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In
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, J ...
, an alkyl group is an
alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in wh ...
missing one
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...
. 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
cycloalkane In organic chemistry, the cycloalkanes (also called naphthenes, but distinct from naphthalene) are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containin ...
by removal of a hydrogen atom from a ring and has the general formula . Typically an alkyl is a part of a larger molecule. In
structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bond ...
e, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ...
, with the formula .


Related concepts

Alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effectin ...
is an important operation in refineries, for example in the production of high-octane gasoline.
Alkylating antineoplastic agent An alkylating antineoplastic agent is an alkylating agent used in cancer treatment that attaches an alkyl group (CnH2n+1) to DNA. The alkyl group is attached to the guanine base of DNA, at the number 7 nitrogen atom of the purine ring. Since ...
s are a class of compounds that are used to treat cancer. In such case, the term alkyl is used loosely. For example,
nitrogen mustard Nitrogen mustards are cytotoxic organic compounds with the chloroethylamine (Cl(CH2)2NR2) functional group. Although originally produced as chemical warfare agents, they were the first chemotherapeutic agents for treatment of cancer. Nitrogen ...
s are well-known alkylating agents, but they are not simple hydrocarbons. In chemistry, alkyl is a group, a substituent, that is attached to other molecular fragments. For example,
alkyl lithium reagent In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...
s have the empirical formula Li(alkyl), where alkyl = methyl, ethyl, etc. A ''dialkyl'' ether is an
ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again ...
with two alkyl groups, e.g., diethyl ether (O(C2H5)2).


In medicinal chemistry

In
medicinal chemistry Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with designing and developing pharmaceutical drugs. Medicinal chemistry involves the identification, synthesis and developme ...
, the incorporation of alkyl chains into some
chemical compounds A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
increases their
lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lip ...
. This strategy has been used to increase the antimicrobial activity of
flavanone The flavanones, a type of flavonoids, are various aromatic, colorless ketones derived from flavone that often occur in plants as glycosides. List of flavanones * Blumeatin * Butin * Eriodictyol * Hesperetin * Hesperidin * Homoeriodictyol * ...
s and
chalcone Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. Chemical properties Chalcones have two absorption maxima at ...
s.


Alkyl cations, anions, and radicals

Usually, alkyl groups are attached to other atoms or groups of atoms. Free alkyls occur as neutral compounds, as anions, or as cations. The cations are called
carbocation A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium , methanium and vinyl cations. Occasionally, carbocations that bear more than one positively charged carbon atom are also encount ...
s. The anions are called
carbanion In organic chemistry, a carbanion is an anion in which carbon is trivalent (forms three bonds) and bears a formal negative charge (in at least one significant resonance form). Formally, a carbanion is the conjugate base of a carbon acid: :R3 ...
s. The neutral alkyl
free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Ailments of unknown cause Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabo ...
s have no special name. Such species are usually encountered only as transient intermediates, but some are quite stable and can be "put into a bottle". Typically alkyl cations are generated using super acids, alkyl anions are observed in the presence of strong bases, and alkyl radicals are generated by a
photochemical reaction Organic photochemistry encompasses organic reactions that are induced by the action of light. The absorption of ultraviolet light by organic molecules often leads to reactions. In the earliest days, sunlight was employed, while in more modern times ...
. Alkyls are commonly observed in
mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a '' mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is u ...
of
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
s.


Nomenclature

Alkyls form
homologous series In organic chemistry, a homologous series is a sequence of compounds with the same functional group and similar chemical properties in which the members of the series can be branched or unbranched, or differ by molecular formula of and mole ...
. The simplest series have the general formula C''n''H2''n''+1. Alkyls include ''
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ...
'', (CH3·), '' ethyl'' (C2H5·), ''
propyl In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often ...
'' (C3H7·), ''
butyl In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, gi ...
'' (C4H9·), ''
pentyl Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane. In older literature, the common non-systematic name amyl was often used for the pentyl group. Conversely, the name ...
'' (C5H11·), and so on. Alkyl groups that contain one ring have the formula C''n''H2''n''−1, e.g. cyclopropyl and cyclohexyl. The naming convention is taken from
IUPAC nomenclature A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). Th ...
: These names are used to name branched chained structures, for example 3-methylpentane: The structure of 3-methylpentane is viewed as consisting of two parts. First, five atoms comprise the longest straight chain of
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...
centers. The parent five-carbon compound is named
pentane Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the ...
(highlighted blue). The methyl "substituent" or "group" is highlighted red. According to the usual rules of nomenclature, alkyl groups are included in the name of the molecule before the root, as in methylpentane. This name is, however, ambiguous, as the methyl branch could be on various carbon atoms. Thus, the name is 3-methylpentane to avoid ambiguity: The 3- is because the methyl is attached to the third of the five carbon atoms. If there is more than one of the same alkyl group attached to a chain, then the prefixes are used on the alkyl groups to indicate multiples (i.e., di, tri, tetra, etc.) This compound is known as
2,3,3-trimethylpentane 2,3,3-Trimethylpentane is a chemical compound in the family of hydrocarbons which has a formula of C8H18. It is an isomer of octane. References

{{DEFAULTSORT:Trimethylpentane, 2,3,3- Alkanes ...
. Here three identical alkyl groups attached to carbon atoms 2, 3, and 3. The numbers are included in the name to avoid ambiguity about the position of the groups, and "tri" indicates that there are three identical methyl groups. If one of the methyl groups attached to the third carbon atom were instead an ethyl group, then the name would be 3-ethyl-2,3-dimethylpentane. When there are different alkyl groups, they are listed in alphabetical order. In addition, each position on an alkyl chain can be described according to how many other carbon atoms are attached to it. The terms
primary Primary or primaries may refer to: Arts, entertainment, and media Music Groups and labels * Primary (band), from Australia * Primary (musician), hip hop musician and record producer from South Korea * Primary Music, Israeli record label Works ...
,
secondary Secondary may refer to: Science and nature * Secondary emission, of particles ** Secondary electrons, electrons generated as ionization products * The secondary winding, or the electrical or electronic circuit connected to the secondary winding i ...
,
tertiary Tertiary ( ) is a widely used but obsolete term for the geologic period from 66 million to 2.6 million years ago. The period began with the demise of the non-avian dinosaurs in the Cretaceous–Paleogene extinction event, at the start ...
, and
quaternary The Quaternary ( ) is the current and most recent of the three periods of the Cenozoic Era in the geologic time scale of the International Commission on Stratigraphy (ICS). It follows the Neogene Period and spans from 2.58 million year ...
refer to a carbon attached to one, two, three, or four other carbons respectively.


Etymology

The first named alkyl radical was ethyl, named so by
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 t ...
in 1833 from the German word "Äther" (which in turn had been derived from the Greek word "aither") (https://en.wiktionary.org/wiki/ether , i.e., the substance now known as diethyl ether) and the Greek word ύλη (
hyle In philosophy, hyle (; from grc, ὕλη) refers to matter or stuff. It can also be the material cause underlying a change in Aristotelian philosophy. The Greeks originally had no word for matter in general, as opposed to raw material suitable ...
), meaning "matter". This was followed by methyl ( Dumas and Peligot in 1834, meaning "spirit of wood") and amyl ( Auguste Cahours in 1840). The word alkyl was introduced by
Johannes Wislicenus Johannes Wislicenus (24 June 1835 – 5 December 1902) was a German chemist, most famous for his work in early stereochemistry. Biography The son of the radical Protestant theologian Gustav Wislicenus, Johannes was born on 24 June 1835 in Kl ...
in or before 1882, based on the German word "Alkoholradikale" and then-common suffix -yl.


See also

*
Alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in wh ...
*
Alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic ...
*
Alkyne \ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 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 ...
*
Aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...
*
Hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
*
IUPAC nomenclature of organic chemistry In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the '' Nomenclature of O ...


References

{{Authority control * Substituents