Functional group

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In chemistry, a functional group is a chain or group attached to a carbon chain, represented in the general formula by R for aliphatic compounds and as Ar for aromatic compounds, and which are responsible for the reactivity and chemical properties of organic compounds. They are always associated with covalent bonds to the rest of the molecule.

The chemical nomenclature of organic compounds is based on the combination of the prefixes (secondary function) and suffixes (main function) associated with the functional groups together with the names of the alkanes from which they are derived by accessing the atoms.

Homologous series and most common functional groups

A homologous series is a set of compounds that share the same functional group and therefore have similar properties and reactions. For example: the homologous series of primary alcohols possess an OH (hydroxyl) group on a terminal or primary carbon.

The homologous series and functional groups listed below are the most common. In the tables, the symbols R, R', or the like, can refer to a hydrocarbon chain, a hydrogen atom, or even any set of atoms.

Saturated

  • Alkanes

Unsaturated

  • Alkenes (methine functional group)
  • Alkynes (alkynyl functional group)

Oxygen functions

Presence of some carbon-oxygen bond: single (CO) or double (C=O)

Functional groupHomologous seriesFormulaStructurePrefixSuffixExample
hydroxyl groupAlcoholR-OHhydroxy--olEthanol (Ethyl Alcohol)Ethanol
Alkoxy (or aryloxy) groupEtherROR'alkoxy-oxy-R -yl R' -yl etherEthoxyethane or Diethyl Ether (Ethyl Ether)Ethyl ether
carbonyl groupAldehydeRC(=O)Hcarbonylformil--to the-carbaldehydeEthanal (acetaldehyde)Ethanal
KetoneRC(=O)-R'carbonyloxo--onepropanone (acetone)propanone
carboxyl groupCarboxylic acidR-COOHcarboxylcarboxy--ic acidEthanoic acid (acetic acid)Acetic acid
acyl groupEsterR-COO-R'acyl-yloxycarbonyl-R' - yl R - ateEthyl Ethanoate (Ethyl Acetate)Ethyl acetate

For the nomenclature of these functional groups, see Nomenclature of organic functions with oxygen.

Nitrogenous functions

Amides, amines, nitro compounds, Nitriles. Presence of carbon-nitrogen bonds: CN, C=N or C≡N

Functional groupcompound typeFormulaStructurePrefixSuffixExample
amino groupAmineR-NH 2Not meNot me--Not meIsobutylamine.svgIsobutylamine
imineRNCH 2imine__1,5-Diazabicyclo[4.3.0]non-5-ene (BDN)
aminoand carbonyl groupsAmideR-CO-NR 2amide_-amideacetamideacetamide
imideRC(=O)N(-R')-R"imide__Tetraacetylethylenediamine.pngTetramethylethyldiimide
nitro groupnitro compoundR-NO 2nitronitro-_2-Nitropropane.svgnitropropane
nitrile groupnitrile or cyanideR-CNNitrile or Cyanidecyano--nitrileTetracyanoethylene (TCNE)
isocyanideR-NCisocyanidealkyl isocyanide_Tert-butylisocyanide.pngTert-butyl isocyanide
isocyanateR-NCOisocyanatealkyl isocyanate_methyl isocyanate
isothiocyanateR-NCSisothiocyanatealkyl isothiocyanateallyl isothiocyanate
azo groupazo derivativeRN=NR'azoazo--diazeneDiethyl azodicarboxylate (DEAD)
Diazo derivativeR=N=NDiazo derivativediazo-_Diazomethane.svgDiazomethane
azideRN 3azide ionazido--azide2-Dimethylaminoethylazide (DMAZ)
diazonium saltXRN ≡N _diazonium salt_...ide of...-diazoniumBenzenediazonium cation
_hydrazineR 1 R 2 N-NR 3 R 4Hydrazines_-hydrazineHydrazide (general formula)
_hydroxylamine-NOHhydroxylamines_-hydroxylamineN,N-dimethylhydroxylamine

Halogenated functions

Composed of carbon, hydrogen and halogens.

Functional groupcompound typecompound formulaPrefix
halide grouphalideRXhalo-_
acyl groupacid halideR-COXHaloformil--oil halide

Sulfur-containing groups

Functional groupcompound typecompound formulaPrefixSuffix
sulfide groupthioether or sulfideRSR'alkylthio-
R-SHthiolmercapto--thiol
R-SO-R'Sulfoxide___
R-SO 2 -R'Sulfone___
_sulfonic acidRSO 3H _sulfo--sulfonic acid

Organophosphates

Functional groupcompound typeFormulaStructurePrefixSuffixExample
sodium phosphinatePR 3phosphine__
P(=O) R3phosphine oxide__Hexamethylphosphoramide (HMPA)
phosphiniteP(OR)R 2phosphinite__
phosphinateP(=O)(OR)R 2phosphinate__chloroethylphosphinate
phosphoniteP (OR) 2Rphosphonite__HEDP
PhosphonateP(=O)(OR) 2 RPhosphonate__N-phosphonomethyl glycine(Glyphosate)
PhosphiteQ(OR) 3Phosphite.png_phosphitetrimethyl phosphite
Phosphate groupPhosphateP(=O)(OH) 2RPhosphate__triethyl phosphate
phosphoranePR 5phosphorane__dichlorotriphenylphosphine

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