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 alkyl- -ane
Butane
Alkene Alkenyl R2C=CR2 alkenyl- -ene
(E)-But-2-ene
Alkyne Alkynyl RC≡CR' alkynyl- -yne
But-2-yne
Allene Allenyl R2C=C=CR2 allenyl- -diene
Penta-2,3-diene
Cumulene Cumulenyl R2C=C=C=CR2 cumulenyl- -triene
Hexa-2,3,4-triene
Benzene derivative Phenyl RC6H5
RPh
phenyl- -benzene
Propylbenzene
(Phenylpropane)
Toluene derivative Benzyl RCH2C6H5
RBn
benzyl- -toluene
Benzylbromide
(α-bromotoluene)
Halide Halo RX halo- -halide
Butyl iodide
(1-Iodobutane)

Oxygen based

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

Nitrogen based

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

Sulfur based

Chemical class Group Formula Structural Formula Prefix Suffix Example
Thioether Thioether RSR' thioalkoxy- -thioether File:.png
Thiol   RSH thioxy- -thiol
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

Contributors

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