Many important organic chemistry molecules contain oxygen or nitrogen.

It's a good idea to

memorize the names and structures of these functional groups, or at least bookmark the
page to consult as needed.
 

 
Hydrocarbons

Functional groups, called hydrocarbyls, that contain only carbon and hydrogen, but vary in the number and order of π bonds. Each one differs in
type (and scope) of reactivity.

Chemical class Group Formula Structural Formula Prefix Suffix Example

Alkane Alkyl RH 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
(2-phenylpropane)

RCH2C6H5
Toluene derivative Benzyl benzyl- 1-(substituent)toluene
RBn
Benzyl bromide
(1-Bromotoluene)

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.

[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- alkyl chloride

Chloromethane
(Methyl chloride)

bromoalkane bromo RBr bromo- alkyl bromide

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 oxygen (carbonyl groups) and the donating effects of sp2 hybridized oxygen (alcohol groups).

Chemical Structural
Group Formula Prefix Suffix Example
class 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 -al
or
oxo- (=O)
Ethanal
(Acetaldehyde)

carbonofluo
ridoyl-
carbonochlo
Acyl Haloform ridoyl- -oyl
RCOX
halide yl carbonobro halide
midoyl- Acetyl chloride
carbonoiodi (Ethanoyl
doyl- chloride)

alkyl
Carbonat Carbonat (alkoxycarbo
ROCOOR carbonat Triphosgene
e e ester nyl)oxy-
e (Di(trichlorom
ethyl)
carbonate)

Carboxyla Carboxyla
RCOO− carboxy- -oate Sodium
te te
acetate
(Sodium
ethanoate)

Carboxyli
Carboxyl RCOOH carboxy- -oic acid
c acid

Acetic acid
(Ethanoic acid)

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

Hydroper Hydroper ROOH hydroperoxy alkyl

oxide oxy - hydroper
oxide
Methyl ethyl
ketone
 peroxide

alkyl
Peroxide Peroxy ROOR peroxy-
peroxide
Di-tert-butyl
peroxide

alkyl
Ether Ether ROR' alkoxy- Diethyl ether
ether
(Ethoxyethane
)

-al alkyl
Hemiacet Hemiacet RCH(OR')
alkoxy -ol hemiacet
al al (OH)
al

-one alkyl
Hemiketa RCH(ORʺ)
Hemiketal alkoxy -ol hemiketa
l (OH)R'
l

RCH(OR') -al dialkyl

Acetal Acetal dialkoxy-
(OR") acetal

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

Orthoeste Orthoest RC(OR')(ORʺ)

trialkoxy-
r er (OR‴)

Orthocar Orthocar tetraalkyl

C(OR)(OR')
bonate bonate tetralkoxy- orthocar
(ORʺ)(OR″)
ester ester bonate

[edit] Groups 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

carboxamido-
Amide Carboxamide RCONR2 or -amide
carbamoyl-
Acetamide
(Ethanamide)
 Primary amine RNH2 amino- -amine

Methylamine
(Methanamine)

Secondary
R2NH amino- -amine
amine
Dimethylamine
Amines

Tertiary amine R3N amino- -amine

Trimethylamine

4° ammonium
R4N+ ammonio- -ammonium
ion
Choline

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

Secondary
RC(=NR)R' imino- -imine
ketimine

Imine

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

Secondary
RC(=NR')H imino- -imine
aldimine
 Imide Imide RC(=O)NC(=O)R' imido- -imide

Azide Azide RN3 azido- alkyl azide

Phenyl azide
(Azidobenzene)

Azo
Azo compound RN2R' azo- -diazene
(Diimide) Methyl orange
(p-dimethylamino
azobenzenesulfonic

Cyanate ROCN cyanato- alkyl cyanate

Methyl cyanate
Cyanates

Isocyanate RNCO isocyanato- alkyl isocyanate

Methyl isocyanat

nitrooxy-,
Nitrate Nitrate RONO2 alkyl nitrate
nitroxy-
Amyl nitrate
(1-nitrooxypentan

Nitrile

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

Isonitrile RNC isocyano- alkaneisonitrile

alkyl isocyanide
 Methyl isocyanid

Nitrite Nitrosooxy RONO nitrosooxy- alkyl nitrite

Isoamyl nitrite
(3-methyl-1-nitrosooxyb

Nitro
Nitro RNO2 nitro-  
compound
Nitromethane

Nitroso
Nitroso RNO nitroso-  
compound
Nitrosobenzene

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

[edit] 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.

Chemical class Group Formula Structural Formula Prefix Suffix

sulfanyl-
Thiol Sulfhydryl RSH -thiol
(-SH)

Sulfide Sulfide RSR' substituent sulfanyl- di(substituent) sulfide

(Thioether) (-SR')
 (Methyls
Dim

substituent disulfanyl-
Disulfide Disulfide RSSR' di(substituent) disulfide
(-SSR')
(Methyldi
Dim

-sulfinyl-
Sulfoxide Sulfinyl RSOR' di(substituent) sulfoxide
(-SOR')
(Methane
Dim

-sulfonyl-
Sulfone Sulfonyl RSO2R' di(substituent) sulfone
(-SO2R')
(Methane
Dim

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

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

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

isothiocyanato-
Isothiocyanate RNCS substituent isothiocyanate
(-NCS)
A

Thione Carbonothioyl RCSR' -thioyl- -thione

(-CSR')
or
sulfanylidene-
 Dip
(=S)
(T

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

[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 Structural
Group Formula Prefix Suffix E
class Formula

Phosphine Phosphin
R3P phosphanyl- -phosphane
(Phosphane) o
Methylpr

Phosphonic Phosphon substituent

RP(=O)(OH)2 phosphono-
acid o phosphonic acid
Benzylph

phosphonooxy- Glyceraldehyde
Phosphat ROP(=O) substituent
Phosphate or
e (OH)2 phosphate
O-phosphono- (phospho-)
O-Phospho
(Phos

di(substituent)
[(alkoxy)hydroxyphosphoryl]o hydrogen phospha
xy- te
Phosphodiest Phosphat O-[(2-Guanidinoethoxy)h
HOPO(OR)2 or or
er e
O- phosphoric acid
[(alkoxy)hydroxyphosphoryl]- di(substituent) est (Lo
er

[edit]