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 side chain of any length, but may sometimes refer to any group of atoms. [edit]Hydrocarbons Functional groups, called hydrocarbyls, that contain only carbon and hydrogen, but vary in the number and order of bonds. Each one differs in type (and scope) of reactivity.

Chemica Group Formula l class

Structural Formula

Prefix

Suffix

Example

Alkane

Alkyl

RH

alkyl-

-ane Ethane

Alkene

Alkeny R2C=CR2 l

alkenyl -

-ene Ethylene (Ethene)

Alkyne

Alkyny l

RCCR'

alkynyl -

-yne

Acetylene (Ethyne)

Benzene Phenyl derivative

RC6H5 RPh

phenyl-

-benzene

Cumene (2phenylpropane)

Toluene Benzyl derivative

RCH2C6H
5

RBn

1benzyl- (substituent)toluen Benzyl bromide e (Bromotoluene)

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

containing halogens

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 class

Group Formula

Structural Formula

Prefix

Suffix

Example

haloalkane

halo

RX

halo-

alkyl halide

Chloroethane (Ethyl chloride)

fluoroalkane

fluoro

RF

fluoro- alkyl fluoride Fluoromethane (Methyl fluoride)

chloroalkane

chloro

RCl

chloro- alkylchloride

Chloromethane

(Methyl chloride)

bromoalkane

bromo

RBr

bromo- alkylbromide Bromomethane (Methyl bromide)

iodoalkane

iodo

RI

iodo-

alkyl iodide Iodomethane (Methyl iodide)

[edit]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 2 oxygen (carbonyl groups) and the donating effects of sp hybridized oxygen (alcohol groups).

Chemical class

Group

Formula

Structural Formula

Prefix

Suffix

Example

Alcohol

Hydroxyl

ROH

hydroxy-

-ol Methanol

Ketone

Carbonyl

RCOR'

-oyl- (-COR') or oxo- (=O)

-one Butanone (Methyl ethyl ketone)

Aldehyde

Aldehyde

RCHO

formyl- (COH) or oxo- (=O)

-al Ethanal (Acetaldehyde)

Acyl halide

Haloformyl

RCOX

carbonofluorid oylcarbonochlori doyloyl hali carbonobromi de doylcarbonoiodido yl-

Acetyl chloride (Ethanoyl chloride)

Carbonate

Carbonate ester

ROCOOR

alkyl ca (alkoxycarbon rbonat yl)oxye

Triphosgene (Di(trichloromethyl) carbonate)

Carboxylate

Carboxylate

RCOO

carboxy-

-oate Sodium acetate (Sodium ethanoate)

Carboxylic acid

Carboxyl

RCOOH

carboxy-

oic acid Acetic acid (Ethanoic acid)

Ester

Ester

RCOOR'

alkanoyloxyalkyl or alkanoa alkoxycarbony te l alkylhy droper oxide

Ethyl butyrate (Ethyl butanoate)

Hydroperoxide

Hydroperoxy

ROOH

hydroperoxy-

Methyl ethyl ketone peroxide

Peroxide

Peroxy

ROOR

peroxy-

alkyl pe roxide

Di-tert-butyl peroxide

Ether

Ether

ROR'

alkoxy-

alkyl et her -al alkylhe miacet al -one alkylhe miketal -al dialkyla cetal -one dialkylk etal

Diethyl ether (Ethoxyethane)

Hemiacetal

Hemiacetal

RCH(OR')(OH)

alkoxy -ol

Hemiketal

Hemiketal

RC(OR)(OH)R'

alkoxy -ol

Acetal

Acetal

RCH(OR')(OR")

dialkoxy-

Ketal (orAcetal) Ketal (orAcetal)

RC(OR)(OR)R'

dialkoxy-

Orthoester

Orthoester

RC(OR')(OR)(OR)

trialkoxytetraalk ylortho carbon ate

Orthocarbonate Orthocarbonate C(OR)(OR')(OR)(OR) ester ester [edit]Groups

tetralkoxy-

containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.

Chemical class

Group

Formula

Structural Formula

Prefix

Suffix

Example

Amide

Carboxamide

RCONR2

carboxamidoor carbamoyl-

-amide Acetamide (Ethanamide)

Primary amine

RNH2

amino-

-amine Methylamine (Methanamine)

Secondary amine

R2NH

amino-

-amine Dimethylamine

Amines

Tertiary amine

R3N

amino-

-amine Trimethylamine

4 ammonium ion

R4N

ammonio-

-ammonium Choline

Primary ketimine

RC(=NH)R'

imino-

-imine

Imine

Secondary ketimine

RC(=NR)R'

imino-

-imine

Primary aldimine

RC(=NH)H

imino-

-imine

Secondary aldimine

RC(=NR')H

imino-

-imine

Imide

Imide

(RCO)2NR'

imido-

-imide

Azide

Azide

RN3

azido-

alkyl azide

Phenyl azide (Azidobenzene)

Azo compound

Azo (Diimide)

RN2R'

azo-

-diazene

Methyl orange (p-dimethylaminoazobenzenesulfonic acid)

Cyanate

ROCN

cyanato-

alkyl cyanate Methyl cyanate

Cyanates

Isocyanate

RNCO

isocyanato-

alkyl isocyanate Methyl isocyanate

Nitrate

Nitrate

RONO2

nitrooxy-, nitroxy-

alkyl nitrate Amyl nitrate

(1-nitrooxypentane)

Nitrile Nitrile

RCN

cyano-

alkanenitrile alkyl cyanide

Benzonitrile (Phenyl cyanide)

Isonitrile

RNC

isocyano-

alkaneisonitrile alkyl isocyanide

Methyl isocyanide

Nitrite

Nitrosooxy

RONO

nitrosooxy-

alkyl nitrite

Isoamyl nitrite (3-methyl-1nitrosooxybutane)

Nitro compound

Nitro

RNO2

nitroNitromethane

Nitroso compound

Nitroso

RNO

nitrosoNitrosobenzene 4-pyridyl (pyridin-4-yl)

Pyridine derivative

Pyridyl

RC5H4N

3-pyridyl (pyridin-3-yl)

-pyridine Nicotine

2-pyridyl (pyridin-2-yl) [edit]Groups

containing sulphur

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 class

Group

Formula

Structural Formula

Prefix

Suffix

Example

Thiol

Sulfhydryl

RSH

sulfanyl(-SH)

-thiol Ethanethiol

Sulfide (Thioether)

Sulfide

RSR'

substituent sulfanyl di(substitu ent) sulfid e (-SR')

(Methylsulfanyl)methane (prefix) or Dimethyl sulfide (suffix)

Disulfide

Disulfide

RSSR'

substituent disulfa di(substitu ent) disulf nyl(Methyldisulfanyl)methane (prefix) ide (-SSR') or Dimethyl disulfide (suffix)

Sulfoxide

Sulfinyl

RSOR'

-sulfinyl(-SOR')

di(substitu ent) sulfo xide (Methanesulfinyl)methane (prefix) or Dimethyl sulfoxide (suffix)

Sulfone

Sulfonyl

RSO2R'

-sulfonyl(-SO2R')

di(substitu ent) sulfo (Methanesulfonyl)methane (prefix) ne or Dimethyl sulfone (suffix)

Sulfinic aci d

Sulfino

RSO2H

sulfino(-SO2H)

sulfinic ac id

2-Aminoethanesulfinic acid

Sulfonic aci d

Sulfo

RSO3H

sulfo(-SO3H)

sulfonic a cid

Benzenesulfonic acid

Thiocyanat e Thiocyanat e Isothiocya nate

RSCN

thiocyanato(-SCN)

substituent thiocyan ate

Phenyl thiocyanate

RNCS

isothiocyanato(-NCS)

substituent isothiocy anate

Allyl isothiocyanate

Thione

Carbonothi oyl

RCSR'

-thioyl(-CSR') or sulfanylidene(=S)

-thione Diphenylmethanethione (Thiobenzophenone)

Thial

Carbonothi oyl

RCSH

methanethioyl(-CSH) or sulfanylidene(=S)

-thial

[edit]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.

Chemical class

Group

Formula

Structural Formula

Prefix

Suffix

Example

Phosphine (Phosphane)

Phosphin o

R3P

phosphanyl -

-phosphane

Methylpropylphosph ane

Phosphonic acid

Phospho no

RP(=O)(OH)2

phosphono-

substituentphosphoni c acid

Benzylphosphonic acid

Phosphate

Phosphat ROP(=O)(OH) e 2

phosphono oxyor substituentphosphate Ophosphono(phospho-)

Glyceraldehyde 3phosphate (suffix)

OPhosphonocholine (p refix) (Phosphocholine)

[(alkoxy)hydrox yphosphoryl]ox

DNA di(substituent) hydrogen phosphate or phosphoric acid di(substituent) ester

Phosphodiester

Phosphat e

y-

HOPO(OR)2

or O[(alkoxy)hydrox yphosphoryl]-

O-[(2-Guanidinoethoxy)hydr oxyphosphoryl]-L-serine

(p

refix) (Lombricine)

[edit]See

also