Functional groups A
- Page ID
- 22646
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)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 |
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phenyl- | -benzene |  Propylbenzene (Phenylpropane) |
| Toluene derivative | Benzyl | RCH2C6H5 RBn |
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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 |
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| Ketimine / Imine |  |
 Butan-2-imine |
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| Ketenimine |  |
 2-Methylbut-1-en-1-imine |
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| Nitrile / Cyanide |  |
 Butyronitrile 1-Cyanobutane |
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| Isocyanide / Isonitrile |  |
 1-Isocyanopropane 1-Propylisocyanide |
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| Azide |  |
 1-Azidopropane 1-Propylazide |
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| Azo compound / Diimide / Diazene |  |
 (E)-1,2-diethyldiazene (Azoethane) |
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| Diazonium salt |  |
 Butane-2-diazonium (2-Diazobutane) |
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| Carbodiimide |  |
 N,N'-Diisopropylcarbodiimide |
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| Amidine |  |
 Propylamidine |
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| Amidrazone |  |
 Propylamidrazone (Propionimidohydrazide) |
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| Guanidine |  |
 1,3-Diethyl-2-methylguanidine |
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| Hydrazine |  |
 1-Ethyl-2-methylhydrazine |
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| Hydrazone |  |
 Acetone N,N-dimethylhydrazone |
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| Aminal |  |
 Propane-2,2-diamine |
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| Hemiaminal |  |
 2-Aminopropan-2-ol |
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| Enamine |  |
 (Z)-But-2-en-2-amine |
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| Aniline |  |
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| Hydroxylamine |  |
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| Amine oxide / N-oxide |  |
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| Aldoxime |  |
 Propionaldehyde oxime |
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| Ketoxime |  |
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| Aldoxime ether |  |
 Propionaldehyde O-methyl oxime |
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| Ketoxime ether |  |
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| Amide |  |
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| Lactam |  |
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| Carbamic acid |  |
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| Carbamate |  |
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| Urea |  |
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| Isourea |  |
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| Carbamic acyl halide |  |
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| Hydroxamic acid |  |
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| Imide |  |
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| Imidoester |  |
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| Imidoyl halide |  |
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| Hydrazide |  |
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| Cyanate |  |
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| Isocyanate |  |
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| Nitro compound |  |
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| Nitroso |  |
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| Nitrite |  |
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| Nitrate |  |
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| Acyl cyanide |  |
 Propionyl cyanide |
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| Semicarbazide |  |
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| 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 |