Functional group

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

## Contents

* 1 Overview
* 2 Table of common functional groups
* 2.1 Hydrocarbons
* 2.2 Groups containing halogens
* 2.3 Groups containing oxygen
* 2.4 Groups containing nitrogen
* 2.5 Groups containing phosphorus and sulfur
* 2.6 Other
* 2.7 See also
* 2.8 External links

## Overview

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In organic chemistry, functional groups (or moieties) 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.

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 atom 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.

# Table of common functional groups

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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.

## Hydrocarbons

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Functional groups which vary based upon the number and order of π bonds impart different chemistry. Each listing below contains C-H bonds, but each one differs in type (and scope) of reactivity.

Chemical class | Group  | Formula  | Structural Formula  | Prefix  | Suffix  | Example

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Alkane | Alkyl | RH  |  | alkyl- | -ane  |
Ethane
Alkene | Alkenyl | R2C=CR2 |  | alkenyl- | -ene  |
Ethylene
(Ethene)
Alkyne | Alkynyl | RC≡CR'  |  | alkynyl- | -yne  |
Acetylene
(Ethyne)
Benzene derivative | Phenyl | RC6H5 |  | phenyl- | -benzene  |
Cumene
(2-phenylpropane)
Toluene derivative | Benzyl | RCH2C6H5
RBn  |  | benzyl-  | 1-(substituent)toluene  |
Benzyl bromide
(1-Bromotoluene)

## Groups containing halogens

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Haloalkanes are a class of molecule which 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

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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

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Compounds which 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 sp2 hybridized oxygen and the donating effects of sp3 hybridized oxygen.

Chemical class | Group  | Formula  | Structural Formula  | Prefix  | Suffix  | Example

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Acyl halide | Haloformyl  | RCOX  |  | haloformyl- | -oyl halide  |
Acetyl chloride
(Ethanoyl chloride)
Alcohol | Hydroxyl | ROH  |  | hydroxy- | -ol  |
Methanol
Ketone | Carbonyl | RCOR'  |  | keto-, oxo- | -one  |
Methyl ethyl ketone
(Butanone)
Aldehyde | Aldehyde | RCHO  |  | aldo- | -al  |
Acetaldehyde
(Ethanal)
Carbonate | Carbonate ester | ROCOOR  |  |  | alkyl carbonate |
Carboxylate | Carboxylate | RCOO− |

| carboxy- | -oate  |
Sodium acetate
(Sodium ethanoate)
Carboxylic acid | Carboxyl | RCOOH  |  | carboxy- | -oic acid  |
Acetic acid
(Ethanoic acid)
Ether | Ether | ROR'  |  | alkoxy-  | alkyl alkyl ether |
Diethyl ether
(Ethoxyethane)
Ester | Ester | RCOOR'  |  |  | alkyl alkanoate |
Ethyl butyrate
(Ethyl butanoate)
Hydroperoxide | Hydroperoxy | ROOH  |  | hydroperoxy-  | alkyl hydroperoxide |
Methyl ethyl ketone peroxide
Peroxide | Peroxy | ROOR  |  | peroxy-  | alkyl peroxide |
Di-tert-butyl peroxide

## Groups containing nitrogen

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Compounds which 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

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Amide | Carboxamide | RCONR2 |  | carboxamido- | -amide  |
Acetamide
(Ethanamide)
Amines | Primary amine | RNH2 |  | amino- | -amine  |
Methylamine
(Methanamine)
Secondary amine | R2NH  |  | amino- | -amine  |
Dimethylamine
Tertiary amine | R3N  |  | amino- | -amine  |
Trimethylamine
4° ammonium ion | R4N+ |  | ammonio- | -ammonium  |
Choline
Imine | Primary ketimine | RC(=NH)R'  |  | imino- | -imine  |
Secondary ketimine | RC(=NR)R' |  | imino- | -imine  |
Primary aldimine | RC(=NH)H  |  | imino- | -imine  |
Secondary aldimine | RC(=NR')H  |  | imino- | -imine  |
Imide | Imide | RC(=O)NC(=O)R'  |  | imido-  | -imide
Azide | Azide | RN3 |  | azido- | alkyl azide |
Phenyl azide
(Azidobenzene)
Azo compound | Azo
(Diimide) | RN2R'  |  | azo- | -diazene  |
Methyl orange
(p-dimethylamino-azobenzenesulfonic acid)
Cyanates | Cyanate | ROCN  |  | cyanato-  | alkyl cyanate |
Isocyanide | RNC  |  | isocyano-  | alkyl isocyanide |
Isocyanates | Isocyanate | RNCO  |  | isocyanato-  | alkyl isocyanate |
Methyl isocyanate
Isothiocyanate | RNCS  |  | isothiocyanato-  | alkyl isothiocyanate |
Allyl isothiocyanate
Nitrate | Nitrate | RONO2 |  | nitrooxy-, nitroxy- |

alkyl nitrate

Amyl nitrate
(1-nitrooxypentane)
Nitrile | Nitrile | RCN  |  | cyano- |

alkanenitrile
alkyl cyanide

Benzonitrile
(Phenyl cyanide)
Nitrite | Nitrosooxy | RONO  |  | nitrosooxy- |

alkyl nitrite

Amyl nitrite
(3-methyl-1-nitrosooxybutane)
Nitro compound | Nitro | RNO2 |  | nitro- |  |
Nitromethane
Nitroso compound | Nitroso | RNO  |  | nitroso- |  |
Nitrosobenzene
Pyridine derivative | Pyridyl | RC5H4N  |

4-pyridyl
(pyridin-4-yl)

3-pyridyl
(pyridin-3-yl)

2-pyridyl
(pyridin-2-yl)

| -pyridine  |
Nicotine

## Groups containing phosphorus and sulfur

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

Chemical class | Group  | Formula  | Structural Formula  | Prefix  | Suffix  | Example

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Phosphine | Phosphino  | R3P  |  | phosphino- | -phosphane  |
Methylpropylphosphane
Phosphodiester | Phosphate | HOPO(OR)2 |  | phosphoric acid di(substituent) ester  | di(substituent) hydrogenphosphate  | DNA
Phosphonic acid | Phosphono  | RP(=O)(OH)2 |  | phosphono-  | substituent phosphonic acid  |
Benzylphosphonic acid
Phosphate | Phosphate  | ROP(=O)(OH)2 |  | phospho- |  |
Glyceraldehyde 3-phosphate
Sulfide or thioether |  | RSR'  |  |  | di(substituent) sulfide  |
Dimethyl sulfide
Sulfone | Sulfonyl | RSO2R'  |  | sulfonyl-  | di(substituent) sulfone  |
Dimethyl sulfone
(Methylsulfonylmethane)
Sulfonic acid | Sulfo  | RSO3H  |  | sulfo-  | substituent sulfonic acid |
Benzenesulfonic acid
Sulfoxide | Sulfinyl | RSOR'  |  | sulfinyl-  | di(substituent) sulfoxide |
Diphenyl sulfoxide
Thiol | Sulfhydryl | RSH  |  | mercapto-, sulfanyl-  | -thiol  |
Ethanethiol
(Ethyl mercaptan)
Thiocyanate | Thiocyanate | RSCN  |  | thiocyanato-  | alkyl thiocyanate |
Disulfide | Disulfide | RSSR'  |  |  | alkyl alkyl disulfide  |
Diphenyl disulfide
1,2-diphenyldisulfane

## Other

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* Methyl
* Methylene
* Ethyl
* Propyl
* Butyl
* Hydroxy
* Methoxy
* Hydroxymethyl
* Methylenedioxy
* Phenyl
* Acetyl
* Acetoxy
* Thioamide
* Thioester
* Thioketone

## See also

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* Compendium of Chemical Terminology (IUPAC "Gold Book")

## External links

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* IUPAC Blue Book (organic nomenclature)
* IUPAC ligand abbreviations (pdf)

Template:Functional Groups Template:Organic chemistry

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