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Functional groups A

Last updated

Jan 23, 2023
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- Molecular Classes
- Homolytic C-H Bond Dissociation Energies of Organic Molecules

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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	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	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	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

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Carbon based

Oxygen based

Nitrogen based

Sulfur based

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