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In
organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and th ...
, a functional group is a
substituent A substituent is one or a group of atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that ca ...
or
moiety Moiety may refer to: * Moiety (chemistry), a part or functional group of a molecule * Moiety (kinship), either of two groups into which a society is divided * A division of society in the Iroquois government and societal structure * An Australian Ab ...
in a
molecule A molecule is an electrically Electricity is the set of physical phenomena associated with the presence and motion Image:Leaving Yongsan Station.jpg, 300px, Motion involves a change in position In physics, motion is the phenomenon ...

molecule
that causes the molecule's characteristic
chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is any substance that has mass and t ...

chemical reaction
s. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together by chemical bonds. A homonuclear molecule, m ...
s and the design of
chemical synthesis As a topic of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they unde ...
. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in
retrosynthetic analysis Retrosynthetic analysis is a technique for solving problems in the planning of organic synthesis, organic syntheses. This is achieved by transforming a target molecule into simpler precursor structures regardless of any potential reactivity/interact ...
to plan
organic synthesis Organic synthesis is a special branch of chemical synthesis As a topic of chemistry, chemical synthesis (or combination) is the artificial execution of chemical reactions to obtain one or several product (chemistry), products. This occurs by ph ...

organic synthesis
. A functional group is a group of atoms in a molecule with distinctive
chemical properties A chemical property is any of a material's properties that becomes evident during, or after, a chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substan ...
, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by
covalent bond A covalent bond is a chemical bond that involves the sharing of electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs, and the stable balance of attractive and repulsive forces between atoms, when they s ...
s. For repeating units of
polymer A polymer (; Greek ''poly- Poly, from the Greek :wikt:πολύς, πολύς meaning "many" or "much", may refer to: Businesses * China Poly Group Corporation, a Chinese business group, and its subsidiaries: ** Poly Property, a Hong Kong inc ...

polymer
s, functional groups attach to their
nonpolar In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds composed of atoms, ...
core of
carbon Carbon (from la, carbo "coal") is a with the C and 6. It is lic and —making four s available to form s. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three occur naturally, ...

carbon
atoms and thus add chemical character to carbon chains. Functional groups can also be charged, e.g. in
carboxylate A carboxylate is the conjugate base of a carboxylic acid. Carboxylate salts are salt (chemistry), salts that have the general formula M(RCOO)''n'', where M is a metal and ''n'' is 1, 2,...; ''carboxylate esters'' have the general formula R ...

carboxylate
salts (–COO), which turns the molecule into a
polyatomic ion A polyatomic ion, also known as a molecular ion, is a covalently bonded A covalent bond is a chemical bond A chemical bond is a lasting attraction between atoms, ions or molecules that enables the formation of chemical compounds. The b ...
or a
complex ion A coordination complex consists of a central atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday object ...
. Functional groups binding to a central atom in a coordination complex are called ''
ligand In coordination chemistry A coordination complex consists of a central atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by havi ...
s''. Complexation and
solvation Solvation (or dissolution) describes the interaction of solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usual ...

solvation
are also caused by specific interactions of functional groups. In the common rule of thumb "like dissolves like", it is the shared or mutually well-interacting functional groups which give rise to
solubility In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds composed of atom ...

solubility
. For example,
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrate is a disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosacc ...

sugar
dissolves in water because both share the
hydroxyl A hydroxy or hydroxyl group is a functional group with the chemical formula -OH and composed of one oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the ...
functional group (–OH) and hydroxyls interact strongly with each other. Plus, when functional groups are more
electronegative Electronegativity, symbolized as ''Chi (letter), χ'', is the tendency of an atom to attract shared electrons (or electron density) to itself. An atom's electronegativity is affected by both its atomic number and the distance at which its valence ...

electronegative
than atoms they attach to, the functional groups will become polar, and the otherwise nonpolar molecules containing these functional groups become polar and so become soluble in some
aqueous An aqueous solution is a solution Image:SaltInWaterSolutionLiquid.jpg, Making a saline water solution by dissolving Salt, table salt (sodium chloride, NaCl) in water. The salt is the solute and the water the solvent. In chemistry, a solution ...
environment. Combining the names of functional groups with the names of the parent
alkane In , an alkane, or paraffin (a historical that also has ), is an . In other words, an alkane consists of and atoms arranged in a structure in which all the s are . Alkanes have the general chemical formula C''n''H2''n''+2. The alkanes rang ...
s generates what is termed a
systematic nomenclatureA chemical nomenclature is a set of rules to generate systematic nameA systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance A chemical substance is a form of matter In classical phys ...
for naming
organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
s. In traditional nomenclature, the first carbon atom after the carbon that attaches to the functional group is called the
alpha carbon Alpha and beta carbons in the skeletal formula of benzylacetone. The carbonyl">benzylacetone.html" ;"title="skeletal formula of benzylacetone">skeletal formula of benzylacetone. The carbonyl has two β-hydrogens and five γ-hydrogens. The alpha car ...
; the second, beta carbon, the third, gamma carbon, etc. If there is another functional group at a carbon, it may be named with the Greek letter, e.g., the gamma-amine in
gamma-aminobutyric acid ''gamma-''Aminobutyric acid, or γ-aminobutyric acid , or GABA , is the chief inhibitory neurotransmitter in the developmentally mature mammalian central nervous system. Its principal role is reducing neuronal excitability throughout the nervou ...
is on the third carbon of the carbon chain attached to the carboxylic acid group. IUPAC conventions call for numeric labeling of the position, e.g. 4-aminobutanoic acid. In traditional names various qualifiers are used to label
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulas — that is, same number of atoms of each element (chemistry), element — but distinct arrangements of atoms in space. Isomerism is existence or possibil ...

isomer
s, for example, isopropanol (IUPAC name: propan-2-ol) is an isomer of n-propanol (propan-1-ol). The term
moiety Moiety may refer to: * Moiety (chemistry), a part or functional group of a molecule * Moiety (kinship), either of two groups into which a society is divided * A division of society in the Iroquois government and societal structure * An Australian Ab ...
has some overlap with the term "functional group". However, a moiety is an entire "half" of a molecule, which can be only a single functional group, but also a larger unit consisting of multiple functional groups. For example, an "aryl moiety" may be any group containing an
aromatic ring forms of benzene (top) combine to produce an average structure (bottom) In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: the ...
, regardless of how many functional groups the said aryl has.


Table of common functional groups

The following is a list of common functional groups. In the formulas, the symbols R and R' usually denote an attached hydrogen, or a
hydrocarbon In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, prop ...
side chain In organic chemistry Organic chemistry is a branch of chemistry that studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemis ...
of any length, but may sometimes refer to any group of atoms.


Hydrocarbons

Hydrocarbons are a class of molecule that is defined by functional groups called
hydrocarbyl In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons from which one hydrogen atom has been removed are functional groups called hydrocarb ...
s that contain only carbon and hydrogen, but vary in the number and order of double bonds. Each one differs in type (and scope) of reactivity. There are also a large number of branched or ring alkanes that have specific names, e.g.,
tert-butyl In organic chemistry Organic chemistry is a branch of chemistry that studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry' ...

tert-butyl
, bornyl,
cyclohexyl Cyclohexane is a cycloalkane In organic chemistry Organic chemistry is a branch of chemistry that studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding.Clayden, J.; Greeves, N. and Warr ...

cyclohexyl
, etc. Hydrocarbons may form charged structures: positively charged
carbocation A carbocation () is an ion with a positively charged carbon atom. Among the simplest examples are the methenium , methanium and Vinyl cation, vinyl cations. Occasionally, carbocations that bear more than one positively charged carbon atom are ...
s or negative
carbanionA carbanion is an anion An ion () is a particle, atom or molecule with a net electric charge, electrical charge. The charge of the electron is considered negative by convention. The negative charge of an ion is equal and opposite to charged ...
s. Carbocations are often named ''-um''. Examples are
tropylium In organic chemistry, the tropylium ion or cycloheptatrienyl cation is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry Chemistry is the scientific discipline involved with Chemical element ...
and triphenylmethyl cations and the
cyclopentadienylCyclopentadienyl can refer to * Cyclopentadienyl anion, or cyclopentadienide, ** Cyclopentadienyl complex * Cyclopentadienyl radical, • *Cyclopentadienyl cation, See also

*Pentadienyl {{Chemistry index ...

cyclopentadienyl
anion.


Groups containing halogen

Haloalkanes The haloalkanes'' known as halogenoalkanes or alkyl halides) are alkane In , an alkane, or paraffin (a historical that also has ), is an . In other words, an alkane consists of and atoms arranged in a structure in which all the s are . ...
are a class of molecule that is defined by a carbon–
halogen The halogens () are a group A group is a number A number is a mathematical object used to counting, count, measurement, measure, and nominal number, label. The original examples are the natural numbers 1, 2, 3, 4, and so forth. Numbers can ...

halogen
bond. This bond can be relatively weak (in the case of an iodoalkane) or quite stable (as in the case of a fluoroalkane). In general, with the exception of
fluorinated In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
compounds, haloalkanes readily undergo
nucleophilic substitution A nucleophilic substitution is a class of chemical reactions A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical A chemical substance is a form of ma ...
reactions or
elimination reaction Image:EliminationReactionCyclohexene.svg, frame, Elimination reaction of cyclohexanol to cyclohexene with sulfuric acid and heat An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a ...

elimination reaction
s. The substitution on the carbon, the acidity of an adjacent proton, the solvent conditions, etc. all can influence the outcome of the reactivity.


Groups containing oxygen

Compounds that contain C-O bonds each possess differing reactivity based upon the location and hybridization of the C-O bond, owing to the electron-withdrawing effect of sp-hybridized oxygen (carbonyl groups) and the donating effects of sp2-hybridized oxygen (alcohol groups).


Groups containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of
amide In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, ...

amide
s.


Groups containing sulfur

Compounds that contain sulfur exhibit unique chemistry due to their ability to form more bonds than oxygen, their lighter analogue on the periodic table. Substitutive nomenclature (marked as prefix in table) is preferred over functional class nomenclature (marked as suffix in table) for sulfides, disulfides, sulfoxides and sulfones.


Groups containing phosphorus

Compounds that contain phosphorus exhibit unique chemistry due to their ability to form more bonds than nitrogen, their lighter analogues on the periodic table.


Groups containing boron

Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as
Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty Non-bonding orbital, orbital which is capable of accepting an electron pair from a Lewis Base (chemistry), base to form a Lewis ad ...

Lewis acid
s.


Groups containing metals

Fluorine Fluorine is a chemical element with the Chemical symbol, symbol F and atomic number 9. It is the lightest halogen and exists at Standard conditions for temperature and pressure, standard conditions as a highly toxic, pale yellow Diatomic molecule ...

Fluorine
is too electronegative to be bonded to magnesium; it becomes an
ionic salt In chemistry, a salt is a chemical compound consisting of an ionic assembly of cations and anions. Salts are composed of related numbers of cations (positively electric charge, charged ions) and anions (negatively charged ions) so that the produc ...
instead.


Names of radicals or moieties

These names are used to refer to the moieties themselves or to radical species, and also to form the names of halides and substituents in larger molecules. When the parent hydrocarbon is unsaturated, the suffix ("-yl", "-ylidene", or "-ylidyne") replaces "-ane" (e.g. "ethane" becomes "ethyl"); otherwise, the suffix replaces only the final "-e" (e.g. "
ethyne Acetylene (systematic nameA systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is a ...
" becomes "
ethynylIn organic chemistry, the term ethynyl designates * An ethynyl group (HC≡C–), also designated as acetylenic group (from acetylene Acetylene ( systematic name: ethyne) is the chemical compound A chemical compound is a chemical substa ...
"). When used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a
methylene bridge In organic chemistry, a methylene bridge, methylene spacer, or methanediyl group is any part of a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five c ...
(methanediyl) has two single bonds, whereas a
methylene group In organic chemistry, a methylene group is any part of a molecule that consists of two hydrogen Hydrogen is the chemical element with the Symbol (chemistry), symbol H and atomic number 1. With a standard atomic weight of , hydrogen is th ...

methylene group
(methylidene) has one double bond. Suffixes can be combined, as in methylidyne (triple bond) vs. methylylidene (single bond and double bond) vs. methanetriyl (three double bonds). There are some retained names, such as for methanediyl, 1,x-
phenylene The chemical structure of the ''para''-phenylene group. The phenylene group (C6H4) is based on a substitution (chemistry), di-substituted benzene ring (arylene). For example, poly(p-phenylene), poly(''p''-phenylene) is a polymer built up from ''par ...

phenylene
for phenyl-1,x-diyl (where x is 2, 3, or 4), section P-56.2.1
carbyne In organic chemistry, a carbyne is a general term for any compound whose structure A structure is an arrangement and organization of interrelated elements in a material object or system A system is a group of Interaction, interacting or in ...
for methylidyne, and
trityl Triphenylmethane, or triphenyl methane, is the hydrocarbon In organic chemistry, a hydrocarbon is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that conta ...
for triphenylmethyl.


See also

* :Functional groups * Group contribution method


References


External links


IUPAC Blue Book (organic nomenclature)
*
Functional group video

Functional group synthesis
from organic-reaction.com {{Authority control Organic chemistry