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<title>Functional group</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Functional group</span></span>

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</style><div role="note" class="hatnote navigation-not-searchable">For other uses, see <a href="Functional_group_(disambiguation)" class="mw-disambig" title="Functional group (disambiguation)">Functional group (disambiguation)</a>.</div>

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<p>In <a href="Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>functional group</b> is any <a href="Substituent" title="Substituent">substituent</a> or <a href="Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> in a <a href="Molecule" title="Molecule">molecule</a> that causes the molecule's characteristic <a href="Chemical_reaction" title="Chemical reaction">chemical reactions</a>. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> This enables systematic prediction of chemical reactions and behavior of <a href="Chemical_compound" title="Chemical compound">chemical compounds</a> and the design of <a href="Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a>. The <a href="Reactivity_(chemistry)" title="Reactivity (chemistry)">reactivity</a> of a functional group can be modified by other functional groups nearby. <a href="Functional_group_interconversion" class="mw-redirect" title="Functional group interconversion">Functional group interconversion</a> can be used in <a href="Retrosynthetic_analysis" title="Retrosynthetic analysis">retrosynthetic analysis</a> to plan <a href="Organic_synthesis" title="Organic synthesis">organic synthesis</a>.

</p><p>A functional group is a group of atoms in a molecule with distinctive <a href="Chemical_property" title="Chemical property">chemical properties</a>, regardless of the other <a href="Atom" title="Atom">atoms</a> in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by <a href="Covalent_bond" title="Covalent bond">covalent bonds</a>. For repeating units of <a href="Polymer" title="Polymer">polymers</a>, functional groups attach to their <a href="Chemical_polarity" title="Chemical polarity">nonpolar</a> core of <a href="Carbon" title="Carbon">carbon</a> atoms and thus add chemical character to carbon chains. Functional groups can also be <a href="Ionization" title="Ionization">charged</a>, e.g. in <a href="Carboxylate" title="Carboxylate">carboxylate</a> salts (<style data-mw-deduplicate="TemplateStyles:r1123817410">

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</style><span class="chemf nowrap">−COO<sup class="template-chem2-sup">−</sup></span>), which turns the molecule into a <a href="Polyatomic_ion" title="Polyatomic ion">polyatomic ion</a> or a <a href="Coordination_complex" title="Coordination complex">complex ion</a>. Functional groups binding to a central atom in a <a href="Coordination_complex" title="Coordination complex">coordination complex</a> are called <i><a href="Ligand" title="Ligand">ligands</a></i>. Complexation and <a href="Solvation" title="Solvation">solvation</a> are also caused by specific interactions of functional groups. In the common rule of thumb "like dissolves like", it is the shared or mutually well-interacting functional groups which give rise to <a href="Solubility" title="Solubility">solubility</a>. For example, <a href="Sugar" title="Sugar">sugar</a> dissolves in water because both share the <a href="Hydroxy_group" title="Hydroxy group">hydroxyl</a> functional group (<span class="chemf nowrap">−OH</span>) and hydroxyls interact strongly with each other. Plus, when functional groups are more <a href="Electronegativity" title="Electronegativity">electronegative</a> than atoms they attach to, the functional groups will become polar, and the otherwise nonpolar molecules containing these functional groups become polar and so become soluble in some <a href="Aqueous_solution" title="Aqueous solution">aqueous</a> environment.

</p><p>Combining the names of functional groups with the names of the parent <a href="Alkane" title="Alkane">alkanes</a> generates what is termed a <a href="Systematic_name" title="Systematic name">systematic nomenclature</a> for naming <a href="Organic_compound" title="Organic compound">organic compounds</a>. In traditional nomenclature, the first carbon atom after the carbon that attaches to the functional group is called the <a href="Alpha_carbon" class="mw-redirect" title="Alpha carbon">alpha carbon</a>; the second, beta carbon, the third, gamma carbon, etc. If there is another functional group at a carbon, it may be named with the Greek letter, e.g., the gamma-amine in <a href="Gamma-aminobutyric_acid" class="mw-redirect" title="Gamma-aminobutyric acid">gamma-aminobutyric acid</a> is on the third carbon of the carbon chain attached to the carboxylic acid group. <a href="IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC conventions</a> call for numeric labeling of the position, e.g. 4-aminobutanoic acid. In traditional names various qualifiers are used to label <a href="Isomer" title="Isomer">isomers</a>, for example, isopropanol (IUPAC name: propan-2-ol) is an isomer of n-propanol (propan-1-ol). The term <a href="Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> has some overlap with the term "functional group". However, a moiety is an entire "half" of a molecule, which can be not only a single functional group, but also a larger unit consisting of multiple functional groups. For example, an "aryl moiety" may be any group containing an <a href="Aromaticity" title="Aromaticity">aromatic ring</a>, regardless of how many functional groups the said aryl has.

</p>

<div class="mw-heading mw-heading2"><h2 id="Table_of_common_functional_groups">Table of common functional groups</h2></div>

<p>The following is a list of common functional groups.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In the formulas, the symbols R and R' usually denote an attached hydrogen, or a <a href="Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> <a href="Side_chain" title="Side chain">side chain</a> of any length, but may sometimes refer to any group of atoms.

</p>

<div class="mw-heading mw-heading3"><h3 id="Hydrocarbons">Hydrocarbons</h3></div>

<p>Hydrocarbons are a class of molecule that is defined by functional groups called <a href="https://en.wiktionary.org/wiki/hydrocarbyl" class="extiw external" title="wikt:hydrocarbyl">hydrocarbyls</a> 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>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Alkane" title="Alkane">Alkane</a></td>

<td><a href="Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a>

</td>

<td>R(CH<sub>2</sub>)<sub>n</sub>H

</td>

</td>

<td>alkyl-</td>

<td>-ane

</td>

<td><span typeof="mw:File"></span><br><a href="Ethane" title="Ethane">Ethane</a>

</td></tr>

<tr>

<td><a href="Alkene" title="Alkene">Alkene</a></td>

<td><a href="Alkene" title="Alkene">Alkenyl</a>

</td>

</td>

</td>

<td>alkenyl-</td>

<td>-ene

</td>

<td><span typeof="mw:File"></span><br><a href="Ethylene" title="Ethylene">Ethylene</a><br><i>(Ethene)</i>

</td></tr>

<tr>

<td><a href="Alkyne" title="Alkyne">Alkyne</a></td>

<td><a href="Alkyne" title="Alkyne">Alkynyl</a>

</td>

</td>

</mrow>

</mrow>

</mrow>

<msup>

</msup>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-C#C-R'}}}</annotation>

</semantics>

</math></span><img src="./662588089dc7d143d01ddaf9859adbf79a581652.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:12.886ex; height:2.676ex;" alt="{\displaystyle {\ce {R-C#C-R'}}}" loading="lazy"></span>

</td>

<td>alkynyl-</td>

<td>-yne

</td>

</mrow>

</mrow>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {H-C#C-H}}}</annotation>

</semantics>

</math></span><img src="./cf0917a0feb72dc66cdca7497c4f2683ea3839dd.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:12.267ex; height:2.343ex;" alt="{\displaystyle {\ce {H-C#C-H}}}" loading="lazy"></span><br><a href="Acetylene" title="Acetylene">Acetylene</a><br><i>(Ethyne)</i>

</td></tr>

<tr>

<td><a href="Benzene" title="Benzene">Benzene derivative</a>

</td>

<td><a href="Phenyl" class="mw-redirect" title="Phenyl">Phenyl</a>

</td>

<td>RC<sub>6</sub>H<sub>5</sub><br>RPh

</td>

</td>

<td>phenyl-</td>

<td>-benzene

</td>

<td><span typeof="mw:File"></span><br><a href="Cumene" title="Cumene">Cumene</a><br><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="Tert-butyl" class="mw-redirect" title="Tert-butyl">tert-butyl</a>, <a href="Bornyl" class="mw-redirect" title="Bornyl">bornyl</a>, <a href="Cyclohexyl" class="mw-redirect" title="Cyclohexyl">cyclohexyl</a>, etc. There are several functional groups that contain an alkene such as <a href="Vinyl_group" title="Vinyl group">vinyl group</a>, <a href="Allyl_group" title="Allyl group">allyl group</a>, or <a href="Acryl" class="mw-redirect" title="Acryl">acrylic group</a>. Hydrocarbons may form charged structures: positively charged <a href="Carbocation" title="Carbocation">carbocations</a> or negative <a href="Carbanion" title="Carbanion">carbanions</a>. Carbocations are often named <i>-um</i>. Examples are <a href="Tropylium" class="mw-redirect" title="Tropylium">tropylium</a> and <a href="Triphenylmethyl" class="mw-redirect" title="Triphenylmethyl">triphenylmethyl</a> cations and the <a href="Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a> anion.

</p>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_halogens">Groups containing halogens</h3></div>

<p><a href="Haloalkane" title="Haloalkane">Haloalkanes</a> are a class of molecule that is defined by a carbon–<a href="Halogen" title="Halogen">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="Fluorination" class="mw-redirect" title="Fluorination">fluorinated</a> compounds, haloalkanes readily undergo <a href="Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a> reactions or <a href="Elimination_reaction" title="Elimination reaction">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>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Haloalkane" title="Haloalkane">haloalkane</a></td>

</td>

<td>RX

</td>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-X}}}</annotation>

</semantics>

</math></span><img src="./3392d63277240fc2839c0b9cf3b729931308b3c5.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:5.262ex; height:2.343ex;" alt="{\displaystyle {\ce {R-X}}}" loading="lazy"></span>

</td>

<td>alkyl <b>halide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Chloroethane" title="Chloroethane">Chloroethane</a><br><i>(Ethyl chloride)</i>

</td></tr>

<tr>

<td><a href="Fluoroalkane" class="mw-redirect" title="Fluoroalkane">fluoroalkane</a></td>

<td><a href="Fluorine" title="Fluorine">fluoro</a>

</td>

<td>RF

</td>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-F}}}</annotation>

</semantics>

</math></span><img src="./b66849a62477b082b6cf030fa74bdfcce550e390.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:5.037ex; height:2.343ex;" alt="{\displaystyle {\ce {R-F}}}" loading="lazy"></span>

</td>

<td>fluoro-</td>

<td>alkyl <b>fluoride</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Fluoromethane" title="Fluoromethane">Fluoromethane</a><br><i>(Methyl fluoride)</i>

</td></tr>

<tr>

<td><a href="Chloroalkane" class="mw-redirect" title="Chloroalkane">chloroalkane</a></td>

<td><a href="Chlorine" title="Chlorine">chloro</a>

</td>

<td>RCl

</td>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-Cl}}}</annotation>

</semantics>

</math></span><img src="./36283f35bebe1b77a6c35e876417f966bbf22874.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:5.844ex; height:2.343ex;" alt="{\displaystyle {\ce {R-Cl}}}" loading="lazy"></span>

</td>

<td>chloro-</td>

<td>alkyl <b>chloride</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Chloromethane" title="Chloromethane">Chloromethane</a><br><i>(Methyl chloride)</i>

</td></tr>

<tr>

<td><a href="Bromoalkane" class="mw-redirect" title="Bromoalkane">bromoalkane</a></td>

<td><a href="Bromine" title="Bromine">bromo</a>

</td>

<td>RBr

</td>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-Br}}}</annotation>

</semantics>

</math></span><img src="./b0bb9d6d34e8988570f6527289e25ac8ef105eb7.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:6.076ex; height:2.343ex;" alt="{\displaystyle {\ce {R-Br}}}" loading="lazy"></span>

</td>

<td>bromo-</td>

<td>alkyl <b>bromide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Bromomethane" title="Bromomethane">Bromomethane</a><br><i>(Methyl bromide)</i>

</td></tr>

<tr>

<td><a href="Iodoalkane" class="mw-redirect" title="Iodoalkane">iodoalkane</a></td>

</td>

<td>RI

</td>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-I}}}</annotation>

</semantics>

</math></span><img src="./9560fc5df4017e8ded9843bd3b968a82c864ac91.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:4.358ex; height:2.343ex;" alt="{\displaystyle {\ce {R-I}}}" loading="lazy"></span>

</td>

<td>alkyl <b>iodide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Iodomethane" title="Iodomethane">Iodomethane</a><br><i>(Methyl iodide)</i>

</td></tr>

</tbody></table>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_oxygen">Groups containing oxygen</h3></div>

<p>Compounds that contain C–O bonds each possess differing reactivity based upon the location and <a href="Orbital_hybridisation" title="Orbital hybridisation">hybridization</a> of the C–O bond, owing to the electron-withdrawing effect of sp-hybridized oxygen (carbonyl groups) and the donating effects of sp<sup>2</sup>-hybridized oxygen (alcohol groups).

</p>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a>

</td>

<td><a href="Hydroxy" class="mw-disambig" title="Hydroxy">Hydroxy</a>

</td>

<td>ROH

</td>

<td>

</td>

<td>hydroxy-</td>

</td>

<td><span typeof="mw:File"></span><br><a href="Methanol" title="Methanol">Methanol</a>

</td></tr>

<tr>

<td><a href="Ketone" title="Ketone">Ketone</a></td>

<td><a href="Ketone" title="Ketone">Ketone</a>

</td>

<td>RCOR′

</td>

</td>

</td>

<td><span typeof="mw:File"></span><br><a href="Butanone" title="Butanone">Butanone</a><br><i>(Methyl ethyl ketone)</i>

</td></tr>

<tr>

<td><a href="Aldehyde" title="Aldehyde">Aldehyde</a></td>

<td><a href="Aldehyde" title="Aldehyde">Aldehyde</a>

</td>

<td>RCHO

</td>

</td>

<td>formyl- (-COH)<br>or<br>oxo- (=O)</td>

</td>

<td><span typeof="mw:File"></span><br><a href="Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a><br><i>(Ethanal)</i>

</td></tr>

<tr>

<td><a href="Acyl_halide" title="Acyl halide">Acyl halide</a></td>

<td>Haloformyl

</td>

<td>RCOX

</td>

</td>

<td>carbonofluoridoyl-<br>carbonochloridoyl-<br>carbonobromidoyl-<br>carbonoiodidoyl-</td>

<td>-oyl <b>fluoride</b><br> -oyl <b>chloride</b><br> -oyl <b>bromide</b><br> -oyl <b>iodide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Acetyl_chloride" title="Acetyl chloride">Acetyl chloride</a><br><i>(Ethanoyl chloride)</i>

</td></tr>

<tr>

<td><a href="Carbonate_ester" title="Carbonate ester">Carbonate</a>

</td>

<td><a href="Carbonate_ester" title="Carbonate ester">Carbonate ester</a>

</td>

<td>ROCOOR′

</td>

</td>

<td>(alkoxycarbonyl)oxy-

</td>

<td>alkyl <b>carbonate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Triphosgene" title="Triphosgene">Triphosgene</a><br><i>(bis(trichloromethyl) carbonate)</i>

</td></tr>

<tr>

<td><a href="Carboxylic_acid" title="Carboxylic acid">Carboxylate</a>

</td>

<td><a href="Carboxylate" title="Carboxylate">Carboxylate</a></td>

</td>

</td>

<td>carboxylato-</td>

<td>-oate

</td>

<td><span typeof="mw:File"></span><br><a href="Sodium_acetate" title="Sodium acetate">Sodium acetate</a><br><i>(Sodium ethanoate)</i>

</td></tr>

<tr>

<td><a href="Carboxylic_acid" title="Carboxylic acid">Carboxylic acid</a>

</td>

<td><a href="Carboxyl" class="mw-redirect" title="Carboxyl">Carboxyl</a></td>

<td>RCOOH

</td>

</td>

<td>carboxy-</td>

</td>

<td><span typeof="mw:File"></span><br><a href="Acetic_acid" title="Acetic acid">Acetic acid</a><br><i>(Ethanoic acid)</i>

</td></tr>

<tr>

<td><a href="Ester" title="Ester">Ester</a></td>

<td><a href="Ester" title="Ester">Carboalkoxy</a>

</td>

<td>RCOOR′

</td>

</td>

<td>alkanoyloxy-<br>or<br>alkoxycarbonyl

</td>

<td>alkyl alkan<b>oate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Ethyl_butyrate" title="Ethyl butyrate">Ethyl butyrate</a><br><i>(Ethyl butanoate)</i>

</td></tr>

<tr>

<td><a href="Organic_peroxide" class="mw-redirect" title="Organic peroxide">Hydroperoxide</a>

</td>

<td><a href="Organic_peroxide" class="mw-redirect" title="Organic peroxide">Hydroperoxy</a>

</td>

<td>ROOH

</td>

</td>

<td>hydroperoxy-

</td>

<td>alkyl <b>hydroperoxide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Tert-Butyl_hydroperoxide" title="Tert-Butyl hydroperoxide"><i>tert</i>-Butyl hydroperoxide</a>

</td></tr>

<tr>

<td><a href="Organic_peroxide" class="mw-redirect" title="Organic peroxide">Peroxide</a>

</td>

<td><a href="Organic_peroxide" class="mw-redirect" title="Organic peroxide">Peroxy</a>

</td>

<td>ROOR′

</td>

</td>

<td>peroxy-

</td>

<td>alkyl <b>peroxide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Di-tert-butyl_peroxide" title="Di-tert-butyl peroxide">Di-tert-butyl peroxide</a>

</td></tr>

<tr>

<td><a href="Ether" title="Ether">Ether</a></td>

<td><a href="Ether" title="Ether">Ether</a>

</td>

<td>ROR′

</td>

<td>

</td>

<td>alkoxy-

</td>

<td>alkyl <b>ether</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Diethyl_ether" title="Diethyl ether">Diethyl ether</a><br><i>(Ethoxyethane)</i>

</td></tr>

<tr>

<td><a href="Hemiacetal" title="Hemiacetal">Hemiacetal</a></td>

<td><a href="Hemiacetal" title="Hemiacetal">Hemiacetal</a>

</td>

<td>R<sub>2</sub>CH(OR<sub>1</sub>)(OH)

</td>

</td>

<td>alkoxy -ol

</td>

<td>-al alkyl <b>hemiacetal</b>

</td>

<td>

</td></tr>

<tr>

<td><a href="Hemiketal" class="mw-redirect" title="Hemiketal">Hemiketal</a></td>

<td><a href="Hemiketal" class="mw-redirect" title="Hemiketal">Hemiketal</a>

</td>

<td>RC(ORʺ)(OH)R′

</td>

</td>

<td>alkoxy -ol

</td>

<td>-one alkyl <b>hemiketal</b>

</td>

<td>

</td></tr>

<tr>

<td><a href="Acetal" title="Acetal">Acetal</a></td>

<td><a href="Acetal" title="Acetal">Acetal</a>

</td>

<td>RCH(OR′)(OR″)

</td>

</td>

<td>dialkoxy-

</td>

<td>-al dialkyl <b>acetal</b>

</td>

<td>

</td></tr>

<tr>

<td><a href="Ketal" class="mw-redirect" title="Ketal">Ketal</a> (or <a href="Acetal" title="Acetal">Acetal</a>)</td>

<td><a href="Ketal" class="mw-redirect" title="Ketal">Ketal</a> (or <a href="Acetal" title="Acetal">Acetal</a>)

</td>

</td>

</td>

<td>dialkoxy-

</td>

<td>-one dialkyl <b>ketal</b>

</td>

<td>

</td></tr>

<tr>

<td><a href="Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></td>

<td><a href="Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a>

</td>

</td>

</td>

<td>trialkoxy-

</td>

<td>

</td>

<td>

</td></tr>

<tr>

<td><a href="Heterocycle" class="mw-redirect" title="Heterocycle">Heterocycle</a><br> (if cyclic)</td>

<td><a href="Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a>

</td>

</td>

<td>

<p>

</p>

</td>

<td>methylenedioxy-

</td>

<td>-dioxole

</td>

<td><span typeof="mw:File"></span><br><a href="1%2C3-Benzodioxole" title="1,3-Benzodioxole">1,2-Methylenedioxybenzene</a><br><i>(1,3-Benzodioxole)</i>

</td></tr>

<tr>

<td><a href="Orthocarbonate_ester" class="mw-redirect" title="Orthocarbonate ester">Orthocarbonate ester</a></td>

<td><a href="Orthocarbonate_ester" class="mw-redirect" title="Orthocarbonate ester">Orthocarbonate ester</a>

</td>

</td>

</td>

<td>tetralkoxy-

</td>

<td><i>tetraalkyl</i> <b>orthocarbonate</b>

</td>

<td><span class="mw-default-size" typeof="mw:File"></span><br><a href="Tetramethoxymethane" title="Tetramethoxymethane">Tetramethoxymethane</a>

</td></tr>

<tr>

<td><a href="Organic_acid_anhydride" title="Organic acid anhydride">Organic acid anhydride</a></td>

<td><a href="Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Carboxylic anhydride</a>

</td>

</td>

</td>

<td>

</td>

<td>anhydride

</td>

<td><span typeof="mw:File"></span><br><a href="Butyric_anhydride" title="Butyric anhydride">Butyric anhydride</a>

</td></tr></tbody></table>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_nitrogen">Groups containing nitrogen</h3></div>

<p>Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of <a href="Amide" title="Amide">amides</a>.

</p>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Amide" title="Amide">Amide</a></td>

<td><a href="Carboxamide" class="mw-redirect" title="Carboxamide">Carboxamide</a>

</td>

<td>RCONR'R"

</td>

</td>

<td>carboxamido-<br>or<br>carbamoyl-</td>

<td>-amide

</td>

<td><span typeof="mw:File"></span><br><a href="Acetamide" title="Acetamide">Acetamide</a><br><i>(Ethanamide)</i>

</td></tr>

<tr>

<td><a href="Amidine" title="Amidine">Amidine</a>

</td>

<td><a href="Amidine" title="Amidine">Amidine</a>

</td>

<td>R<sub>4</sub>C(NR<sub>1</sub>)(NR<sub>2</sub>R<sub>3</sub>)

</td>

<td>

</td>

<td>amidino-

</td>

<td>-amidine

</td>

<td>acetamidine

<p>(acetimidamide)

</p>

</td></tr>

<tr>

<td><a href="Guanidine" title="Guanidine">Guanidine</a>

</td>

<td><a href="Guanidine" title="Guanidine">Guanidine</a>

</td>

<td>RNC(NR<sub>2</sub>)<sub>2</sub>)

</td>

<td>

</td>

<td>Guanidin-

</td>

<td>-Guanidine

</td>

<td><br><a href="Guanidinopropionic_acid" title="Guanidinopropionic acid">Guanidinopropionic acid</a>

</td></tr>

<tr>

<td rowspan="5"><a href="Amine" title="Amine">Amines</a>

</td>

<td><a href="Amine" title="Amine">Primary amine</a>

</td>

</td>

</td>

<td>amino-</td>

<td>-amine

</td>

<td><span typeof="mw:File"></span><br><a href="Methylamine" title="Methylamine">Methylamine</a><br><i>(Methanamine)</i>

</td></tr>

<tr>

<td><a href="Amine" title="Amine">Secondary amine</a>

</td>

<td>R'R"NH

</td>

</td>

<td>amino-</td>

<td>-amine

</td>

<td><span typeof="mw:File"></span><br><a href="Dimethylamine" title="Dimethylamine">Dimethylamine</a>

</td></tr>

<tr>

<td><a href="Amine" title="Amine">Tertiary amine</a>

</td>

<td>R<sub>3</sub>N

</td>

</td>

<td>amino-</td>

<td>-amine

</td>

<td><span typeof="mw:File"></span><br><a href="Trimethylamine" title="Trimethylamine">Trimethylamine</a>

</td></tr>

<tr>

<td><a href="Quaternary_ammonium_cation" title="Quaternary ammonium cation">4° ammonium ion</a>

</td>

</td>

</td>

<td>ammonio-</td>

<td>-ammonium

</td>

<td><span typeof="mw:File"></span><br><a href="Choline" title="Choline">Choline</a>

</td></tr>

<tr>

<td><a href="Hydrazone" title="Hydrazone">Hydrazone</a>

</td>

</td>

</td>

<td>hydrazino-

</td>

<td>-hydrazine

</td>

<td><span typeof="mw:File"></span><br><a href="Benzophenone" title="Benzophenone">Benzophenone</a>

</td></tr>

<tr>

<td rowspan="4"><a href="Imine" title="Imine">Imine</a>

</td>

<td><a href="Imine" title="Imine">Primary ketimine</a>

</td>

<td>RC(=NH)R'

</td>

</td>

<td>imino-</td>

<td>-imine

</td>

<td>

</td></tr>

<tr>

<td><a href="Imine" title="Imine">Secondary ketimine</a>

</td>

</td>

</td>

<td>imino-</td>

<td>-imine

</td>

<td>

</td></tr>

<tr>

<td><a href="Imine" title="Imine">Primary aldimine</a>

</td>

<td>RC(=NH)H

</td>

</td>

<td>imino-</td>

<td>-imine

</td>

<td><span typeof="mw:File"></span><br><a href="Ethanimine" title="Ethanimine">Ethanimine</a>

</td></tr>

<tr>

<td><a href="Imine" title="Imine">Secondary aldimine</a>

</td>

<td>RC(=NR')H

</td>

</td>

<td>imino-</td>

<td>-imine

</td>

<td>

</td></tr>

<tr>

<td><a href="Imide" title="Imide">Imide</a></td>

<td><a href="Imide" title="Imide">Imide</a>

</td>

<td>(RCO)<sub>2</sub>NR'

</td>

</td>

<td>imido-

</td>

<td>-imide

</td>

<td><span typeof="mw:File"></span><br><a href="Succinimide" title="Succinimide">Succinimide</a><br>(Pyrrolidine-2,5-dione)

</td></tr>

<tr>

<td><a href="Azide" title="Azide">Azide</a>

</td>

<td><a href="Azide" title="Azide">Azide</a>

</td>

</td>

</td>

<td>azido-</td>

<td>alkyl <b>azide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Phenyl_azide" title="Phenyl azide">Phenyl azide</a><br>(Azidobenzene)

</td></tr>

<tr>

<td><a href="Azo_compound" title="Azo compound">Azo compound</a>

</td>

<td><a href="Azo_compound" title="Azo compound">Azo<br>(Diimide)</a>

</td>

<td>RN<sub>2</sub>R'

</td>

</td>

<td>-diazene

</td>

<td><span typeof="mw:File"></span><br><a href="Methyl_orange" title="Methyl orange">Methyl orange</a><br>(p-dimethylamino-azobenzenesulfonic acid)

</td></tr>

<tr>

<td rowspan="2"><a href="Cyanate" title="Cyanate">Cyanates</a>

</td>

<td><a href="Cyanate" title="Cyanate">Cyanate</a></td>

<td>ROCN

</td>

</td>

<td>cyanato-

</td>

<td>alkyl <b>cyanate</b>

</td>

<td><span typeof="mw:File"></span><br>Methyl cyanate

</td></tr>

<tr>

<td><a href="Isocyanate" title="Isocyanate">Isocyanate</a></td>

<td>RNCO

</td>

</td>

<td>isocyanato-

</td>

<td>alkyl <b>isocyanate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a>

</td></tr>

<tr>

<td><a href="Nitrate" title="Nitrate">Nitrate</a></td>

<td><a href="Nitrate" title="Nitrate">Nitrate</a>

</td>

</td>

</td>

<td>nitrooxy-, nitroxy-</td>

<td>

<p>alkyl <b>nitrate</b>

</p>

</td>

<td><span typeof="mw:File"></span><br><a href="Amyl_nitrate" title="Amyl nitrate">Amyl nitrate</a><br><i>(1-nitrooxypentane)</i>

</td></tr>

<tr>

<td rowspan="2"><a href="Nitrile" title="Nitrile">Nitrile</a>

</td>

<td><a href="Nitrile" title="Nitrile">Nitrile</a>

</td>

<td>RCN

</td>

</mrow>

</mrow>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {R-\!#N}}}</annotation>

</semantics>

</math></span><img src="./0def1ceb9ee02344feaeeca3d84da69f9b601903.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:6.683ex; height:2.343ex;" alt="{\displaystyle {\ce {R-\!#N}}}" loading="lazy"></span>

</td>

<td>cyano-

</td>

<td>alkane<b>nitrile</b><br>alkyl <b>cyanide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Benzonitrile" title="Benzonitrile">Benzonitrile</a><br><i>(Phenyl cyanide)</i>

</td></tr>

<tr>

<td><a href="Isonitrile" class="mw-redirect" title="Isonitrile">Isonitrile</a></td>

<td>RNC

</td>

</td>

<td>isocyano-

</td>

<td>alkane<b>isonitrile</b><br>alkyl <b>isocyanide</b>

</td>

</mrow>

</mrow>

</msubsup>

</mrow>

</mrow>

<mover>

</mrow>

</mover>

</mrow>

</mrow>

<msup>

</mrow>

</msup>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {H3C}}{-}{\overset {+}{{\ce {N}}}}{\ce {#C^-}}}</annotation>

</semantics>

</math></span><img src="./318b166027c3f5d010e17a4d7a67e3507f9841ef.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:13.024ex; height:4.509ex;" alt="{\displaystyle {\ce {H3C}}{-}{\overset {+}{{\ce {N}}}}{\ce {#C^-}}}" loading="lazy"></span><br><a href="Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a>

</td></tr>

<tr>

<td><a href="Alkyl_nitrites" class="mw-redirect" title="Alkyl nitrites">Nitrite</a></td>

<td><a href="Alkyl_nitrites" class="mw-redirect" title="Alkyl nitrites">Nitrosooxy</a>

</td>

<td>RONO

</td>

</td>

<td>nitrosooxy-</td>

<td>

<p>alkyl <b>nitrite</b>

</p>

</td>

<td><span typeof="mw:File"></span><br><a href="Isoamyl_nitrite" class="mw-redirect" title="Isoamyl nitrite">Isoamyl nitrite</a><br><i>(3-methyl-1-nitrosooxybutane)</i>

</td></tr>

<tr>

<td><a href="Nitro_compound" title="Nitro compound">Nitro compound</a>

</td>

<td><a href="Nitro_functional_group" class="mw-redirect" title="Nitro functional group">Nitro</a>

</td>

</td>

</td>

<td>nitro-</td>

<td> 

</td>

<td><span typeof="mw:File"></span><br><a href="Nitromethane" title="Nitromethane">Nitromethane</a>

</td></tr>

<tr>

<td><a href="Nitroso" title="Nitroso">Nitroso compound</a>

</td>

<td><a href="Nitroso" title="Nitroso">Nitroso</a></td>

<td>RNO

</td>

</td>

<td>nitroso- (Nitrosyl-)</td>

<td> 

</td>

<td><span typeof="mw:File"></span><br><a href="Nitrosobenzene" title="Nitrosobenzene">Nitrosobenzene</a>

</td></tr>

<tr>

<td><a href="Oxime" title="Oxime">Oxime</a>

</td>

<td><a href="Oxime" title="Oxime">Oxime</a></td>

<td>RCH=NOH

</td>

</td>

<td><a href="Oxime" title="Oxime">Oxime</a>

</td>

<td><span typeof="mw:File"></span><br><a href="Acetone_oxime" title="Acetone oxime">Acetone oxime</a><br><i>(2-Propanone oxime)</i>

</td></tr>

<tr>

<td><a href="Pyridine" title="Pyridine">Pyridine derivative</a>

</td>

<td><a href="Pyridine" title="Pyridine">Pyridyl</a>

</td>

<td>RC<sub>5</sub>H<sub>4</sub>N

</td>

<td>

</p>

</td>

<td>

<p>4-pyridyl<br>(pyridin-4-yl)

</p><p>3-pyridyl<br>(pyridin-3-yl)

</p><p>2-pyridyl<br>(pyridin-2-yl)

</p>

</td>

<td>-pyridine

</td>

<td><span typeof="mw:File"></span><br><a href="Nicotine" title="Nicotine">Nicotine</a>

</td></tr>

<tr>

<td><a href="Carbamate" title="Carbamate">Carbamate ester</a>

</td>

<td><a href="Carbamate" title="Carbamate">Carbamate</a></td>

</td>

</td>

<td>(-carbamoyl)oxy-</td>

<td>-carbamate

</td>

<td><span typeof="mw:File"></span><br><a href="Chlorpropham" title="Chlorpropham">Chlorpropham</a><br><i>(Isopropyl (3-chlorophenyl)carbamate)</i>

</td></tr>

</tbody></table>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_sulfur">Groups containing sulfur</h3></div>

<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>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Thiol" title="Thiol">Thiol</a>

</td>

<td><a href="Thiol" title="Thiol">Sulfhydryl</a>

</td>

<td>RSH

</td>

</td>

<td>sulfanyl-<br>(-SH)

</td>

<td>-<b>thiol</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Ethanethiol" title="Ethanethiol">Ethanethiol</a>

</td></tr>

<tr>

<td><a href="Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a><br>(<a href="Thioether" class="mw-redirect" title="Thioether">Thioether</a>)

</td>

<td><a href="Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a>

</td>

<td>RSR'

</td>

</td>

<td><i>substituent</i> sulfanyl-<br>(-SR')

</td>

<td>di(<i>substituent</i>) <b>sulfide</b>

</td>

<td><br><span typeof="mw:File"></span><br><br><a href="(Methylsulfanyl)methane" class="mw-redirect" title="(Methylsulfanyl)methane">(Methylsulfanyl)methane</a> (prefix) or<br><a href="Dimethyl_sulfide" title="Dimethyl sulfide">Dimethyl sulfide</a> (suffix)

</td></tr>

<tr>

<td><a href="Disulfide_bond" class="mw-redirect" title="Disulfide bond">Disulfide</a></td>

<td><a href="Disulfide" title="Disulfide">Disulfide</a>

</td>

<td>RSSR'

</td>

</td>

<td><i>substituent</i> disulfanyl-<br>(-SSR')

</td>

<td>di(<i>substituent</i>) <b>disulfide</b>

</td>

<td><br><span typeof="mw:File"></span><br><br><a href="(Methyldisulfanyl)methane" class="mw-redirect" title="(Methyldisulfanyl)methane">(Methyldisulfanyl)methane</a> (prefix) or<br><a href="Dimethyl_disulfide" title="Dimethyl disulfide">Dimethyl disulfide</a> (suffix)

</td></tr>

<tr>

<td><a href="Sulfoxide" title="Sulfoxide">Sulfoxide</a>

</td>

<td><a href="Sulfoxide" title="Sulfoxide">Sulfinyl</a>

</td>

<td>RSOR'

</td>

</td>

<td>-sulfinyl-<br>(-SOR')

</td>

<td>di(<i>substituent</i>) <b>sulfoxide</b>

</td>

<td><span typeof="mw:File"></span><br><a href="(Methanesulfinyl)methane" class="mw-redirect" title="(Methanesulfinyl)methane">(Methanesulfinyl)methane</a> (prefix) or<br><a href="Dimethyl_sulfoxide" title="Dimethyl sulfoxide">Dimethyl sulfoxide</a> (suffix)

</td></tr>

<tr>

<td><a href="Sulfone" title="Sulfone">Sulfone</a>

</td>

<td><a href="Sulfone" title="Sulfone">Sulfonyl</a>

</td>

<td>RSO<sub>2</sub>R'

</td>

</td>

<td>-sulfonyl-<br>(-SO<sub>2</sub>R')

</td>

<td>di(<i>substituent</i>) <b>sulfone</b>

</td>

<td><span typeof="mw:File"></span><br><a href="(Methanesulfonyl)methane" class="mw-redirect" title="(Methanesulfonyl)methane">(Methanesulfonyl)methane</a> (prefix) or<br><a href="Dimethyl_sulfone" class="mw-redirect" title="Dimethyl sulfone">Dimethyl sulfone</a> (suffix)

</td></tr>

<tr>

<td><a href="Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></td>

<td>Sulfino

</td>

<td>RSO<sub>2</sub>H

</td>

</td>

<td>sulfino-<br>(-SO<sub>2</sub>H)

</td>

<td>-<b>sulfinic acid</b>

</td>

<td><span typeof="mw:File"></span><br><a href="2-Aminoethanesulfinic_acid" class="mw-redirect" title="2-Aminoethanesulfinic acid">2-Aminoethanesulfinic acid</a>

</td></tr>

<tr>

<td><a href="Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></td>

<td>Sulfo

</td>

<td>RSO<sub>3</sub>H

</td>

</td>

<td>sulfo-<br>(-SO<sub>3</sub>H)

</td>

<td>-<b>sulfonic acid</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Benzenesulfonic_acid" title="Benzenesulfonic acid">Benzenesulfonic acid</a>

</td></tr>

<tr>

<td><a href="Sulfonate_ester" class="mw-redirect" title="Sulfonate ester">Sulfonate ester</a></td>

<td>Sulfo

</td>

<td>RSO<sub>3</sub>R'

</td>

</td>

<td>(-sulfonyl)oxy-<br>or<br>alkoxysulfonyl-

</td>

<td><i>R'</i> <i>R</i>-<b>sulfonate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Methyl_trifluoromethanesulfonate" title="Methyl trifluoromethanesulfonate">Methyl trifluoromethanesulfonate</a> or<br>Methoxysulfonyl trifluoromethane (prefix)

</td></tr>

<tr>

<td rowspan="2"><a href="Thiocyanate" title="Thiocyanate">Thiocyanate</a>

</td>

<td><a href="Thiocyanate" title="Thiocyanate">Thiocyanate</a></td>

<td>RSCN

</td>

</td>

<td>thiocyanato-<br>(-SCN)

</td>

<td><i>substituent</i> <b>thiocyanate</b>

</td>

<td><span typeof="mw:File"></span><br>Phenyl thiocyanate

</td></tr>

<tr>

<td><a href="Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></td>

<td>RNCS

</td>

</td>

<td>isothiocyanato-<br>(-NCS)

</td>

<td><i>substituent</i> <b>isothiocyanate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a>

</td></tr>

<tr>

<td><a href="Thioketone" title="Thioketone">Thioketone</a>

</td>

<td><a href="Carbonothioyl" class="mw-redirect" title="Carbonothioyl">Carbonothioyl</a>

</td>

<td>RCSR'

</td>

</td>

<td>-thioyl-<br>(-CSR')<br>or<br>sulfanylidene-<br>(=S)

</td>

<td>-<b>thione</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Diphenylmethanethione" class="mw-redirect" title="Diphenylmethanethione">Diphenylmethanethione</a><br>(<a href="Thiobenzophenone" title="Thiobenzophenone">Thiobenzophenone</a>)

</td></tr>

<tr>

<td><a href="Thial" title="Thial">Thial</a>

</td>

<td><a href="Carbonothioyl" class="mw-redirect" title="Carbonothioyl">Carbonothioyl</a>

</td>

<td>RCSH

</td>

</td>

<td>methanethioyl-<br>(-CSH)<br>or<br>sulfanylidene-<br>(=S)

</td>

<td>-<b>thial</b>

</td>

<td>

</td></tr>

<tr>

<td rowspan="2"><a href="Thiocarboxylic_acid" title="Thiocarboxylic acid">Thiocarboxylic acid</a>

</td>

<td>Carbothioic <i>S</i>-acid

</td>

<td>RC=OSH

</td>

<td>

</td>

<td>mercaptocarbonyl-

</td>

<td>-<b>thioic</b> <i>S</i>-<b>acid</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Thiobenzoic_acid" title="Thiobenzoic acid">Thiobenzoic acid</a><br><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>-<b>thioic</b> <i>O</i>-<b>acid</b>

</td>

<td>

</td></tr>

<tr>

<td rowspan="2"><a href="Thioester" title="Thioester">Thioester</a>

</td>

<td>Thiolester

</td>

<td>RC=OSR'

</td>

</td>

<td>

</td>

<td><i>S</i>-alkyl-alkane-<b>thioate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="S-Methyl_thioacrylate" title="S-Methyl thioacrylate">S-Methyl thioacrylate</a><br><i>(</i>S<i>-Methyl prop-2-enethioate)</i>

</td></tr>

<tr>

<td>Thionoester

</td>

<td>RC=SOR'

</td>

</td>

<td>

</td>

<td><i>O</i>-alkyl-alkane-<b>thioate</b>

</td>

<td>

</td></tr>

<tr>

<td><a href="Thiocarboxylic_acid#Dithiocarboxylic_acids" title="Thiocarboxylic acid">Dithiocarboxylic acid</a>

</td>

<td>Carbodithioic acid

</td>

<td>RCS<sub>2</sub>H

</td>

<td>

</td>

<td>dithiocarboxy-

</td>

<td>-<b>dithioic acid</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Dithiobenzoic_acid" title="Dithiobenzoic acid">Dithiobenzoic acid</a><br><i>(Benzenecarbodithioic acid)</i>

</td></tr>

<tr>

<td>Dithiocarboxylic acid ester

</td>

<td>Carbodithio

</td>

<td>RC=SSR'

</td>

</td>

<td>

</td>

<td>-<b>dithioate</b>

</td>

<td>

</td></tr></tbody></table>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_phosphorus">Groups containing phosphorus</h3></div>

<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>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Phosphine" title="Phosphine">Phosphine</a><br>(<a href="Phosphane" class="mw-redirect" title="Phosphane">Phosphane</a>)</td>

<td>Phosphino

</td>

<td>R<sub>3</sub>P

</td>

</td>

<td>phosphanyl-</td>

<td>-phosphane

</td>

<td><span typeof="mw:File"></span><br>Methylpropylphosphane

</td></tr>

<tr>

<td><a href="Phosphonic_acid" class="mw-redirect" title="Phosphonic acid">Phosphonic acid</a>

</td>

<td>Phosphono

</td>

</mrow>

</mrow>

</mrow>

</mrow>

</mrow>

</msubsup>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {RP(=O)(OH)2}}}</annotation>

</semantics>

</math></span><img src="./7230c377b4b1d3072590da6c411ff3b1ad6e8e12.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:15.134ex; height:3.009ex;" alt="{\displaystyle {\ce {RP(=O)(OH)2}}}" loading="lazy"></span>

</td>

</td>

<td>phosphono-

</td>

<td><i>substituent</i> <b>phosphonic acid</b>

</td>

<td><span typeof="mw:File"></span><br>Benzylphosphonic acid

</td></tr>

<tr>

<td rowspan="2"><a href="Phosphate" title="Phosphate">Phosphate</a>

</td>

<td rowspan="2">Phosphate

</td>

</mrow>

</mrow>

</mrow>

</mrow>

</mrow>

</msubsup>

</mrow>

</mstyle>

</mrow>

<annotation encoding="application/x-tex">{\displaystyle {\ce {ROP(=O)(OH)2}}}</annotation>

</semantics>

</math></span><img src="./c7f9fc53414b91c85b244fcd4a1f3cf95ab2c23c.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:16.942ex; height:3.009ex;" alt="{\displaystyle {\ce {ROP(=O)(OH)2}}}" loading="lazy"></span>

</td>

</td>

<td rowspan="2">phosphonooxy-<br>or<br><i>O</i>-phosphono- (phospho-)

</td>

<td rowspan="2"><i>substituent</i> <b>phosphate</b>

</td>

<td><span typeof="mw:File"></span><br><a href="Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a> (suffix)

</td></tr>

<tr>

<td><span typeof="mw:File"></span><br><i>O</i>-Phosphonocholine (prefix)<br>(<a href="Phosphocholine" title="Phosphocholine">Phosphocholine</a>)

</td></tr>

<tr>

<td rowspan="2"><a href="Phosphodiester_bonds" class="mw-redirect" title="Phosphodiester bonds">Phosphodiester</a>

</td>

<td rowspan="2"><a href="Phosphate" title="Phosphate">Phosphate</a>

</td>

</td>

</td>

<td rowspan="2"><small>[(alkoxy)hydroxyphosphoryl]oxy-<br>or<br><i>O</i>-[(alkoxy)hydroxyphosphoryl]-</small>

</td>

<td rowspan="2">di(<i>substituent</i>) hydrogen <b>phosphate</b><br>or<br>phosphoric acid di(<i>substituent</i>) <b>ester</b>

</td>

</td></tr>

<tr>

<td><small><i>O</i>‑[(2‑Guanidinoethoxy)hydroxyphosphoryl]‑<style data-mw-deduplicate="TemplateStyles:r920966791">

/* start https://en.wikipedia.org/ */

.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}

/* end https://en.wikipedia.org/ */

</style><span class="smallcaps">l</span>‑serine</small> (prefix)<br>(<a href="Lombricine" title="Lombricine">Lombricine</a>)

</td></tr></tbody></table>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_boron">Groups containing boron</h3></div>

<p>Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as <a href="Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a>.

</p>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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="Boronic_acid" title="Boronic acid">Boronic acid</a></td>

<td>Borono</td>

<td>Borono-</td>

<td><i>substituent</i><br><b>boronic acid</b></td>

<td><div class="center"><span typeof="mw:File"></span><br><a href="Phenylboronic_acid" title="Phenylboronic acid">Phenylboronic acid</a></div>

</td></tr>

<tr>

<td><a href="Boronic_acid#Boronic_esters_(also_named_boronate_esters)" title="Boronic acid">Boronic ester</a></td>

<td>Boronate</td>

<td>O-[bis(alkoxy)alkylboronyl]-</td>

<td><i>substituent</i><br><b>boronic acid</b><br>di(<i>substituent</i>) <b>ester</b></td>

<td>

</td></tr>

<tr>

<td><a href="Borinic_acid" title="Borinic acid">Borinic acid</a></td>

<td>Borino</td>

<td>Hydroxyborino-</td>

<td>di(<i>substituent</i>)<br><b>borinic acid</b></td>

<td>

</td></tr>

<tr>

<td><a href="Boronic_acid#Borinic_acids_and_esters" title="Boronic acid">Borinic ester</a></td>

<td>Borinate</td>

<td>O-[alkoxydialkylboronyl]-</td>

<td>di(<i>substituent</i>)<br><b>borinic acid</b><br><i>substituent</i> <b>ester</b></td>

<td><div class="center"><span typeof="mw:File"></span><br><small>Diphenylborinic acid 2-aminoethyl ester</small><br>(<a href="2-Aminoethoxydiphenyl_borate" title="2-Aminoethoxydiphenyl borate">2-Aminoethoxydiphenyl borate</a>)</div>

</td></tr></tbody></table>

<div class="mw-heading mw-heading3"><h3 id="Groups_containing_metals">Groups containing metals</h3></div>

</caption>

<th>Chemical class

</th>

<th>Structural formula

</th>

<th>Prefix

</th>

<th>Suffix

</th>

<th>Example

</th></tr>

<tr>

<td><a href="Organolithium_reagent" title="Organolithium reagent">Alkyllithium</a>

</td>

<td>RLi

</td>

<td rowspan="4">(tri/di)alkyl-

</td>

<td>-lithium

</td>

<p><a href="Methyllithium" title="Methyllithium">methyllithium</a>

</p>

</td></tr>

<tr>

<td><a href="Grignard_reagent" title="Grignard reagent">Alkylmagnesium halide</a>

</td>

/* start https://en.wikipedia.org/ */

.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}

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</style><sup class="citation nobold" id="ref_halogennote_1"><a href="#endnote_halogennote_1">[note 1]</a></sup>

</td>

<td>-magnesium halide

</td>

<p><a href="Methylmagnesium_chloride" title="Methylmagnesium chloride">methylmagnesium chloride</a>

</p>

</td></tr>

<tr>

<td>Alkylaluminium

</td>

</td>

<td>-aluminium

</td>

<p><a href="Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a>

</p>

</td></tr>

<tr>

<td><a href="Silyl_ether" title="Silyl ether">Silyl ether</a>

</td>

<td>R<sub>3</sub>SiOR

</td>

<td>-silyl ether

</td>

<p><a href="Trimethylsilyl_trifluoromethanesulfonate" title="Trimethylsilyl trifluoromethanesulfonate">trimethylsilyl triflate</a>

</p>

</td></tr></tbody></table>

<p><span class="citation wikicite" id="endnote_halogennote_1"><a href="#ref_halogennote_1"><b><sup>note 1</sup></b></a></span> <a href="Fluorine" title="Fluorine">Fluorine</a> is too electronegative to be bonded to magnesium; it becomes an <a href="Salt_(chemistry)" title="Salt (chemistry)">ionic salt</a> instead.

</p>

<div class="mw-heading mw-heading3"><h3 id="Names_of_radicals_or_moieties">Names of radicals or moieties</h3></div>

<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="Ethyne" class="mw-redirect" title="Ethyne">ethyne</a>" becomes "<a href="Ethynyl" class="mw-redirect" title="Ethynyl">ethynyl</a>").<sup id="cite_ref-qmul_4-0" class="reference"><a href="#cite_note-qmul-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p><p>When used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a <a href="Methylene_bridge" title="Methylene bridge">methylene bridge</a> (methanediyl) has two single bonds, whereas a <a href="Methylidene_group" class="mw-redirect" title="Methylidene group">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="Methylene_group" title="Methylene group">methylene</a> for methanediyl, 1,x-<a href="Phenylene" class="mw-redirect" title="Phenylene">phenylene</a> for phenyl-1,x-diyl (where x is 2, 3, or 4),<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="Carbyne" title="Carbyne">carbyne</a> for methylidyne, and <a href="Trityl" class="mw-redirect" title="Trityl">trityl</a> for triphenylmethyl.

</p>

<th><a href="Chemical_class" class="mw-redirect" title="Chemical class">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><div class="center"><a href="Methyl_group" title="Methyl group">Methyl group</a><br><a href="Methyl_radical" title="Methyl radical">Methyl radical</a></div>

</td></tr>

<tr>

<td>Double bond</td>

<td>-ylidene</td>

<td><div class="center"><a href="Methylidene" class="mw-redirect" title="Methylidene">Methylidene</a></div>

</td></tr>

<tr>

<td>Triple bond</td>

<td>-ylidyne</td>

<td><div class="center"><a href="Methylidyne" class="mw-redirect" title="Methylidyne">Methylidyne</a></div>

</td></tr>

<tr>

<td>Carboxylic <a href="Acyl" class="mw-redirect" title="Acyl">acyl</a> radical</td>

<td><div class="center"><a href="Acetyl" class="mw-redirect" title="Acetyl">Acetyl</a></div>

</td></tr></tbody></table>

<ul><li>Category:Functional groups</li>

<li><a href="Group_contribution_method" class="mw-redirect" title="Group contribution method">Group contribution method</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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</style><div class="reflist">

<li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="Compendium_of_Chemical_Terminology" class="mw-redirect" title="Compendium of Chemical Terminology">Compendium of Chemical Terminology</a> (IUPAC "Gold Book") <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/html/F/F02555.html">functional group</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190516163117/http://goldbook.iupac.org/html/F/F02555.html">Archived</a> 2019-05-16 at the <a href="Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span>

</li>

/* start https://en.wikipedia.org/ */

.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("./mw/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("./mw/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("./mw/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("./mw/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}

/* end https://en.wikipedia.org/ */

</style><cite id="CITEREFMarch1985" class="citation book cs1"><a href="Jerry_March" title="Jerry March">March, Jerry</a> (1985). <a rel="nofollow" class="external text" href="https://www.google.co.in/books/edition/_/ZKqWAQAACAAJ?hl=en"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (3rd ed.). New York: Wiley. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9780471854722</bdi>. <a href="OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/642506595">642506595</a>.</cite></span>

</li>

<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite id="CITEREFBrown2002" class="citation book cs1">Brown, Theodore (2002). <i>Chemistry: the central science</i>. Upper Saddle River, NJ: Prentice Hall. p. 1001. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0130669970</bdi>.</cite></span>

</li>

<li id="cite_note-qmul-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-qmul_4-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFMossW.H._Powell" class="citation web cs1">Moss, G. P.; W.H. Powell. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150209155729/http://www.chem.qmul.ac.uk/iupac/ions/RC811.html">"RC-81.1.1. Monovalent radical centers in saturated acyclic and monocyclic hydrocarbons, and the mononuclear EH4 parent hydrides of the carbon family"</a>. <i>IUPAC Recommendations 1993</i>. Department of Chemistry, <a href="Queen_Mary_University_of_London" title="Queen Mary University of London">Queen Mary University of London</a>. Archived from <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/ions/RC811.html#p11">the original</a> on 9 February 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">25 February</span> 2015</span>.</cite></span>

</li>

<li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.acdlabs.com/iupac/nomenclature/93/r93_271.htm">"R-2. 5 Substituent Prefix Names Derived from Parent Hydrides"</a>. IUPAC. 1993. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190322061930/https://www.acdlabs.com/iupac/nomenclature/93/r93_271.htm">Archived</a> from the original on 2019-03-22<span class="reference-accessdate">. Retrieved <span class="nowrap">2018-12-15</span></span>.</cite> section P-56.2.1</span>

</li>

<li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20170611171918/http://www.chem.qmul.ac.uk/iupac/ions/RC813.html">"Revised Nomenclature for Radicals, Ions, Radical Ions and Related Species (IUPAC Recommendations 1993: RC-81.3. Multiple radical centers)"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/ions/RC813.html">the original</a> on 2017-06-11<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-12-02</span></span>.</cite></span>

</li>

</ol></div></div>

<div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2></div>

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<div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Functional_groups" class="extiw external" title="commons:Functional groups"><span style="font-style:italic; font-weight:bold;">Functional groups</span></a>.</div></div>

</div>

<ul><li><a rel="nofollow" class="external text" href="https://www.acdlabs.com/iupac/nomenclature/">IUPAC Blue Book (organic nomenclature)</a></li>

<li><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070927121055/http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf">"IUPAC ligand abbreviations"</a> <span class="cs1-format">(PDF)</span>. <a href="IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>. 2 April 2004. Archived from <a rel="nofollow" class="external text" href="http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/TableVII-3.04.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 27 September 2007<span class="reference-accessdate">. Retrieved <span class="nowrap">25 February</span> 2015</span>.</cite></li>

<li><a rel="nofollow" class="external text" href="https://www.pearson.com/channels/organic-chemistry/learn/johnny/molecular-representations/functional-groups">Functional group video</a></li></ul>

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</style><div id="Functional_groups729" style="font-size:114%;margin:0 4em"></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a>

<ul><li><a href="Methyl_group" title="Methyl group">Methyl</a></li>

<li><a href="Ethyl_group" title="Ethyl group">Ethyl</a></li>

<li><a href="Propyl_group" title="Propyl group">Propyl</a></li>

<li><a href="Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li>

<li><a href="Butyl_group" title="Butyl group">Butyl</a></li>

<li><a href="Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li>

<li><a href="Methylene_group" title="Methylene group">Methylene</a>

<ul><li><a href="Methylene_bridge" title="Methylene bridge">Bridge</a></li>

<li><a href="Methine_group" title="Methine group">Methine</a></li></ul></li>

<li><a href="Alkene" title="Alkene">Alkene</a>

<ul><li><a href="Vinyl_group" title="Vinyl group">Vinyl</a></li>

<li><a href="Allyl_group" title="Allyl group">Allyl</a></li>

<li><a href="Propenyl" title="Propenyl">1-Propenyl</a></li>

<li><a href="Crotyl_group" title="Crotyl group">Crotyl</a></li>

<li><a href="Allenes" title="Allenes">Allene</a></li>

<li><a href="Cumulene" title="Cumulene">Cumulene</a></li></ul></li>

<ul><li><a href="Phenyl_group" title="Phenyl group">Phenyl</a></li>

<li><a href="Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li>

<li><a href="Alkyne" title="Alkyne">Alkyne</a></li>

<li><a href="Carbene" title="Carbene">Carbene</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="Carbon" title="Carbon">carbon</a>, <br><a href="Hydrogen" title="Hydrogen">hydrogen</a>, <br>and <a href="Oxygen" title="Oxygen">oxygen</a> <br><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Acetal" title="Acetal">Acetal</a></li>

<li><a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li>

<li><a href="Alkoxy_group" title="Alkoxy group">Alkoxy</a>

<ul><li><a href="Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li>

<li><a href="Ether" title="Ether">Ether</a>

<ul><li><a href="Enol_ether" title="Enol ether">Enol ether</a></li>

<li><a href="Epoxide" title="Epoxide">Epoxide</a></li></ul></li>

<li><a href="Organic_peroxides" title="Organic peroxides">Peroxy</a>

<ul><li><a href="Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li>

<li><a href="Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li>

<li><a href="Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li>

<li><a href="Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Acetyl_group" title="Acetyl group">Acetyl</a></li>

<li><a href="Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li>

<li><a href="Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li>

<li><a href="Aldehyde" title="Aldehyde">Aldehyde</a>

<ul><li><a href="Ketene" title="Ketene">Ketene</a></li></ul></li>

<li><a href="Ketone" title="Ketone">Ketone</a></li>

<li><a href="Ynone" title="Ynone">Ynone</a></li>

<li><a href="Reductone" title="Reductone">Reductone</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Carboxylic_acid" title="Carboxylic acid">Carboxyl</a>

<ul><li><a href="Acetoxy_group" title="Acetoxy group">Acetoxy</a></li>

<li><a href="Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li>

<li><a href="Ester" title="Ester">Ester</a>

<ul><li><a href="Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br>element, <br>not being <br>carbon, <br>hydrogen, <br>or oxygen <br><span class="nobold">(one element, <br>not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Amine" title="Amine">Amine</a>

<ul><li><a href="Enamine" title="Enamine">Enamine</a></li>

<li><a href="Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li>

<li><a href="Hydrazines" title="Hydrazines">Hydrazo</a></li>

<li><a href="Nitrene" title="Nitrene">Nitrene</a></li>

<li><a href="Imine" title="Imine">Imine</a></li>

<li><a href="Oxime" title="Oxime">Oxime</a></li>

<li><a href="Hydrazone" title="Hydrazone">Hydrazone</a></li>

<li><a href="Amide_(functional_group)" title="Amide (functional group)">Amide</a></li>

<li><a href="Imidate" class="mw-redirect" title="Imidate">Imidate</a></li>

<li><a href="Amidine" title="Amidine">Amidine</a></li>

<li><a href="Carbamate" title="Carbamate">Carbamate</a></li>

<li><a href="Imide" title="Imide">Imide</a></li>

<li><a href="Nitrile" title="Nitrile">Nitrile</a></li>

<li><a href="Isocyanide" title="Isocyanide">Isonitrile</a></li>

<li><a href="Cyanate_ester" title="Cyanate ester">Cyanate</a></li>

<li><a href="Isocyanate" title="Isocyanate">Isocyanate</a></li>

<li><a href="Nitrate_ester" title="Nitrate ester">Nitrate</a></li>

<li><a href="Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li>

<li><a href="Nitro_compound" title="Nitro compound">Nitro</a></li>

<li><a href="Nitroso" title="Nitroso">Nitroso</a></li>

<li><a href="NONOate" title="NONOate">NONOate</a></li>

<li><a href="Triazole" title="Triazole">Triazole</a></li>

<li><a href="Tetrazole" title="Tetrazole">Tetrazole</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Silane" title="Silane">Silane</a>

<ul><li><a href="Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li>

<li><a href="Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li>

<li><a href="Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li>

<li><a href="Silanol" title="Silanol">Silanol</a></li>

<li><a href="Siloxide" title="Siloxide">Siloxide</a></li>

<li><a href="Siloxane" title="Siloxane">Siloxane</a></li>

<li><a href="Silanone" title="Silanone">Silanone</a></li>

<li><a href="Silyl_ether" title="Silyl ether">Silether</a></li>

<li><a href="Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li>

<li><a href="Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li>

<li><a href="Silicate" title="Silicate">Silicate</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Organophosphate" title="Organophosphate">Phosphate</a>

<ul><li><a href="Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li>

<li><a href="Phosphonate" title="Phosphonate">Phosphonate</a>

<ul><li><a href="Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li>

<li><a href="Phosphonite" title="Phosphonite">Phosphonous</a></li>

<li><a href="Phosphinate" title="Phosphinate">Phosphinate</a></li>

<li><a href="Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li>

<li><a href="Organophosphine" title="Organophosphine">Phosphine</a>

<ul><li><a href="Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li>

<li><a href="Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li>

<li><a href="Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li>

<li><a href="1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Thiol" title="Thiol">Thiol</a></li>

<li><a href="Thioether" class="mw-redirect" title="Thioether">Thioether</a>

<ul><li><a href="Sulfonium" title="Sulfonium">Sulfonium</a></li>

<li><a href="Thia-crown_ether" title="Thia-crown ether">Thia-crown ether</a></li></ul></li>

<li><a href="Persulfide" title="Persulfide">Persulfide</a></li>

<li><a href="Disulfide" title="Disulfide">Disulfide</a></li>

<li><a href="Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li>

<li><a href="Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li>

<li><a href="Sulfoxide" title="Sulfoxide">Sulfoxide</a></li>

<li><a href="Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li>

<li><a href="Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li>

<li><a href="Sulfone" title="Sulfone">Sulfone</a></li>

<li><a href="Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li>

<li><a href="Thioketone" title="Thioketone">Thioketone</a></li>

<li><a href="Thial" title="Thial">Thial</a></li>

<li><a href="Thioester" title="Thioester">Thioester</a></li>

<li><a href="Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li>

<li><a href="Thioxanthate" title="Thioxanthate">Thioxanthate</a></li>

<li><a href="Xanthate" title="Xanthate">Xanthate</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Boronic_acid" title="Boronic acid">Boronic acid</a></li>

<li><a href="Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Selenol" title="Selenol">Selenol</a></li>

<li><a href="Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li>

<li><a href="Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li>

<li><a href="Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li>

<li><a href="Selone" title="Selone">Selone</a></li>

<li><a href="Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Tellurol" title="Tellurol">Tellurol</a></li>

<li><a href="Telluroketone" title="Telluroketone">Telluroketone</a></li>

<li><a href="Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li>

<li><a href="Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Haloalkane" title="Haloalkane">Haloalkane</a>

<ul><li><a href="Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li>

<li><a href="Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li>

<li><a href="Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li>

<li><a href="Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li>

<li><a href="Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li>

<li><a href="Vinyl_halide" title="Vinyl halide">Vinyl halide</a>

<ul><li><a href="Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li>

<li><a href="Acyl_halide" title="Acyl halide">Acyl halide</a>

<ul><li><a href="Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li>

<li><a href="Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li>

<li><a href="Phosphoramides" title="Phosphoramides">Phosphoramides</a></li>

<li><a href="Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li>

<li><a href="Sulfonamide" title="Sulfonamide">Sulfonamide</a></li>

<li><a href="Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li>

<li><a href="Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul>

</div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>

<dd><i><a href="Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd>

<dd><i><a href="Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i>

<dl><dd><a href="IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd>

<dd><a href="IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl>

</div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Concepts_in_organic_chemistry33" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Concepts_in_organic_chemistry33" style="font-size:114%;margin:0 4em">Concepts in <a href="Organic_chemistry" title="Organic chemistry">organic chemistry</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Aromaticity" title="Aromaticity">Aromaticity</a></li>

<li><a href="Covalent_bond" title="Covalent bond">Covalent bonding</a></li>

<li><a href="IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">Nomenclature</a></li>

<li><a href="Organic_compound" title="Organic compound">Organic compounds</a></li>

<li><a href="Organic_reaction" title="Organic reaction">Organic reactions</a></li>

<li><a href="Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li>

<li><a href="List_of_important_publications_in_chemistry" class="mw-redirect" title="List of important publications in chemistry">Publications</a></li>

<li><a href="Spectroscopy" title="Spectroscopy">Spectroscopy</a></li>

<li><a href="Stereochemistry" title="Stereochemistry">Stereochemistry</a></li>

<li><a href="List_of_organic_compounds" class="mw-redirect" title="List of organic compounds">List of organic compounds</a></li></ul>

</div></td></tr></tbody></table></div>

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