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Functional group

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In organic chemistry, functional groups are specific groups of atoms 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.

The following is a list of common functional groups. In the formulas, the symbols R and R' usually denotes an attached hydrogen, or a hydrocarbon side chain of any length, but may sometimes refer to any group of atoms. Below is an image of multiple functional groups found in organic chemistry.

(For convenience, the basic functional groups covered in General Biology are also listed here)

Chemical class Group Formula Structural Formula Prefix Suffix Example
Acyl halide Haloformyl RCOX Image:Acyl-halide-skeletal.png haloformyl- -oyl halide Image:Acetyl-chloride.png
Acetyl chloride
(Ethanoyl chloride)
Alcohol Hydroxyl ROH Image:Alcohol-(general)-skeletal.png hydroxy- -ol Image:Methanol-2D.png
Methanol
Aldehyde Aldehyde RCHO Image:Aldehyde-skeletal.png oxo- -al Image:Acetaldehyde-skeletal.png
Acetaldehyde
(Ethanal)
Alkane Alkyl RH Image:Alkyl-(general)-skeletal.png alkyl- -ane Image:Methane-2D-stereo.png
Methane
Alkene Alkenyl R2C=CR2 Image:Alkene-(general)-skeletal.png alkenyl- -ene Image:Ethylene-2D.png
Ethylene
(Ethene)
Alkyne Alkynyl RC≡CR' Image:Alkyne-(general)-skeletal.png alkynyl- -yne Image:Acetylene-2D.png
Acetylene
(Ethyne)
Amide Carboxamide RCONR2 Image:Amide-(tertiary)-skeletal.png carboxamido- -amide Image:Acetamide structure.png
Acetamide
(Ethanamide)
Amines Primary amine RNH2 Image:1°-amino-group.png amino- -amine Image:Methylamine-2D.png
Methylamine
(Methanamine)
Secondary amine R2NH Image:Amine-(secondary).png amino- -amine Image:Dimethylamine-2D.png
Dimethylamine
Tertiary amine R3N Image:Amine-(tertiary).png amino- -amine trimethylamine
Trimethylamine
4° ammonium ion R4N+ Image:Quaternary-ammonium-cation.svg ammonio- -ammonium Image:Choline-skeletal.png
Choline
Azo compound Azo
(Diimide)
RN2R' Image:Azo-group.png azo- -diazene Image:Methyl-orange-skeletal.png
Methyl orange
(p-dimethylamino-azobenzenesulfonic acid)
Toluene derivative Benzyl RCH2C6H5
RBn
Image:Benzyl-group.png benzyl- 1-(substituent)toluene Image:Benzyl-bromide-skeletal.svg
Benzyl bromide
(1-Bromotoluene)
Carbonate Carbonate ester ROCOOR Image:Carbonate-group.png alkyl carbonate
Carboxylate Carboxylate RCOO Image:Carboxylate-resonance-hybrid.png

Image:Carboxylate-canonical-forms.png

carboxy- -oate Image:Sodium-acetate-2D-skeletal.png
Sodium acetate
(Sodium ethanoate)
Carboxylic acid Carboxyl RCOOH Image:Carboxylic-acid-skeletal.png carboxy- -oic acid Image:Acetic-acid-2D-skeletal.png
Acetic acid
(Ethanoic acid)
Cyanates Cyanate ROCN Image:Cyanate-group.png cyanato- alkyl cyanate
Thiocyanate RSCN Image:Thiocyanate-group.png thiocyanato- alkyl thiocyanate
Ether Ether ROR' Image:Ether-(general).png alkoxy- alkyl alkyl ether Image:Diethyl-ether-2D-skeletal.png
Diethyl ether
(Ethoxyethane)
Ester Ester RCOOR' Image:Ester-skeletal.png -oate Image:Ethyl butyrate.png
Ethyl butyrate
(Ethyl butanoate)
Haloalkane Halo RX Image:Halide-group.png halo- alkyl halide Image:Chloroethane-skeletal.png
Chloroethane
(Ethyl chloride)
Hydroperoxide Hydroperoxy ROOH Image:Hydroperoxide-group-2D.png hydroperoxy- alkyl hydroperoxide Image:Methyl-ethyl-ketone-peroxide-2D-skeletal.png
Methyl ethyl ketone peroxide
Imine Primary ketimine RC(=NH)R' Image:Imine-(primary)-skeletal.png imino- -imine
Secondary ketimine RC(=NR)R' Image:Imine-(secondary)-skeletal.png imino- -imine
Primary aldimine RC(=NH)H Image:Aldimine-(primary)-skeletal.png imino- -imine
Secondary aldimine RC(=NR')H Image:Aldimine-(secondary)-skeletal.png imino- -imine
Isocyanide Isocyanide RNC Image:Isocyanide.png isocyano- alkyl isocyanide
Isocyanates Isocyanate RNCO Image:Isocyanate-group.png isocyanato- alkyl isocyanate Image:Methyl-isocyanate.png
Methyl isocyanate
Isothiocyanate RNCS Image:Isothiocyanate-group.png isothiocyanato- alkyl isothiocyanate Image:Allyl-isothiocyanate-2D-skeletal.png
Allyl isothiocyanate
Ketone Ketone RCOR' Image:Ketone-skeletal.png keto-, oxo- -one Image:Butanone-structure-skeletal.png
Methyl ethyl ketone
(Butanone)
Nitrate Nitrate RONO2 Image:Nitrate-group-2D.png nitrooxy-

alkyl nitrate

Image:Amyl-nitrate-2D-skeletal.png
Amyl nitrate
(1-nitrooxypentane)
Nitrile Nitrile RCN Image:Nitrile-(general)-skeletal.png cyano-

alkanenitrile
alkyl cyanide

Image:Benzonitrile structure.png
Benzonitrile
(Phenyl cyanide)
Nitro compound Nitro RNO2 Image:Nitro-group.png nitro-   Image:Nitromethane2.png
Nitromethane
Nitroso compound Nitroso RNO Image:Nitroso-group.png nitroso-   Image:Nitrosobenzene.png
Nitrosobenzene
Peroxide Peroxy ROOR Image:Peroxy-group.png peroxy- alkyl peroxide Image:DTBP.png
Di-tert-butyl peroxide
Benzene derivative Phenyl RC6H5 Image:Phenyl-group.png phenyl- -benzene Image:Cumene-2D-skeletal.png
Cumene
(2-phenylpropane)
Phosphine Phosphino R3P Image:Phosphine-general.svg phosphino- -phosphane Image:Methylpropylphosphane-skeletal.svg
Methylpropylphosphane
Phosphodiester Phosphate HOPO(OR)2 Image:Phosphodiester-group.png phosphoric acid di(substituent) ester di(substituent) hydrogenphosphate DNA
Phosphonic acid Phosphono RP(=O)(OH)2 Image:Phosphonic-acid-generic.png phosphono- substituent phosphonic acid Image:Benzylphosphonic-acid-2D-skeletal.png
Benzylphosphonic acid
Phosphate Phosphate ROP(=O)(OH)2 Image:Phosphate-group.png phospho- Image:G3P-2D-skeletal.png
Glyceraldehyde 3-phosphate
Pyridine derivative Pyridyl RC5H4N

Image:4-pyridyl.png
Image:3-pyridyl.png
Image:2-pyridyl.png

4-pyridyl
(pyridin-4-yl)

3-pyridyl
(pyridin-3-yl)

2-pyridyl
(pyridin-2-yl)

-pyridine Image:Nicotine-2D-skeletal.png
Nicotine
Sulfide RSR' Image:Sulfide-group-2D.png di(substituent) sulfide Image:Dimethylsulfide.png
Dimethyl sulfide
Sulfone Sulfonyl RSO2R' Image:Sulfone.png sulfonyl- di(substituent) sulfone Image:Dimethylsulfone Structure.png
Dimethyl sulfone
(Methylsulfonylmethane)
Sulfonic acid Sulfo RSO3H Image:Sulfonic-acid.png sulfo- substituent sulfonic acid Image:Benzenesulfonic-acid-2D-skeletal.png
Benzenesulfonic acid
Sulfoxide Sulfinyl RSOR' Image:Sulfoxide.png sulfinyl- di(substituent) sulfoxide Image:Diphenyl-sulfoxide.png
Diphenyl sulfoxide
Thiol Sulfhydryl RSH Image:Thiol-group.png mercapto-, sulfanyl- -thiol Image:Ethanethiol-skeletal.png
Ethanethiol
(Ethyl mercaptan)

Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming organic compounds.

The non-hydrogen atoms of functional groups are always associated with each other and with the rest of the molecule by covalent bonds. When the group of atoms is associated with the rest of the molecule primarily by ionic forces, the group is referred to more properly as a polyatomic ion or complex ion. And all of these are called radicals, by a meaning of the term radical that predates the free radical.

The first carbon after the carbon that attaches to the functional group is called the alpha carbon.

Functional groups are attached to the carbon backbone of organic molecules. They determine the characteristics and chemical reactivity of molecules. Functional groups are far less stable than the carbon backbone and are likely to participate in chemical reactions. Six common biological functional groups are hydrogen, hydroxyl, carboxyl, amino, phosphate, and methyl.

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Topics in organic chemistry

Aromaticity | Covalent bonding | Functional groups | Nomenclature | Organic compounds | Organic reactions | Organic synthesis | Publications | Spectroscopy | Stereochemistry

List of organic compounds
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