sources of Et+. Triethyloxonium tetrafluoroborate
Triethyloxonium tetrafluoroborate is the organic oxonium compound with the formula CH3CH2)3OF4. It is often called Meerwein's reagent or Meerwein's salt after its discoverer Hans Meerwein. Also well known and commercially available is the relat ...
t3OF4 is such a reagent. For good nucleophiles, less electrophilic reagents are employed, such as ethyl halides.
Stereochemistry
In unsymmetrical ethylated compounds, the methylene protons in the ethyl substituent are diastereotopic. Chiral reagents are known to stereoselectively modify such substituents.Etymology
The name of the group is derived from the Aether, the first-born Greek elemental god of air (and at that time a general term for any highly volatile compound) and " hyle", referring to "stuff". The name "ethyl" was coined in 1835 by the Swedish chemist Jöns Jacob Berzelius.In 1834, the German chemistJustus Liebig
Justus Freiherr von Liebig (12 May 1803 – 20 April 1873) was a German scientist who made major contributions to agricultural and biological chemistry, and is considered one of the principal founders of organic chemistry. As a professor at the ...
had argued that the group C2H5 constituted a "radical" (a cluster of atoms that did not undergo changes during chemical reactions). (See: Justus Liebig (1834"Ueber die Constitution des Aethers und seiner Verbindungen"
(On the composition of ethers and their compounds), ''Annalen der Pharmacie'', 9 : 1–39.) In reporting on Liebig's findings (and related work by others), Berzelius coined the names "methyl" and "ethyl" for the "radicals" CH3 and C2H5, respectively. From Jacob Berzelius, ''Årsberättelsen om framsteg i fysik och kemi'' nnual report on progress in physics and chemistry(Stockholm, Sweden: P.A. Norstedt & Söner, 1835)
p. 376
''"Man får då ge namn åt etherradikalerna; man kan kalla den äldre C4H10, ''ethyl'', den nyare C2H6, ''methyl'', … "'' (One may then give names to ether radicals; one can call the older neC4H10, ''ethyl'', the newer neC2H6, ''methyl'', … ote: At that time, chemists used the wrong atomic masses (e.g., 6 for carbon instead of 12); hence the coefficients shown here must be divided by two. In his translation into German of Berzelius' report, the German chemist Friedrich Wöhler transliterated "ethyl" as "Aethyl". (See: Jöns Jacob Berzelius with Friedrich Wöhler, trans., ''Jahresbericht über die Fortschritte der physischen Wissenschaften'' (Annual report on the progress of the physical sciences), 15 :
381.
See also
*Functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...
References