Functional Groups A - Chemistry LibreTexts

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  1. Carbon based
  2. Oxygen based
  3. Nitrogen based
  4. Sulfur based
  5. Contributors

In organic chemistry, functional groups are specific groups of atoms within molecules arranged in a specific manner. The following tables list common functional groups arranged by heteroatom. The symbols R, R', R'' and R''' usually denote a hydrocarbon chain or a hydrogen but can sometimes be any group of atoms. The symbol X denotes a halide such as F, Br, Cl or I.

Carbon based

Chemical class Group Formula Structural Formula Prefix Suffix Example
Alkane Alkyl RH Alkane.png alkyl- -ane Butane.png Butane
Alkene Alkenyl R2C=CR2 Alkene.png alkenyl- -ene Butene.png (E)-But-2-ene
Alkyne Alkynyl RC≡CR' Alkyne.png alkynyl- -yne Butyne.png But-2-yne
Allene Allenyl R2C=C=CR2 Allene.png allenyl- -diene Pentadiene.png Penta-2,3-diene
Cumulene Cumulenyl R2C=C=C=CR2 Cumulene.png cumulenyl- -triene Hexa234triene.png Hexa-2,3,4-triene
Benzene derivative Phenyl RC6H5 RPh Phenyl.png phenyl- -benzene Propylbenzene.png Propylbenzene (Phenylpropane)
Toluene derivative Benzyl RCH2C6H5 RBn Benzyl.png benzyl- -toluene Benzylbromide.png Benzylbromide (α-bromotoluene)
Halide Halo RX Halide.png halo- -halide Butyliodide.png Butyl iodide (1-Iodobutane)

Oxygen based

Chemical class Group Formula Structural Formula Prefix Suffix Example
Ether Ether ROR' Ether.png alkoxy- -ether Diethylether.png Diethyl ether (Ethoxyethane)
Alcohol Hydroxyl ROH Alcohol.png hydroxy- -ol Butan-1-ol.png n-Butanol (Butan-1-ol)
Aldehyde Carbonyl RCHO Aldehyde.png aldo- -al Butyraldehyde.png Butyraldehyde (Butanal)
Ketone Carbonyl RCOR' Ketone.png keto- -one Butan-2-one.png 2-Butanone (Methyl ethyl ketone)
Carboxylic Acid Carboxyl RCO2H Carboxylic acid.png carboxy- -oic acid Butanoic acid.png Butanoic acid (Butyric acid)
Acyl halide Haloformyl RCOX Acyl halide.png haloformyl- -oyl halide Butanoyl bromide.png Butanoyl bromide (Butyryl bromide)
Ester Ester RCO2R' Ester.png / -(o)ate Ethyl acetate.png Ethyl acetate (Ethyl ethanoate)
Lactone Lactone / Lactone.png / -lactone Butyrolactone.png γ-Butyrolactone
Peroxy acid Peracid RCO3H Peroxyacid.png per- peroxy- -peroxoic acid Peracetic acid.png Peracetic acid Peroxyacetic acid (Ethaneperoxoic acid)
Anhydride Anhydride RCOOCOR' Anhydride.png -(o)ic anhydride Acetic anhydride.png Acetic anhydride (Ethanoic anhydride)
Carbonate Carbonate ROCOOR' Carbonate.png / -carbonate Dimethyl carbonate.png Dimethyl carbonate
Epoxide Epoxide/Oxirane / Epoxide.png epoxy- -oxirane / -ene oxide 2-methyloxirane.png 2-Methyloxirane 1,2-Epoxypropane 1,2-Propylene oxide
Hydrate Diol RC(OH)(OH)R' Hydrate.png / -diol Butane-22-diol.png Butane-2,2-diol
Hemiacetal Hemiacetal RCH(OR')(OH) Hemiacetal.png / / 1-methoxypropan-1-ol.png 1-Methoxypropan-1-ol
Acetal Acetal RCH(OR')(OR'') Acetal.png dialkoxy- -dialkyl acetal 11-dimethoxypropane.png 1,1-Dimethoxypropane Butyraldehyde dimethyl acetal
Hemiketal Hemiketal RC(OR'')(OH)R' Hemiketal.png / / 2-methoxybutan-2-ol.png 2-Methoxybutan-2-ol
Ketal Ketal RC(OR'')(OR''')R' Ketal.png dialkoxy- -dialkyl acetal 22-dimethoxybutane.png 2,2-Dimethoxybutane 2-Butanone dimethyl acetal
Orthoester Orthoester RC(OR')(OR'')(OR''') Orthoester.png trimethoxy- -orthoacetate Trimethylorthoacetate.png Trimethylorthoacetate (1,1,1-Trimethoxyethane)
Orthocarbonate Orthocarbonate ROC(OR')(OR'')(OR''') Orthocarbonate.png tetraalkoxy- -orthocarbonate Tetramethylorthocarbonate.png Tetramethylorthocarbonate (1,1,1,1-Tetramethoxymethane)
Phenol Phenol PhOH Phenol.png / -phenol M-cresol.png 3-Methylphenol m-Cresol
Enol Enol RC(OH)=CR'2 Enol.png / -enol But-2-en-2-ol.png But-2-en-2-ol
Enol ether Enol ether RC(OR')=CR''2 Enol ether.png / alkoxy -ene 2-methoxybut-2-ene.png 2-methoxybut-2-ene
Hydroperoxide Hydroperoxide ROOH Hydroperoxide.png hydroperoxy- -hydroperoxide 1-hydroperoxypropane.png 1-Hydroperoxypropane n-Propylhydroperoxide
Peroxide Peroxide ROOR' Peroxide.png peroxy- -peroxide Ditertbutyl peroxide.png Di-tert-butyl peroxide
Ketene Ketene RC(=C=O)R' Ketene.png / -ketene 2-methylbut-1-en-1-one.png Methyl ethyl ketene (2-Methylbut-1-en-1-one)

Nitrogen based

Chemical class Group Formula Structural Formula Prefix Suffix Example
Amine Amino RNH2 Amine.png amino- -amine Butan-1-amine.png Butan-1-amine 1-Aminobutane)
Aldimine / Imine RCHNH2 Aldimine.png Butan-1-imine.png Butan-1-imine
Ketimine / Imine Ketimine.png Butan-2-imine.png Butan-2-imine
Ketenimine Ketenimine.png 2-methylbut-1-en-1-imine.png 2-Methylbut-1-en-1-imine
Nitrile / Cyanide Nitrile.png Butyronitrile.png Butyronitrile 1-Cyanobutane
Isocyanide / Isonitrile Isonitrile.png 1-isocyanopropane.png 1-Isocyanopropane 1-Propylisocyanide
Azide Azide.png 1-azidopropane.png 1-Azidopropane 1-Propylazide
Azo compound / Diimide / Diazene Azo compound.png 1,2-diethyldiazene.png (E)-1,2-diethyldiazene (Azoethane)
Diazonium salt Diazonium salt.png Butane-2-diazonium.png Butane-2-diazonium (2-Diazobutane)
Carbodiimide Carbodiimide.png Diisopropylcarbodiimide.png N,N'-Diisopropylcarbodiimide
Amidine Amidine.png Propylamidine.png Propylamidine
Amidrazone Amidrazone.png Propylamidrazone.png Propylamidrazone (Propionimidohydrazide)
Guanidine Guanidine.png 1,3-diethyl-2-methylguanidine.png 1,3-Diethyl-2-methylguanidine
Hydrazine Hydrazine.png 1-ethyl-2-methylhydrazine.png 1-Ethyl-2-methylhydrazine
Hydrazone Hydrazone.png Acetone N,N-dimethylhydrazone.png Acetone N,N-dimethylhydrazone
Aminal Aminal.png Propane-2,2-diamine.png Propane-2,2-diamine
Hemiaminal Hemiaminal.png 2-aminopropan-2-ol.png 2-Aminopropan-2-ol
Enamine Enamine.png But-2-en-2-amine.png (Z)-But-2-en-2-amine
Aniline Aniline.png
Hydroxylamine Hydroxyl amine.png
Amine oxide / N-oxide N-oxide.png
Aldoxime Aldoxime.png Propionaldehyde oxime.png Propionaldehyde oxime
Ketoxime Ketoxime.png
Aldoxime ether Aldoxime ether.png Propionaldehyde O-methyl oxime.png Propionaldehyde O-methyl oxime
Ketoxime ether Ketoxime ether.png
Amide Amide.png
Lactam Lactam.png
Carbamic acid Carbamic acid.png
Carbamate Carbamate.png
Urea Urea.png
Isourea Isourea.png
Carbamic acyl halide Carbamic acyl halide.png
Hydroxamic acid Hydroxamic acid.png
Imide Imide.png
Imidoester Imidoester.png
Imidoyl halide Imidoyl halide.png
Hydrazide Hydrazide.png
Cyanate Cyanate.png
Isocyanate Isocyanate.png
Nitro compound Nitro compound.png
Nitroso Nitroso.png
Nitrite Nitrite.png
Nitrate Nitrate.png
Acyl cyanide Acylcyanide.png Propionyl cyanide.png Propionyl cyanide
Semicarbazide Semicarbazide.png
Semicarbazone Semicarbazone.png

Sulfur based

Chemical class Group Formula Structural Formula Prefix Suffix Example
Thioether Thioether RSR' Thioether.png thioalkoxy- -thioether File:.png
Thiol RSH Thiol.png thioxy- -thiol Butan-1-ol.png n-Butanol (Butan-1-ol)
Thial / Thioaldehyde RCHS File:Thioaldehyde.png File:.png
Thione / Thioketone RCSR' File:Thioketone.png File:.png
[[Thioic O-acid]] RC(S)OH File:Thioic O-acid.png File:.png
[[Thioic S-acid]] RC(O)SH File:Thioic S-acid.png File:.png
Dithioic acid RCS2H File:Dithioic acid.png File:.png
Thioyl_halide RCSX File:Thioyl halide.png File:.png
[[Thioic O-ester]] RC(S)OR' File:Thioic O-ester.png File:.png
[[Thioic S-ester]] RC(O)SR' File:Thioic S-ester.png File:.png
Dithioic ester RCS2R' File:Dithioic acid.png File:.png

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