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Functional group
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<h2 id="table-of-common-functional-groups">Table of common functional groups</h2> <p>The following is a list of common functional groups.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> In the formulas, the symbols R and R' usually denote an attached hydrogen, or a <a href="/facts/Hydrocarbon/Dcg95Ju5">hydrocarbon</a> <a href="/facts/Side_chain/Lw8KPAXn">side chain</a> of any length, but may sometimes refer to any group of atoms. </p> <h3>Hydrocarbons</h3> <p>Hydrocarbons are a class of molecule that is defined by functional groups called hydrocarbyls that contain only carbon and hydrogen, but vary in the number and order of double bonds. Each one differs in type (and scope) of reactivity. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural Formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Alkane/Qam7Hvmf">Alkane</a></td><td><a href="/facts/Alkyl/vmEk8X4v">Alkyl</a></td><td>R(CH2)nH</td><td></td><td>alkyl-</td><td>-ane</td><td><a href="/facts/Ethane/BGCzc6yh">Ethane</a></td></tr><tr><td><a href="/facts/Alkene/RtYcS6kU">Alkene</a></td><td><a href="/facts/Alkene/RtYcS6kU">Alkenyl</a></td><td>R2C=CR2</td><td></td><td>alkenyl-</td><td>-ene</td><td><a href="/facts/Ethylene/QMNBYLYn">Ethylene</a><i>(Ethene)</i></td></tr><tr><td><a href="/facts/Alkyne/VHI4N5Wo">Alkyne</a></td><td><a href="/facts/Alkyne/VHI4N5Wo">Alkynyl</a></td><td>RC≡CR′</td><td> R − C ≡ C − R ′ {\displaystyle {\ce {R-C#C-R'}}} </td><td>alkynyl-</td><td>-yne</td><td> H − C ≡ C − H {\displaystyle {\ce {H-C#C-H}}} <a href="/facts/Acetylene/yaDh6cmJ">Acetylene</a><i>(Ethyne)</i></td></tr><tr><td><a href="/facts/Benzene/Fguue7nr">Benzene derivative</a></td><td><a href="/facts/Phenyl/Ql9Yx5uu">Phenyl</a></td><td>RC6H5RPh</td><td></td><td>phenyl-</td><td>-benzene</td><td><a href="/facts/Cumene/uNbTBzE3">Cumene</a><i>(Isopropylbenzene)</i></td></tr></tbody></table> <p>There are also a large number of branched or ring alkanes that have specific names, e.g., <a href="/facts/Tert-butyl/fbTF0UkI">tert-butyl</a>, <a href="/facts/Bornyl/ga7HozH0">bornyl</a>, <a href="/facts/Cyclohexyl/FDAW5j8v">cyclohexyl</a>, etc. There are several functional groups that contain an alkene such as <a href="/facts/Vinyl_group/SyXSgVnw">vinyl group</a>, <a href="/facts/Allyl_group/CDxPwyvF">allyl group</a>, or <a href="/facts/Acryl/gAflh5z4">acrylic group</a>. Hydrocarbons may form charged structures: positively charged <a href="/facts/Carbocation/vIggUxTh">carbocations</a> or negative <a href="/facts/Carbanion/AyYH2udQ">carbanions</a>. Carbocations are often named <i>-um</i>. Examples are <a href="/facts/Tropylium/3vAk8fwQ">tropylium</a> and <a href="/facts/Triphenylmethyl/LqjlIuoH">triphenylmethyl</a> cations and the <a href="/facts/Cyclopentadienyl/2cw59tjx">cyclopentadienyl</a> anion. </p> <h3>Groups containing halogen</h3> <p><a href="/facts/Haloalkane/Enb7LQqt">Haloalkanes</a> are a class of molecule that is defined by a carbon–<a href="/facts/Halogen/YeFgWHeA">halogen</a> bond. This bond can be relatively weak (in the case of an iodoalkane) or quite stable (as in the case of a fluoroalkane). In general, with the exception of <a href="/facts/Fluorination/vYrGVWcJ">fluorinated</a> compounds, haloalkanes readily undergo <a href="/facts/Nucleophilic_substitution/MLLeSsnr">nucleophilic substitution</a> reactions or <a href="/facts/Elimination_reaction/7LSBwU3P">elimination reactions</a>. The substitution on the carbon, the acidity of an adjacent proton, the solvent conditions, etc. all can influence the outcome of the reactivity. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Haloalkane/Enb7LQqt">haloalkane</a></td><td><a href="/facts/Halogen/YeFgWHeA">halo</a></td><td>RX</td><td> R − X {\displaystyle {\ce {R-X}}} </td><td>halo-</td><td>alkyl halide</td><td><a href="/facts/Chloroethane/6DjUIuH7">Chloroethane</a><i>(Ethyl chloride)</i></td></tr><tr><td><a href="/facts/Fluoroalkane/EwWmHflJ">fluoroalkane</a></td><td><a href="/facts/Fluorine/YUV0Fb8m">fluoro</a></td><td>RF</td><td> R − F {\displaystyle {\ce {R-F}}} </td><td>fluoro-</td><td>alkyl fluoride</td><td><a href="/facts/Fluoromethane/RQ9AjAYD">Fluoromethane</a><i>(Methyl fluoride)</i></td></tr><tr><td><a href="/facts/Chloroalkane/IbblBkcB">chloroalkane</a></td><td><a href="/facts/Chlorine/y27UwYBM">chloro</a></td><td>RCl</td><td> R − Cl {\displaystyle {\ce {R-Cl}}} </td><td>chloro-</td><td>alkyl chloride</td><td><a href="/facts/Chloromethane/DvmeEgDS">Chloromethane</a><i>(Methyl chloride)</i></td></tr><tr><td><a href="/facts/Bromoalkane/7v9NP0Ak">bromoalkane</a></td><td><a href="/facts/Bromine/oLfj3C7D">bromo</a></td><td>RBr</td><td> R − Br {\displaystyle {\ce {R-Br}}} </td><td>bromo-</td><td>alkyl bromide</td><td><a href="/facts/Bromomethane/swSGzwnr">Bromomethane</a><i>(Methyl bromide)</i></td></tr><tr><td><a href="/facts/Iodoalkane/P6LDC4IP">iodoalkane</a></td><td><a href="/facts/Iodine/JlfMecMf">iodo</a></td><td>RI</td><td> R − I {\displaystyle {\ce {R-I}}} </td><td>iodo-</td><td>alkyl iodide</td><td><a href="/facts/Iodomethane/uUKdue80">Iodomethane</a><i>(Methyl iodide)</i></td></tr></tbody></table> <h3>Groups containing oxygen</h3> <p>Compounds that contain C–O bonds each possess differing reactivity based upon the location and <a href="/facts/Orbital_hybridisation/Fl7sz8Jm">hybridization</a> of the C–O bond, owing to the electron-withdrawing effect of sp-hybridized oxygen (carbonyl groups) and the donating effects of sp2-hybridized oxygen (alcohol groups). </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">Alcohol</a></td><td><a href="/facts/Hydroxy/Y3Sn2cfq">Hydroxy</a></td><td>ROH</td><td></td><td>hydroxy-</td><td>-ol</td><td><a href="/facts/Methanol/EIfpoNCg">Methanol</a></td></tr><tr><td><a href="/facts/Ketone/BqQXpLo4">Ketone</a></td><td><a href="/facts/Ketone/BqQXpLo4">Ketone</a></td><td>RCOR′</td><td></td><td>-oyl- (-COR′)oroxo- (=O)</td><td>-one</td><td><a href="/facts/Butanone/kMEw9hTq">Butanone</a><i>(Methyl ethyl ketone)</i></td></tr><tr><td><a href="/facts/Aldehyde/xSIRkW03">Aldehyde</a></td><td><a href="/facts/Aldehyde/xSIRkW03">Aldehyde</a></td><td>RCHO</td><td></td><td>formyl- (-COH)oroxo- (=O)</td><td>-al</td><td><a href="/facts/Acetaldehyde/QllLbSUe">Acetaldehyde</a><i>(Ethanal)</i></td></tr><tr><td><a href="/facts/Acyl_halide/2EdXuvun">Acyl halide</a></td><td>Haloformyl</td><td>RCOX</td><td></td><td>carbonofluoridoyl-carbonochloridoyl-carbonobromidoyl-carbonoiodidoyl-</td><td>-oyl fluoride -oyl chloride -oyl bromide -oyl iodide</td><td><a href="/facts/Acetyl_chloride/SU9Bq4tG">Acetyl chloride</a><i>(Ethanoyl chloride)</i></td></tr><tr><td><a href="/facts/Carbonate_ester/4L0jLRBo">Carbonate</a></td><td><a href="/facts/Carbonate_ester/4L0jLRBo">Carbonate ester</a></td><td>ROCOOR′</td><td></td><td>(alkoxycarbonyl)oxy-</td><td>alkyl carbonate</td><td><a href="/facts/Triphosgene/Qo6Krohd">Triphosgene</a><i>(bis(trichloromethyl) carbonate)</i></td></tr><tr><td><a href="/facts/Carboxylic_acid/U4xuMosy">Carboxylate</a></td><td><a href="/facts/Carboxylate/vEDekXRr">Carboxylate</a></td><td>RCOO−</td><td></td><td>carboxylato-</td><td>-oate</td><td><a href="/facts/Sodium_acetate/CU1Yc8Jp">Sodium acetate</a><i>(Sodium ethanoate)</i></td></tr><tr><td><a href="/facts/Carboxylic_acid/U4xuMosy">Carboxylic acid</a></td><td><a href="/facts/Carboxyl/U4xuMosy">Carboxyl</a></td><td>RCOOH</td><td></td><td>carboxy-</td><td>-oic acid</td><td><a href="/facts/Acetic_acid/uyBKA2Pd">Acetic acid</a><i>(Ethanoic acid)</i></td></tr><tr><td><a href="/facts/Ester/FoUAIIw4">Ester</a></td><td><a href="/facts/Ester/FoUAIIw4">Carboalkoxy</a></td><td>RCOOR′</td><td></td><td>alkanoyloxy-oralkoxycarbonyl</td><td>alkyl alkanoate</td><td><a href="/facts/Ethyl_butyrate/mY5Rx3eL">Ethyl butyrate</a><i>(Ethyl butanoate)</i></td></tr><tr><td><a href="/facts/Organic_peroxide/UAyyVaDU">Hydroperoxide</a></td><td><a href="/facts/Organic_peroxide/UAyyVaDU">Hydroperoxy</a></td><td>ROOH</td><td></td><td>hydroperoxy-</td><td>alkyl hydroperoxide</td><td><a href="/facts/Tert-Butyl_hydroperoxide/kDNH7oSM"><i>tert</i>-Butyl hydroperoxide</a></td></tr><tr><td><a href="/facts/Organic_peroxide/UAyyVaDU">Peroxide</a></td><td><a href="/facts/Organic_peroxide/UAyyVaDU">Peroxy</a></td><td>ROOR′</td><td></td><td>peroxy-</td><td>alkyl peroxide</td><td><a href="/facts/Di-tert-butyl_peroxide/FKqXlKUM">Di-tert-butyl peroxide</a></td></tr><tr><td><a href="/facts/Ether/jwDg0IKr">Ether</a></td><td><a href="/facts/Ether/jwDg0IKr">Ether</a></td><td>ROR′</td><td></td><td>alkoxy-</td><td>alkyl ether</td><td><a href="/facts/Diethyl_ether/Ep20vEdj">Diethyl ether</a><i>(Ethoxyethane)</i></td></tr><tr><td><a href="/facts/Hemiacetal/1NRctD1e">Hemiacetal</a></td><td><a href="/facts/Hemiacetal/1NRctD1e">Hemiacetal</a></td><td>R2CH(OR1)(OH)</td><td></td><td>alkoxy -ol</td><td>-al alkyl hemiacetal</td><td></td></tr><tr><td><a href="/facts/Hemiketal/1NRctD1e">Hemiketal</a></td><td><a href="/facts/Hemiketal/1NRctD1e">Hemiketal</a></td><td>RC(ORʺ)(OH)R′</td><td></td><td>alkoxy -ol</td><td>-one alkyl hemiketal</td><td></td></tr><tr><td><a href="/facts/Acetal/DuwXfBMz">Acetal</a></td><td><a href="/facts/Acetal/DuwXfBMz">Acetal</a></td><td>RCH(OR′)(OR″)</td><td></td><td>dialkoxy-</td><td>-al dialkyl acetal</td><td></td></tr><tr><td><a href="/facts/Ketal/DuwXfBMz">Ketal</a> (or <a href="/facts/Acetal/DuwXfBMz">Acetal</a>)</td><td><a href="/facts/Ketal/DuwXfBMz">Ketal</a> (or <a href="/facts/Acetal/DuwXfBMz">Acetal</a>)</td><td>RC(OR″)(OR‴)R′</td><td></td><td>dialkoxy-</td><td>-one dialkyl ketal</td><td></td></tr><tr><td><a href="/facts/Orthoester/CAcYfE2V">Orthoester</a></td><td><a href="/facts/Orthoester/CAcYfE2V">Orthoester</a></td><td>RC(OR′)(OR″)(OR‴)</td><td></td><td>trialkoxy-</td><td></td><td></td></tr><tr><td><a href="/facts/Heterocycle/8oYSjJxY">Heterocycle</a> (if cyclic)</td><td><a href="/facts/Methylenedioxy/VltTYSFh">Methylenedioxy</a></td><td>(–OCH2O–)</td><td></td><td>methylenedioxy-</td><td>-dioxole</td><td><a href="/facts/1%2c3-Benzodioxole/28fM0bEQ">1,2-Methylenedioxybenzene</a><i>(1,3-Benzodioxole)</i></td></tr><tr><td><a href="/facts/Orthocarbonate_ester/qFtKVJx4">Orthocarbonate ester</a></td><td><a href="/facts/Orthocarbonate_ester/qFtKVJx4">Orthocarbonate ester</a></td><td>C(OR)(OR′)(OR″)(OR‴)</td><td></td><td>tetralkoxy-</td><td><i>tetraalkyl</i> orthocarbonate</td><td><a href="/facts/Tetramethoxymethane/rEh706vB">Tetramethoxymethane</a></td></tr><tr><td><a href="/facts/Organic_acid_anhydride/9YnWCsJo">Organic acid anhydride</a></td><td><a href="/facts/Carboxylic_anhydride/9YnWCsJo">Carboxylic anhydride</a></td><td>R1(CO)O(CO)R2</td><td></td><td></td><td>anhydride</td><td><a href="/facts/Butyric_anhydride/hH0LeYKm">Butyric anhydride</a></td></tr></tbody></table> <h3>Groups containing nitrogen</h3> <p>Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of <a href="/facts/Amide/C6kCzYEA">amides</a>. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Amide/C6kCzYEA">Amide</a></td><td><a href="/facts/Carboxamide/C6kCzYEA">Carboxamide</a></td><td>RCONR'R"</td><td></td><td>carboxamido-orcarbamoyl-</td><td>-amide</td><td><a href="/facts/Acetamide/3coa1Ez5">Acetamide</a><i>(Ethanamide)</i></td></tr><tr><td><a href="/facts/Amidine/dhB1LGfz">Amidine</a></td><td><a href="/facts/Amidine/dhB1LGfz">Amidine</a></td><td>R4C(NR1)(NR2R3)</td><td></td><td>amidino-</td><td>-amidine</td><td>acetamidine<p>(acetimidamide)</p></td></tr><tr><td><a href="/facts/Guanidine/lGzDoPuJ">Guanidine</a></td><td><a href="/facts/Guanidine/lGzDoPuJ">Guanidine</a></td><td>RNC(NR2)2)</td><td></td><td>Guanidin-</td><td>-Guanidine</td><td>Guanidinopropionic acid</td></tr><tr><td rowspan="5"><a href="/facts/Amine/SN7W44fv">Amines</a></td><td><a href="/facts/Amine/SN7W44fv">Primary amine</a></td><td>RNH2</td><td></td><td>amino-</td><td>-amine</td><td><a href="/facts/Methylamine/srMMDp0D">Methylamine</a><i>(Methanamine)</i></td></tr><tr><td><a href="/facts/Amine/SN7W44fv">Secondary amine</a></td><td>R'R"NH</td><td></td><td>amino-</td><td>-amine</td><td><a href="/facts/Dimethylamine/6ehYB5m0">Dimethylamine</a></td></tr><tr><td><a href="/facts/Amine/SN7W44fv">Tertiary amine</a></td><td>R3N</td><td></td><td>amino-</td><td>-amine</td><td><a href="/facts/Trimethylamine/cj1dWmJq">Trimethylamine</a></td></tr><tr><td><a href="/facts/Quaternary_ammonium_cation/bNpF1goc">4° ammonium ion</a></td><td>R4N+</td><td></td><td>ammonio-</td><td>-ammonium</td><td><a href="/facts/Choline/wf9EVzfx">Choline</a></td></tr><tr><td><a href="/facts/Hydrazone/XsIDpYpW">Hydrazone</a></td><td>R'R"CN2H2</td><td></td><td>hydrazino-</td><td>-hydrazine</td><td></td></tr><tr><td rowspan="4"><a href="/facts/Imine/yK72z07j">Imine</a></td><td><a href="/facts/Imine/yK72z07j">Primary ketimine</a></td><td>RC(=NH)R'</td><td></td><td>imino-</td><td>-imine</td><td></td></tr><tr><td><a href="/facts/Imine/yK72z07j">Secondary ketimine</a></td><td> RC ( = NR ″ ) R ′ {\displaystyle {\ce {RC(=NR'')R'}}} </td><td></td><td>imino-</td><td>-imine</td><td></td></tr><tr><td><a href="/facts/Imine/yK72z07j">Primary aldimine</a></td><td>RC(=NH)H</td><td></td><td>imino-</td><td>-imine</td><td><a href="/facts/Ethanimine/VA1vBvj3">Ethanimine</a></td></tr><tr><td><a href="/facts/Imine/yK72z07j">Secondary aldimine</a></td><td>RC(=NR')H</td><td></td><td>imino-</td><td>-imine</td><td></td></tr><tr><td><a href="/facts/Imide/0v1JMJt2">Imide</a></td><td><a href="/facts/Imide/0v1JMJt2">Imide</a></td><td>(RCO)2NR'</td><td></td><td>imido-</td><td>-imide</td><td><a href="/facts/Succinimide/v3eRV6hY">Succinimide</a>(Pyrrolidine-2,5-dione)</td></tr><tr><td><a href="/facts/Azide/AaJwyv1z">Azide</a></td><td><a href="/facts/Azide/AaJwyv1z">Azide</a></td><td>RN3</td><td></td><td>azido-</td><td>alkyl azide</td><td><a href="/facts/Phenyl_azide/tczBhkqK">Phenyl azide</a>(Azidobenzene)</td></tr><tr><td><a href="/facts/Azo_compound/dnl1WKnK">Azo compound</a></td><td><a href="/facts/Azo_compound/dnl1WKnK">Azo(Diimide)</a></td><td>RN2R'</td><td></td><td>azo-</td><td>-diazene</td><td><a href="/facts/Methyl_orange/GQLXo1Pl">Methyl orange</a>(p-dimethylamino-azobenzenesulfonic acid)</td></tr><tr><td rowspan="2"><a href="/facts/Cyanate/EcDWGQQh">Cyanates</a></td><td><a href="/facts/Cyanate/EcDWGQQh">Cyanate</a></td><td>ROCN</td><td></td><td>cyanato-</td><td>alkyl cyanate</td><td>Methyl cyanate</td></tr><tr><td><a href="/facts/Isocyanate/YYDoDBgp">Isocyanate</a></td><td>RNCO</td><td></td><td>isocyanato-</td><td>alkyl isocyanate</td><td><a href="/facts/Methyl_isocyanate/N9hgqxLe">Methyl isocyanate</a></td></tr><tr><td><a href="/facts/Nitrate/5AnVlYnL">Nitrate</a></td><td><a href="/facts/Nitrate/5AnVlYnL">Nitrate</a></td><td>RONO2</td><td></td><td>nitrooxy-, nitroxy-</td><td><p>alkyl nitrate</p></td><td><a href="/facts/Amyl_nitrate/BnjJdV21">Amyl nitrate</a><i>(1-nitrooxypentane)</i></td></tr><tr><td rowspan="2"><a href="/facts/Nitrile/Gz7RCnC6">Nitrile</a></td><td><a href="/facts/Nitrile/Gz7RCnC6">Nitrile</a></td><td>RCN</td><td> R − ≡ N {\displaystyle {\ce {R-\!#N}}} </td><td>cyano-</td><td>alkanenitrilealkyl cyanide</td><td><a href="/facts/Benzonitrile/6a7FLvHq">Benzonitrile</a><i>(Phenyl cyanide)</i></td></tr><tr><td><a href="/facts/Isonitrile/VmkIBMKR">Isonitrile</a></td><td>RNC</td><td></td><td>isocyano-</td><td>alkaneisonitrilealkyl isocyanide</td><td> H 3 C − N + ≡ C − {\displaystyle {\ce {H3C}}{-}{\overset {+}{{\ce {N}}}}{\ce {#C^-}}} <a href="/facts/Methyl_isocyanide/xKLjwVhm">Methyl isocyanide</a></td></tr><tr><td><a href="/facts/Alkyl_nitrites/A9QmA4ho">Nitrite</a></td><td><a href="/facts/Alkyl_nitrites/A9QmA4ho">Nitrosooxy</a></td><td>RONO</td><td></td><td>nitrosooxy-</td><td><p>alkyl nitrite</p></td><td><a href="/facts/Isoamyl_nitrite/xGGc9ITL">Isoamyl nitrite</a><i>(3-methyl-1-nitrosooxybutane)</i></td></tr><tr><td><a href="/facts/Nitro_compound/pem2BhMY">Nitro compound</a></td><td><a href="/facts/Nitro_functional_group/pem2BhMY">Nitro</a></td><td>RNO2</td><td></td><td>nitro-</td><td> </td><td><a href="/facts/Nitromethane/mfVA2AA1">Nitromethane</a></td></tr><tr><td><a href="/facts/Nitroso/Irref1C6">Nitroso compound</a></td><td><a href="/facts/Nitroso/Irref1C6">Nitroso</a></td><td>RNO</td><td></td><td>nitroso- (Nitrosyl-)</td><td> </td><td><a href="/facts/Nitrosobenzene/UeJYNT1R">Nitrosobenzene</a></td></tr><tr><td><a href="/facts/Oxime/xRlPfB6K">Oxime</a></td><td><a href="/facts/Oxime/xRlPfB6K">Oxime</a></td><td>RCH=NOH</td><td></td><td> </td><td><a href="/facts/Oxime/xRlPfB6K">Oxime</a></td><td><a href="/facts/Acetone_oxime/XEg6rBG8">Acetone oxime</a><i>(2-Propanone oxime)</i></td></tr><tr><td><a href="/facts/Pyridine/X817hCch">Pyridine derivative</a></td><td><a href="/facts/Pyridine/X817hCch">Pyridyl</a></td><td>RC5H4N</td><td></td><td><p>4-pyridyl(pyridin-4-yl)</p><p>3-pyridyl(pyridin-3-yl)</p><p>2-pyridyl(pyridin-2-yl)</p></td><td>-pyridine</td><td><a href="/facts/Nicotine/VQ6HcIrY">Nicotine</a></td></tr><tr><td><a href="/facts/Carbamate/3lNmyxgQ">Carbamate ester</a></td><td><a href="/facts/Carbamate/3lNmyxgQ">Carbamate</a></td><td>RO(C=O)NR2</td><td></td><td>(-carbamoyl)oxy-</td><td>-carbamate</td><td><a href="/facts/Chlorpropham/D8PwroVU">Chlorpropham</a><i>(Isopropyl (3-chlorophenyl)carbamate)</i></td></tr></tbody></table> <h3>Groups containing sulfur</h3> <p>Compounds that contain sulfur exhibit unique chemistry due to sulfur's ability to form more bonds than oxygen, its lighter analogue on the periodic table. Substitutive nomenclature (marked as prefix in table) is preferred over functional class nomenclature (marked as suffix in table) for sulfides, disulfides, sulfoxides and sulfones. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Thiol/VemKEDP9">Thiol</a></td><td><a href="/facts/Thiol/VemKEDP9">Sulfhydryl</a></td><td>RSH</td><td></td><td>sulfanyl-(-SH)</td><td>-thiol</td><td><a href="/facts/Ethanethiol/3zjKzHH4">Ethanethiol</a></td></tr><tr><td><a href="/facts/Sulfide_(organic)/GdyEz43f">Sulfide</a>(<a href="/facts/Thioether/GdyEz43f">Thioether</a>)</td><td><a href="/facts/Sulfide_(organic)/GdyEz43f">Sulfide</a></td><td>RSR'</td><td></td><td><i>substituent</i> sulfanyl-(-SR')</td><td>di(<i>substituent</i>) sulfide</td><td><a href="/facts/(Methylsulfanyl)methane/mUrg1jol">(Methylsulfanyl)methane</a> (prefix) or<a href="/facts/Dimethyl_sulfide/mUrg1jol">Dimethyl sulfide</a> (suffix)</td></tr><tr><td><a href="/facts/Disulfide_bond/eDx5Xtlg">Disulfide</a></td><td><a href="/facts/Disulfide/eDx5Xtlg">Disulfide</a></td><td>RSSR'</td><td></td><td><i>substituent</i> disulfanyl-(-SSR')</td><td>di(<i>substituent</i>) disulfide</td><td><a href="/facts/(Methyldisulfanyl)methane/XJE2Ge8b">(Methyldisulfanyl)methane</a> (prefix) or<a href="/facts/Dimethyl_disulfide/XJE2Ge8b">Dimethyl disulfide</a> (suffix)</td></tr><tr><td><a href="/facts/Sulfoxide/Stk3Vnj9">Sulfoxide</a></td><td><a href="/facts/Sulfoxide/Stk3Vnj9">Sulfinyl</a></td><td>RSOR'</td><td></td><td>-sulfinyl-(-SOR')</td><td>di(<i>substituent</i>) sulfoxide</td><td><a href="/facts/(Methanesulfinyl)methane/T4HSYfuC">(Methanesulfinyl)methane</a> (prefix) or<a href="/facts/Dimethyl_sulfoxide/T4HSYfuC">Dimethyl sulfoxide</a> (suffix)</td></tr><tr><td><a href="/facts/Sulfone/LJLP1RcT">Sulfone</a></td><td><a href="/facts/Sulfone/LJLP1RcT">Sulfonyl</a></td><td>RSO2R'</td><td></td><td>-sulfonyl-(-SO2R')</td><td>di(<i>substituent</i>) sulfone</td><td><a href="/facts/(Methanesulfonyl)methane/kaBnyAv8">(Methanesulfonyl)methane</a> (prefix) or<a href="/facts/Dimethyl_sulfone/kaBnyAv8">Dimethyl sulfone</a> (suffix)</td></tr><tr><td><a href="/facts/Sulfinic_acid/Ur6P5qNX">Sulfinic acid</a></td><td>Sulfino</td><td>RSO2H</td><td></td><td>sulfino-(-SO2H)</td><td>-sulfinic acid</td><td><a href="/facts/2-Aminoethanesulfinic_acid/KYmlvSNM">2-Aminoethanesulfinic acid</a></td></tr><tr><td><a href="/facts/Sulfonic_acid/6JHPGnNY">Sulfonic acid</a></td><td>Sulfo</td><td>RSO3H</td><td></td><td>sulfo-(-SO3H)</td><td>-sulfonic acid</td><td><a href="/facts/Benzenesulfonic_acid/N8YYycca">Benzenesulfonic acid</a></td></tr><tr><td><a href="/facts/Sulfonate_ester/ApbgQMXB">Sulfonate ester</a></td><td>Sulfo</td><td>RSO3R'</td><td></td><td>(-sulfonyl)oxy-oralkoxysulfonyl-</td><td><i>R'</i> <i>R</i>-sulfonate</td><td><a href="/facts/Methyl_trifluoromethanesulfonate/UEtL9wqD">Methyl trifluoromethanesulfonate</a> orMethoxysulfonyl trifluoromethane (prefix)</td></tr><tr><td rowspan="2"><a href="/facts/Thiocyanate/S438CJp8">Thiocyanate</a></td><td><a href="/facts/Thiocyanate/S438CJp8">Thiocyanate</a></td><td>RSCN</td><td></td><td>thiocyanato-(-SCN)</td><td><i>substituent</i> thiocyanate</td><td>Phenyl thiocyanate</td></tr><tr><td><a href="/facts/Isothiocyanate/zk3Q3Pv8">Isothiocyanate</a></td><td>RNCS</td><td></td><td>isothiocyanato-(-NCS)</td><td><i>substituent</i> isothiocyanate</td><td><a href="/facts/Allyl_isothiocyanate/5b0SaJHF">Allyl isothiocyanate</a></td></tr><tr><td><a href="/facts/Thioketone/wMf09spv">Thioketone</a></td><td><a href="/facts/Carbonothioyl/wMf09spv">Carbonothioyl</a></td><td>RCSR'</td><td></td><td>-thioyl-(-CSR')orsulfanylidene-(=S)</td><td>-thione</td><td><a href="/facts/Diphenylmethanethione/uGLq241E">Diphenylmethanethione</a>(<a href="/facts/Thiobenzophenone/uGLq241E">Thiobenzophenone</a>)</td></tr><tr><td><a href="/facts/Thial/PdqABLbb">Thial</a></td><td><a href="/facts/Carbonothioyl/wMf09spv">Carbonothioyl</a></td><td>RCSH</td><td></td><td>methanethioyl-(-CSH)orsulfanylidene-(=S)</td><td>-thial</td><td></td></tr><tr><td rowspan="2"><a href="/facts/Thiocarboxylic_acid/x9e73QKY">Thiocarboxylic acid</a></td><td>Carbothioic <i>S</i>-acid</td><td>RC=OSH</td><td></td><td>mercaptocarbonyl-</td><td>-thioic <i>S</i>-acid</td><td><a href="/facts/Thiobenzoic_acid/nnUAuEcz">Thiobenzoic acid</a><i>(benzothioic </i>S<i>-acid)</i></td></tr><tr><td>Carbothioic <i>O</i>-acid</td><td>RC=SOH</td><td></td><td>hydroxy(thiocarbonyl)-</td><td>-thioic <i>O</i>-acid</td><td></td></tr><tr><td rowspan="2"><a href="/facts/Thioester/UwfKqs1F">Thioester</a></td><td>Thiolester</td><td>RC=OSR'</td><td></td><td></td><td><i>S</i>-alkyl-alkane-thioate</td><td>S-Methyl thioacrylate<i>(</i>S<i>-Methyl prop-2-enethioate)</i></td></tr><tr><td>Thionoester</td><td>RC=SOR'</td><td></td><td></td><td><i>O</i>-alkyl-alkane-thioate</td><td></td></tr><tr><td><a href="/facts/Thiocarboxylic_acid/x9e73QKY">Dithiocarboxylic acid</a></td><td>Carbodithioic acid</td><td>RCS2H</td><td></td><td>dithiocarboxy-</td><td>-dithioic acid</td><td><a href="/facts/Dithiobenzoic_acid/z1Re3jvD">Dithiobenzoic acid</a><i>(Benzenecarbodithioic acid)</i></td></tr><tr><td>Dithiocarboxylic acid ester</td><td>Carbodithio</td><td>RC=SSR'</td><td></td><td></td><td>-dithioate</td><td></td></tr></tbody></table> <h3>Groups containing phosphorus</h3> <p>Compounds that contain phosphorus exhibit unique chemistry due to the ability of phosphorus to form more bonds than nitrogen, its lighter analogue on the periodic table. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Phosphine/aYysn5TS">Phosphine</a>(<a href="/facts/Phosphane/aYysn5TS">Phosphane</a>)</td><td>Phosphino</td><td>R3P</td><td></td><td>phosphanyl-</td><td>-phosphane</td><td>Methylpropylphosphane</td></tr><tr><td><a href="/facts/Phosphonic_acid/4A4bHBTw">Phosphonic acid</a></td><td>Phosphono</td><td> RP ( = O ) ( OH ) 2 {\displaystyle {\ce {RP(=O)(OH)2}}} </td><td></td><td>phosphono-</td><td><i>substituent</i> phosphonic acid</td><td>Benzylphosphonic acid</td></tr><tr><td rowspan="2"><a href="/facts/Phosphate/FDGVCxUG">Phosphate</a></td><td rowspan="2">Phosphate</td><td rowspan="2"> ROP ( = O ) ( OH ) 2 {\displaystyle {\ce {ROP(=O)(OH)2}}} </td><td rowspan="2"></td><td rowspan="2">phosphonooxy-or<i>O</i>-phosphono- (phospho-)</td><td rowspan="2"><i>substituent</i> phosphate</td><td><a href="/facts/Glyceraldehyde_3-phosphate/Wy3FMLzJ">Glyceraldehyde 3-phosphate</a> (suffix)</td></tr><tr><td><i>O</i>-Phosphonocholine (prefix)(<a href="/facts/Phosphocholine/qMJ6dxMe">Phosphocholine</a>)</td></tr><tr><td rowspan="2"><a href="/facts/Phosphodiester_bonds/fCjTAnxa">Phosphodiester</a></td><td rowspan="2"><a href="/facts/Phosphate/FDGVCxUG">Phosphate</a></td><td rowspan="2">HOPO(OR)2</td><td rowspan="2"></td><td rowspan="2">[(alkoxy)hydroxyphosphoryl]oxy-or<i>O</i>-[(alkoxy)hydroxyphosphoryl]-</td><td rowspan="2">di(<i>substituent</i>) hydrogen phosphateorphosphoric acid di(<i>substituent</i>) ester</td><td><a href="/facts/DNA/nB89Iauz">DNA</a></td></tr><tr><td><i>O</i>‑[(2‑Guanidinoethoxy)hydroxyphosphoryl]‑l‑serine (prefix)(<a href="/facts/Lombricine/gNCt7y5R">Lombricine</a>)</td></tr></tbody></table> <h3>Groups containing boron</h3> <p>Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as <a href="/facts/Lewis_acid/qlLqRvg2">Lewis acids</a>. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Boronic_acid/BtN4s5B4">Boronic acid</a></td><td>Borono</td><td>RB(OH)2</td><td></td><td>Borono-</td><td><i>substituent</i>boronic acid</td><td><a href="/facts/Phenylboronic_acid/oMJfLBY7">Phenylboronic acid</a></td></tr><tr><td><a href="/facts/Boronic_acid/BtN4s5B4">Boronic ester</a></td><td>Boronate</td><td>RB(OR)2</td><td></td><td>O-[bis(alkoxy)alkylboronyl]-</td><td><i>substituent</i>boronic aciddi(<i>substituent</i>) ester</td><td></td></tr><tr><td><a href="/facts/Borinic_acid/r1MD19Ju">Borinic acid</a></td><td>Borino</td><td>R2BOH</td><td></td><td>Hydroxyborino-</td><td>di(<i>substituent</i>)borinic acid</td><td></td></tr><tr><td><a href="/facts/Boronic_acid/BtN4s5B4">Borinic ester</a></td><td>Borinate</td><td>R2BOR</td><td></td><td>O-[alkoxydialkylboronyl]-</td><td>di(<i>substituent</i>)borinic acid<i>substituent</i> ester</td><td>Diphenylborinic acid 2-aminoethyl ester(<a href="/facts/2-Aminoethoxydiphenyl_borate/QmEc78u1">2-Aminoethoxydiphenyl borate</a>)</td></tr></tbody></table> <h3>Groups containing metals</h3> <table><tbody><tr><th>Chemical class</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td><a href="/facts/Organolithium_reagent/xgYnjhP3">Alkyllithium</a></td><td>RLi</td><td rowspan="4">(tri/di)alkyl-</td><td>-lithium</td><td><p><a href="/facts/Methyllithium/Fo5UzmsP">methyllithium</a></p></td></tr><tr><td><a href="/facts/Grignard_reagent/0vkLtPo1">Alkylmagnesium halide</a></td><td>RMgX (X=Cl, Br, I)[note 1]</td><td>-magnesium halide</td><td><p><a href="/facts/Methylmagnesium_chloride/fpqQ5eBV">methylmagnesium chloride</a></p></td></tr><tr><td>Alkylaluminium</td><td>Al2R6</td><td>-aluminium</td><td><p><a href="/facts/Trimethylaluminium/QxlKB90v">trimethylaluminium</a></p></td></tr><tr><td><a href="/facts/Silyl_ether/k6y8Th9E">Silyl ether</a></td><td>R3SiOR</td><td>-silyl ether</td><td><p><a href="/facts/Trimethylsilyl_trifluoromethanesulfonate/NhKjtHxd">trimethylsilyl triflate</a></p></td></tr></tbody></table> <p>note 1 <a href="/facts/Fluorine/YUV0Fb8m">Fluorine</a> is too electronegative to be bonded to magnesium; it becomes an <a href="/facts/Salt_(chemistry)/lsSKwGpn">ionic salt</a> instead. </p> <h3>Names of radicals or moieties</h3> <p>These names are used to refer to the moieties themselves or to radical species, and also to form the names of halides and substituents in larger molecules. </p><p>When the parent hydrocarbon is unsaturated, the suffix ("-yl", "-ylidene", or "-ylidyne") replaces "-ane" (e.g. "ethane" becomes "ethyl"); otherwise, the suffix replaces only the final "-e" (e.g. "<a href="/facts/Ethyne/yaDh6cmJ">ethyne</a>" becomes "<a href="/facts/Ethynyl/V0jjylSd">ethynyl</a>").<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p><p>When used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a <a href="/facts/Methylene_bridge/t3lvUJuT">methylene bridge</a> (methanediyl) has two single bonds, whereas a <a href="/facts/Methylidene_group/bEIzaSd0">methylidene group</a> (methylidene) has one double bond. Suffixes can be combined, as in methylidyne (triple bond) vs. methylylidene (single bond and double bond) vs. methanetriyl (three double bonds). </p><p>There are some retained names, such as <a href="/facts/Methylene_group/sdGv7zMu">methylene</a> for methanediyl, 1,x-<a href="/facts/Phenylene/r983dBRL">phenylene</a> for phenyl-1,x-diyl (where x is 2, 3, or 4),<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> <a href="/facts/Carbyne/rxFKkHCM">carbyne</a> for methylidyne, and <a href="/facts/Trityl/35o8VWeP">trityl</a> for triphenylmethyl. </p> <table><tbody><tr><th><a href="/facts/Chemical_class/ePAxWT8S">Chemical class</a></th><th>Group</th><th>Formula</th><th>Structural formula</th><th>Prefix</th><th>Suffix</th><th>Example</th></tr><tr><td>Single bond</td><td></td><td>R•</td><td></td><td>Ylo-<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a></td><td>-yl</td><td><a href="/facts/Methyl_group/fkM97EMD">Methyl group</a><a href="/facts/Methyl_radical/TYS25r9w">Methyl radical</a></td></tr><tr><td>Double bond</td><td></td><td>R:</td><td></td><td>?</td><td>-ylidene</td><td><a href="/facts/Methylidene/vIPU9NXl">Methylidene</a></td></tr><tr><td>Triple bond</td><td></td><td>R⫶</td><td></td><td>?</td><td>-ylidyne</td><td><a href="/facts/Methylidyne/4ExL1FTq">Methylidyne</a></td></tr><tr><td>Carboxylic <a href="/facts/Acyl/1vRPrmUX">acyl</a> radical</td><td>Acyl</td><td>R−C(=O)•</td><td></td><td>?</td><td>-oyl</td><td><a href="/facts/Acetyl/rRmtXdn3">Acetyl</a></td></tr></tbody></table> <h2 id="see-also">See also</h2> <ul><li>Category:Functional groups</li> <li><a href="/facts/Group_contribution_method/29UR7szr">Group contribution method</a></li></ul> <h2 id="external-links">External links</h2> Wikimedia Commons has media related to Functional groups. <ul><li><a href="https://www.acdlabs.com/iupac/nomenclature/">IUPAC Blue Book (organic nomenclature)</a></li> <li><a href="https://web.archive.org/web/20070927121055/http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf">"IUPAC ligand abbreviations"</a> (PDF). <a href="/facts/IUPAC/2AV6myCK">IUPAC</a>. 2 April 2004. Archived from <a href="http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf">the original</a> (PDF) on 27 September 2007. Retrieved 25 February 2015.</li> <li><a href="https://www.pearson.com/channels/organic-chemistry/learn/johnny/molecular-representations/functional-groups">Functional group video</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Compendium of Chemical Terminology (IUPAC "Gold Book") functional group Archived 2019-05-16 at the Wayback Machine <a href="/wiki/Compendium_of_Chemical_Terminology" target="_blank">/wiki/Compendium_of_Chemical_Terminology</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>March, Jerry (1985). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). New York: Wiley. ISBN 9780471854722. OCLC 642506595. <a href="9780471854722" target="_blank">9780471854722</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Brown, Theodore (2002). Chemistry: the central science. Upper Saddle River, NJ: Prentice Hall. p. 1001. ISBN 0130669970. <a href="0130669970" target="_blank">0130669970</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Moss, G. P.; W.H. Powell. "RC-81.1.1. Monovalent radical centers in saturated acyclic and monocyclic hydrocarbons, and the mononuclear EH4 parent hydrides of the carbon family". IUPAC Recommendations 1993. Department of Chemistry, Queen Mary University of London. Archived from the original on 9 February 2015. Retrieved 25 February 2015. <a href="https://web.archive.org/web/20150209155729/http://www.chem.qmul.ac.uk/iupac/ions/RC811.html" target="_blank">https://web.archive.org/web/20150209155729/http://www.chem.qmul.ac.uk/iupac/ions/RC811.html</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>"R-2. 5 Substituent Prefix Names Derived from Parent Hydrides". IUPAC. 1993. Archived from the original on 2019-03-22. Retrieved 2018-12-15. section P-56.2.1 <a href="https://www.acdlabs.com/iupac/nomenclature/93/r93_271.htm" target="_blank">https://www.acdlabs.com/iupac/nomenclature/93/r93_271.htm</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>"Revised Nomenclature for Radicals, Ions, Radical Ions and Related Species (IUPAC Recommendations 1993: RC-81.3. Multiple radical centers)". Archived from the original on 2017-06-11. Retrieved 2014-12-02. <a href="https://web.archive.org/web/20170611171918/http://www.chem.qmul.ac.uk/iupac/ions/RC813.html" target="_blank">https://web.archive.org/web/20170611171918/http://www.chem.qmul.ac.uk/iupac/ions/RC813.html</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> </ol>