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Chemistry LibreTexts

Functional groups A

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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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Functional groups A is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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