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Functional group

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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.[1][2] However, its relative reactivity can be modified by nearby functional groups.

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.

Contents

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.

Hydrocarbons

Functional groups that 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
Alkane Alkyl RH Image:Alkyl-(general)-skeletal.svg alkyl- -ane Image:Methane-2D-stereo.svg
Methane
Alkene Alkenyl R2C=CR2 Image:Alkene-(general)-skeletal.png alkenyl- -ene Image:Ethylene.svg
Ethylene
(Ethene)
Alkyne Alkynyl RC≡CR' Image:Alkyne-(general)-skeletal.png alkynyl- -yne Image:Acetylene-2D.png
Acetylene
(Ethyne)
Benzene derivative Phenyl RC6H5
RPh
Image:Phenyl-group.png phenyl- -benzene Image:Cumene-2D-skeletal.png
Cumene
(2-phenylpropane)
Toluene derivative Benzyl RCH2C6H5
RBn
Image:Benzyl-group.png benzyl- 1-(substituent)toluene Image:Benzyl-bromide-skeletal.svg
Benzyl bromide
(1-Bromotoluene)

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 Image:Halide-group.png halo- alkyl halide Image:Chloroethane-skeletal.png
Chloroethane
(Ethyl chloride)
fluoroalkane fluoro RF Image:Fluoro-group.png fluoro- alkyl fluoride Image:Fluoromethane-2D.png
Fluoromethane
(Methyl fluoride)
chloroalkane chloro RCl Image:Chloro-group.png chloro- alkyl chloride Chloromethane
Chloromethane
(Methyl chloride)
bromoalkane bromo RBr Image:Bromo-group.png bromo- alkyl bromide Image:Bromomethane-2D.png
Bromomethane
(Methyl bromide)
iodoalkane iodo RI Image:Iodo-group.png iodo- alkyl iodide Image:Iodomethane.svg
Iodomethane
(Methyl iodide)

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

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 methanol
Methanol
Ketone Carbonyl RCOR' Image:Ketone-skeletal.png keto-, oxo- -one Image:Butanone-structure-skeletal.png
Methyl ethyl ketone
(Butanone)
Aldehyde Aldehyde RCHO Image:Aldehyde-skeletal.png aldo- -al Image:Acetaldehyde-skeletal.svg
Acetaldehyde
(Ethanal)
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 Sodium acetate
Sodium acetate
(Sodium ethanoate)
Carboxylic acid Carboxyl RCOOH Image:Carboxylic-acid-skeletal.svg carboxy- -oic acid Image:Acetic-acid-2D-skeletal.png
Acetic acid
(Ethanoic acid)
Ether Ether ROR' Image:Ether-(general).png alkoxy- alkyl alkyl ether Diethyl ether
Diethyl ether
(Ethoxyethane)
Ester Ester RCOOR' Image:Ester-skeletal.png alkyl alkanoate Image:Ethyl butyrate.png
Ethyl butyrate
(Ethyl butanoate)
Hydroperoxide Hydroperoxy ROOH Image:Hydroperoxide-group-2D.png hydroperoxy- alkyl hydroperoxide Image:Methyl-ethyl-ketone-peroxide-2D-skeletal.png
Methyl ethyl ketone peroxide
Peroxide Peroxy ROOR Image:Peroxy-group.png peroxy- alkyl peroxide Image:DTBP.png
Di-tert-butyl peroxide

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
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
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
Imide Imide RC(=O)NC(=O)R' Imide imido- -imide
Azide Azide RN3 Image:Azide-2D.png azido- alkyl azide Image:Phenyl azide-chemical.png
Phenyl azide
(Azidobenzene)
Azo compound Azo
(Diimide)
RN2R' Image:Azo-group.png azo- -diazene Image:Methyl-orange-skeletal.png
Methyl orange
(p-dimethylamino-azobenzenesulfonic acid)
Cyanates Cyanate ROCN Image:Cyanate-group.png cyanato- alkyl cyanate
Isocyanide RNC Image:Isocyanide-2D.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
Nitrate Nitrate RONO2 Image:Nitrate-group-2D.png nitrooxy-, nitroxy-

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)
Nitrite Nitrosooxy RONO Image:Nitrite-group-2D.png nitrosooxy-

alkyl nitrite

Image:Amyl nitrite.svg
[Isoamyl nitrite]]
(3-methyl-1-nitrosooxybutane)
Nitro compound Nitro RNO2 Image:Nitro-group.png nitro-   Image:Nitromethane2.png
Nitromethane
Nitroso compound Nitroso RNO Image:Nitroso-compound-2D.png nitroso-   Image:Nitrosobenzene.png
Nitrosobenzene
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

Groups containing phosphorus and sulfur

Compounds that 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
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
Sulfide or thioether 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)
Thiocyanate Thiocyanate RSCN Image:Thiocyanate-group.png thiocyanato- alkyl thiocyanate
Disulfide Disulfide RSSR' Image:Organic disulfide.png alkyl alkyl disulfide Image:Diphenyl disulfide.png
Diphenyl disulfide
1,2-diphenyldisulfane

Other

References

  1. ^ Compendium of Chemical Terminology (IUPAC "Gold Book") http://goldbook.iupac.org/F02555.html
  2. ^ March, Jerry (1985). Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third Edition, John Wiley & Sons. ISBN 0-471-85472-7. 


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