Functional group

Benzyl acetate has an ester functional group (in red), an acetyl moiety (circled with dark green) and a benzyloxy moiety (circled with light orange). Other
divisions can be made.

In organic chemistry, functional groups are specific groups (moieties) of atoms or bonds within molecules that are responsible for the
characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction(s)
regardless of the size of the molecule it is a part of.[1][2] This allows for systematic prediction of chemical reactions and behavior of chemical
compounds and design of chemical syntheses. Furthermore, the reactivity of a functional group can be modified by other functional groups
nearby. In organic synthesis, functional group interconversion is one of the basic types of transformations.
The atoms of functional groups are linked to each other and to the rest of the molecule by covalent bonds. Functional groups can also be
charged, e.g. in carboxylate salts (–COO−), which turns the molecule into a polyatomic ion or a complex ion. Functional groups binding to a
central atom in a coordination complex are called ligands. Complexation and solvation is 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. For example, sugar dissolves in water because both share the hydroxyl functional group (–OH) and hydroxyls interact strongly
with each other.
Combining the names of functional groups with the names of the parent alkanes generates what is termed a systematic nomenclature for
naming organic compounds. In traditional nomenclature, the first carbon atom after the carbon that attaches to the functional group is called
the alpha carbon; 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 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 isomers; for example, isopropanol (IUPAC name: propan-2-ol) is an isomer of n-propanol (propan-1-ol).

Hydrocarbons[edit]
Functional groups, called hydrocarbyl, 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.
Chemical class Group Formula Structural Formulae Prefix Suffix Example

Alkane Alkyl R(CH2)nH alkyl- -ane

Ethane

Alkene Alkenyl R2C=CR2 alkenyl- -ene

Ethylene
(Ethene)

Alkyne Alkynyl RC≡CR' alkynyl- -yne

Acetylene
(Ethyne)
 RC6H5
Benzene derivative Phenyl phenyl- -benzene
RPh

Cumene
(Isopropylbenzene)

There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc. Hydrocarbons
may form charged structures: positively charged carbocations or negative carbanions. Carbocations are often named -um. Examples
are tropylium and triphenylmethyl cations and the cyclopentadienyl anion.

Groups containing halogen[edit]

Haloalkanes are a class of molecule that is defined by a carbon–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 compounds, haloalkanes readily
undergo nucleophilic substitution reactions or elimination reactions. The substitution on the carbon, the acidity of an adjacent proton, the
solvent conditions, etc. all can influence the outcome of the reactivity.

Chemical Structural
Group Formula Prefix Suffix Example
class Formula
haloalkane halo RX halo- alkyl halide Chloroethane
(Ethyl chloride)

fluoroalkane fluoro RF fluoro- alkyl fluoride

Fluoromethane
(Methyl
fluoride)

chloroalkane chloro RCl chloro- alkyl chloride

Chloromethane
(Methyl
chloride)

bromoalkane bromo RBr bromo- alkyl bromide

Bromomethane
 (Methyl
bromide)

iodoalkane iodo RI iodo- alkyl iodide

Iodomethane
(Methyl iodide)

Groups containing oxygen[edit]

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).

Structural
Chemical class Group Formula Prefix Suffix Example
Formula

Alcohol Hydroxyl ROH hydroxy- -ol

Methanol

-oyl- (-COR')
Ketone Carbonyl RCOR' or -one
oxo- (=O) Butanone
(Methyl ethyl ketone)
 formyl- (-COH)
Aldehyde Aldehyde RCHO or -al
oxo- (=O)
Acetaldehyde
(Ethanal)

carbonofluoridoyl-
carbonochloridoyl-
Acyl halide Haloformyl RCOX -oyl halide
carbonobromidoyl-
carbonoiodidoyl- Acetyl chloride
(Ethanoyl chloride)

(alkoxycarbonyl)ox
Carbonate Carbonate ester ROCOOR' alkyl carbonate Triphosgene
y-
(bis(trichloromethyl)
carbonate)

Carboxylate Carboxylate RCOO− carboxy- -oate

Sodium acetate
(Sodium ethanoate)
Carboxylic acid Carboxyl RCOOH carboxy- -oic acid
Acetic acid
(Ethanoic acid)

alkanoyloxy-
Ester Ester RCOOR' or alkyl alkanoate
Ethyl butyrate
alkoxycarbonyl
(Ethyl butanoate)

Methoxy Methoxy ROCH3 methoxy-

Hydroperoxide Hydroperoxy ROOH hydroperoxy- alkyl hydroperoxide

tert-Butyl
hydroperoxide

Peroxide Peroxy ROOR' peroxy- alkyl peroxide

Di-tert-butyl peroxide

Ether Ether ROR' alkoxy- alkyl ether Diethyl ether

(Ethoxyethane)

Hemiacetal Hemiacetal RCH(OR')(OH) alkoxy -ol -al alkyl hemiacetal

Hemiketal Hemiketal RC(ORʺ)(OH)R' alkoxy -ol -one alkyl hemiketal

 Acetal Acetal RCH(OR')(OR") dialkoxy- -al dialkyl acetal

Ketal (or Acetal Ketal (or Acetal

RC(ORʺ)(OR‴)R' dialkoxy- -one dialkyl ketal
) )

Orthoester Orthoester RC(OR')(ORʺ)(OR‴) trialkoxy-

Methylenediox
Heterocycle PhOCOPh methylenedioxy- -dioxole 1,2-
y
Methylenedioxybenzen
e
(1,3-Benzodioxole)
Orthocarbonate Orthocarbonate C(OR)(OR')(ORʺ)(OR tetraalkylorthocarbona
tetralkoxy-
ester ester ″) te
Groups containing nitrogen[edit]
Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.
Chemical
Group Formula Structural Formula Prefix Suffix Example
class

carboxamido-
Amide Carboxamide RCONR2 or -amide
carbamoyl- Acetamide
(Ethanamide)

Primary
RNH2 amino- -amine
amine
Methylamine
(Methanamine)

Amines Secondary
R2NH amino- -amine
amine
Dimethylamine

Tertiary
R3N amino- -amine
amine
Trimethylamine
 4°
ammonium R4N+ ammonio- -ammonium
ion
Choline

Primary
RC(=NH)R' imino- -imine
ketimine

Secondary
imino- -imine
ketimine

Imine

Primary
RC(=NH)H imino- -imine
aldimine Ethanimine

Secondary
RC(=NR')H imino- -imine
aldimine
 Imide Imide (RCO)2NR' imido- -imide

Succinimide
(Pyrrolidine-2,5-dione)

Azide Azide RN3 azido- alkyl azide

Phenyl azide
(Azidobenzene)

Azo Azo
RN2R' azo- -diazene
compound (Diimide) Methyl orange
(p-dimethylamino-
azobenzenesulfonic acid)
 Cyanate ROCN cyanato- alkyl cyanate

Methyl cyanate
Cyanates

Isocyanate RNCO isocyanato- alkyl isocyanate

Methyl isocyanate

nitrooxy-,
Nitrate Nitrate RONO2 alkyl nitrate
nitroxy-
Amyl nitrate
(1-nitrooxypentane)

alkanenitrile
Nitrile RCN cyano-
alkyl cyanide
Nitrile Benzonitrile
(Phenyl cyanide)

alkaneisonitrile
Isonitrile RNC isocyano-
alkyl isocyanide
Methyl isocyanide

Nitrite Nitrosooxy RONO nitrosooxy- alkyl nitrite

Isoamyl nitrite
(3-methyl-1-
nitrosooxybutane)
 Nitro
Nitro RNO2 nitro-
compound
Nitromethane

Nitroso nitroso-
Nitroso RNO
compound (Nitrosyl-)
Nitrosobenzene

Oxime Oxime RCH=NOH Oxime

Acetone oxime
(2-Propanone oxime)

4-pyridyl
(pyridin-4-yl)
Pyridine 3-pyridyl
Pyridyl RC5H4N -pyridine
derivative (pyridin-3-yl)
2-pyridyl Nicotine
(pyridin-2-yl)

Groups containing sulfur[edit]

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.
Chemical Structural
Group Formula Prefix Suffix Example
class Formula

sulfanyl-
Thiol Sulfhydryl RSH -thiol
(-SH) Ethanethiol

Sulfide substituent sulfanyl-

Sulfide RSR' di(substituent) sulfide
(Thioether) (-SR')
(Methylsulfanyl)methane (prefix) or
Dimethyl sulfide (suffix)

substituent disulfanyl-
Disulfide Disulfide RSSR' di(substituent) disulfide
(-SSR')
(Methyldisulfanyl)methane (prefix) or
Dimethyl disulfide (suffix)

-sulfinyl-
Sulfoxide Sulfinyl RSOR' di(substituent) sulfoxide
(-SOR')
(Methanesulfinyl)methane (prefix) or
Dimethyl sulfoxide (suffix)
 -sulfonyl-
Sulfone Sulfonyl RSO2R' di(substituent) sulfone
(-SO2R')
(Methanesulfonyl)methane (prefix) or
Dimethyl sulfone (suffix)

sulfino-
Sulfinic acid Sulfino RSO2H -sulfinic acid
(-SO2H)
2-Aminoethanesulfinic acid

sulfo-
Sulfonic acid Sulfo RSO3H -sulfonic acid
(-SO3H)
Benzenesulfonic acid

thiocyanato-
Thiocyanate RSCN substituent thiocyanate
(-SCN)
Phenyl thiocyanate
Thiocyanate

isothiocyanato-
Isothiocyanate RNCS substituent isothiocyanate
(-NCS)
Allyl isothiocyanate
 -thioyl-
(-CSR')
Thioketone Carbonothioyl RCSR' or -thione
sulfanylidene- Diphenylmethanethione
(=S) (Thiobenzophenone)

methanethioyl-
(-CSH)
Thial Carbonothioyl RCSH or -thial
sulfanylidene-
(=S)

Thioester

carbodithioic
acid

Groups containing phosphorus[edit]

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

Chemical Structural
Group Formula Prefix Suffix Example
class Formula
 Phosphine Phosphin
R3P phosphanyl- -phosphane
(Phosphane) o
Methylpropylphosphane

Phosphonic Phospho substituentphospho

phosphono-
acid no nic acid
Benzylphosphonic acid

phosphonooxy- Glyceraldehyde 3-phosphate (suffix)

Phosphat or substituentphospha
Phosphate
e O-phosphono- (phospho- te
)

O-Phosphonocholine (prefix)
(Phosphocholine)

di(substituent) DNA
[(alkoxy)hydroxyphosphoryl] hydrogen phosphat
oxy- e
Phosphodies Phosphat HOPO(O or
O-
or
ter e R)2 O-[(2-Guanidinoethoxy)hydroxyphosphoryl]-L-serine
[(alkoxy)hydroxyphosphoryl] phosphoric acid
- di(substituent) este (prefix)
r (Lombricine)

Groups containing boron[edit]

Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as Lewis acids.
 Chemical Structural
Group Formula Prefix Suffix Example
class Formula

substituent
Boronic acid Borono RB(OH)2 Borono-
boronic acid

Phenylboronic acid

substituent
O-
Boronic ester Boronate RB(OR)2 boronic acid
[bis(alkoxy)alkylboronyl]-
di(substituent) ester

di(substituent)
Borinic acid Borino R2BOH Hydroxyborino-
borinic acid

di(substituent)
Borinic ester Borinate R2BOR O-[alkoxydialkylboronyl]- borinic acid
substituent ester
Diphenylborinic acid 2-aminoethyl
ester
(2-Aminoethoxydiphenyl borate)
Names of radicals or moieties[edit]
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" becomes "ethynyl").[4]
Note that when used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a methylene
bridge (methanediyl) has two single bonds, whereas a 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 single bonds).
There are some retained names, such as methylene for methanediyl, 1,x-phenylene for phenyl-1,x-diyl (where x is 2, 3, or 4),[5] carbyne for
methylidyne, and trityl for triphenylmethyl.

Chemical class Group Formula Structural Formula Prefix Suffix Example

Methyl group
Single bond R• Ylo-[6] -yl
Methyl radical

Double bond R: ? -ylidene Methylidene

Triple bond R⫶ ? -ylidyne Methylidyne

Carboxylic acyl radical Acyl R−C(=O)• ? -oyl Acetyl