Functional group

Last updated
Example functional groups of benzyl acetate:
.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}
Ester group
Acetyl group
Benzyloxy group Benzyl acetate - functional groups and moieties.svg
Example functional groups of benzyl acetate:
   Ester group
   Acetyl group
   Benzyloxy group

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. [1] [2] This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

Contents

A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Functional groups can also be charged, e.g. in carboxylate salts (−COO), which turns the molecule into a polyatomic ion or a complex ion. Functional groups binding to a central atom in a coordination complex are called ligands . Complexation and solvation 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 solubility. For example, sugar dissolves in water because both share the hydroxyl functional group (−OH) and hydroxyls interact strongly with each other. Plus, when functional groups are more electronegative 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 aqueous environment.

Combining the names of functional groups with the names of the parent alkanes generates what is termed a systematic nomenclature for naming organic compounds. In traditional nomenclature, the first carbon atom after the carbon that attaches to the functional group is called the alpha carbon; 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 gamma-aminobutyric acid is on the third carbon of the carbon chain attached to the carboxylic acid group. IUPAC conventions call for numeric labeling of the position, e.g. 4-aminobutanoic acid. In traditional names various qualifiers are used to label isomers, for example, isopropanol (IUPAC name: propan-2-ol) is an isomer of n-propanol (propan-1-ol). The term moiety 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 aromatic ring, regardless of how many functional groups the said aryl has.

Table of common functional groups

The following is a list of common functional groups. [3] In the formulas, the symbols R and R' usually denote an attached hydrogen, or a hydrocarbon side chain of any length, but may sometimes refer to any group of atoms.

Hydrocarbons

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.

Chemical class GroupFormulaStructural FormulaPrefixSuffixExample
Alkane Alkyl R(CH2)nH Alkyl-(general)-skeletal.svg alkyl--ane Ethan Keilstrich.svg
Ethane
Alkene Alkenyl R2C=CR2 Alkene-2D-skeletal.svg alkenyl--ene Ethylene.svg
Ethylene
(Ethene)
Alkyne Alkynyl RC≡CR'alkynyl--yne
Acetylene
(Ethyne)
Benzene derivative Phenyl RC6H5
RPh
Phenyl-group.svg phenyl--benzene Cumene-skeletal.svg
Cumene
(Isopropylbenzene)

There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc. Hydrocarbons may form charged structures: positively charged carbocations or negative carbanions. Carbocations are often named -um. Examples are tropylium and triphenylmethyl cations and the cyclopentadienyl anion.

Groups containing halogen

Haloalkanes are a class of molecule that is defined by a carbon–halogen 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 fluorinated compounds, haloalkanes readily undergo nucleophilic substitution reactions or elimination reactions. The substitution on the carbon, the acidity of an adjacent proton, the solvent conditions, etc. all can influence the outcome of the reactivity.

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
haloalkane halo RXhalo-alkyl halide Chloroethane-skeletal.svg
Chloroethane
(Ethyl chloride)
fluoroalkane fluoro RFfluoro-alkyl fluoride Fluoromethane.svg
Fluoromethane
(Methyl fluoride)
chloroalkane chloro RClchloro-alkyl chloride Chloromethane.svg
Chloromethane
(Methyl chloride)
bromoalkane bromo RBrbromo-alkyl bromide Methyl bromide.svg
Bromomethane
(Methyl bromide)
iodoalkane iodo RIiodo-alkyl iodide Iodomethane.svg
Iodomethane
(Methyl iodide)

Groups containing oxygen

Compounds that contain C-O bonds each possess differing reactivity based upon the location and hybridization 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).

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
Alcohol Hydroxyl ROH
Hydroxyl Hydroxy-group-bw.svg
Hydroxyl
hydroxy--ol Methanol-2D.svg
Methanol
Ketone Ketone RCOR' Ketone-group-2D-skeletal.svg -oyl- (-COR')
or
oxo- (=O)
-one Butanone-skeletal-structure.svg
Butanone
(Methyl ethyl ketone)
Aldehyde Aldehyde RCHO Skeletal formula of an aldehyde group.svg formyl- (-COH)
or
oxo- (=O)
-al Acetaldehyde-skeletal.svg
Acetaldehyde
(Ethanal)
Acyl halide HaloformylRCOX Acyl-halide-skeletal2D.svg carbonofluoridoyl-
carbonochloridoyl-
carbonobromidoyl-
carbonoiodidoyl-
-oyl fluoride
-oyl chloride
-oyl bromide
-oyl iodide
Acetyl-chloride.svg
Acetyl chloride
(Ethanoyl chloride)
Carbonate Carbonate ester ROCOOR' Carbonate-group-skeletal.svg (alkoxycarbonyl)oxy-alkyl carbonate Triphosgen Strukturformel.svg
Triphosgene
(bis(trichloromethyl) carbonate)
Carboxylate Carboxylate RCOO
Carboxylate Carboxylate-resonance-hybrid.svg
Carboxylate

Carboxylate-canonical-forms.svg
carboxylato--oate Sodium-acetate-2D-skeletal.png
Sodium acetate
(Sodium ethanoate)
Carboxylic acid Carboxyl RCOOH Carboxylic-acid-skeletal.svg carboxy--oic acid Acetic-acid-2D-skeletal.svg
Acetic acid
(Ethanoic acid)
Ester Carboalkoxy RCOOR' Ester-skeletal.svg alkanoyloxy-
or
alkoxycarbonyl
alkyl alkanoate Ethyl butyrate.png
Ethyl butyrate
(Ethyl butanoate)
Hydroperoxide Hydroperoxy ROOH Hydroperoxide-group-2D.svg hydroperoxy-alkyl hydroperoxide TBHP.png
tert-Butyl hydroperoxide
Peroxide Peroxy ROOR' Peroxy-group.svg peroxy-alkyl peroxide Di-tert-butyl peroxide.svg
Di-tert-butyl peroxide
Ether Ether ROR'
Ether Ether-(general).svg
Ether
alkoxy-alkyl ether Diethyl ether chemical structure.svg
Diethyl ether
(Ethoxyethane)
Hemiacetal Hemiacetal R2CH(OR1)(OH) Hemiacetal general.svg alkoxy -ol-al alkyl hemiacetal
Hemiketal Hemiketal RC(ORʺ)(OH)R' Hemiketal-2D-skeletal.png alkoxy -ol-one alkyl hemiketal
Acetal Acetal RCH(OR')(OR") Acetal-2D-skeletal.png dialkoxy--al dialkyl acetal
Ketal (or Acetal) Ketal (or Acetal)RC(OR")(OR‴)R' Ketal-2D-skeletal.png dialkoxy--one dialkyl ketal
Orthoester Orthoester RC(OR')(OR")(OR‴) Orthoester general structure.svg trialkoxy-
Heterocycle
(if cyclic)
Methylenedioxy (–OCH2O–)

Methylenedioxy graphic (ChemDraw).png

methylenedioxy--dioxole Benzo(d)(1,3)dioxole 200.svg
1,2-Methylenedioxybenzene
(1,3-Benzodioxole)
Orthocarbonate ester Orthocarbonate ester C(OR)(OR')(OR")(OR‴) Orthocarbonate-ester.svg tetralkoxy-tetraalkylorthocarbonate Tetramethylorthocarbonat.svg
Tetramethoxymethane
Organic acid anhydride Carboxylic anhydride R1(CO)O(CO)R2 FunktionelleGruppen Carbonsaureanhydrid.svg anhydride Butyric anhydride.svg
Butyric anhydride

Groups containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
Amide Carboxamide RCONR'R" Amide-(tertiary)-skeletal.svg carboxamido-
or
carbamoyl-
-amide Acetamide skeletal.svg
Acetamide
(Ethanamide)
Amidine Amidine RC(NR)NR2 Amidines.svg amidino--amidine Acetamidine-2D-skeletal.png acetamidine

(acetimidamide)

Amines Primary amine RNH2 1deg-amino-group.png amino--amine Methylamine-2D.png
Methylamine
(Methanamine)
Secondary amine R'R"NH Amine-(secondary).png amino--amine Dimethylamine-2D.png
Dimethylamine
Tertiary amine R3N Amine-(tertiary).png amino--amine Trimethylamine chemical structure.png
Trimethylamine
4° ammonium ion R4N+ Quaternary-ammonium-cation.svg ammonio--ammonium Choline-skeletal.svg
Choline
Hydrazone R'R"CN2H2
Hydrazone-2D.png
hydrazino--hydrazine
Benzophenone Benzophenone hydrazone-structure.png
Benzophenone
Imine Primary ketimine RC(=NH)R' Imine-(primary)-skeletal.svg imino--imine
Secondary ketimine Imine-(secondary)-skeletal.svg imino--imine
Primary aldimine RC(=NH)H Aldimine-(primary)-skeletal.svg imino--imine Ethanimine skeletal.svg
Ethanimine
Secondary aldimine RC(=NR')H Aldimine-(secondary)-skeletal.svg imino--imine
Imide Imide (RCO)2NR' Imide-group.svg imido--imide Succinimide.svg
Succinimide
(Pyrrolidine-2,5-dione)
Azide Azide RN3 Azide-2D.svg azido-alkyl azide Phenyl azide-chemical.png
Phenyl azide
(Azidobenzene)
Azo compound Azo
(Diimide)
RN2R' Azo-group.svg azo--diazene Methyl-orange-skeletal.png
Methyl orange
(p-dimethylamino-azobenzenesulfonic acid)
Cyanates Cyanate ROCN Cyanate-group.svg cyanato-alkyl cyanate Methyl cyanate.svg
Methyl cyanate
Isocyanate RNCO Isocyanate-group.svg isocyanato-alkyl isocyanate Methyl-isocyanate.svg
Methyl isocyanate
Nitrate Nitrate RONO2 Nitrate-group-2D.svg nitrooxy-, nitroxy-

alkyl nitrate

Amyl nitrate.svg
Amyl nitrate
(1-nitrooxypentane)
Nitrile Nitrile RCNcyano-alkanenitrile
alkyl cyanide
Benzonitrile structure.png
Benzonitrile
(Phenyl cyanide)
Isonitrile RNC
Isonitrile structural formula.svg
isocyano-alkaneisonitrile
alkyl isocyanide

Methyl isocyanide
Nitrite Nitrosooxy RONO Nitrite-group-2D.svg nitrosooxy-

alkyl nitrite

Amyl nitrite.svg
Isoamyl nitrite
(3-methyl-1-nitrosooxybutane)
Nitro compound Nitro RNO2 Nitro-group.svg nitro-  Nitromethane2.png
Nitromethane
Nitroso compound Nitroso RNO Nitroso-compound-2D.svg nitroso- (Nitrosyl-)  Nitrosobenzene.png
Nitrosobenzene
Oxime Oxime RCH=NOH General structure of oximes.svg   Oxime Acetoxime.svg
Acetone oxime
(2-Propanone oxime)
Pyridine derivative Pyridyl RC5H4N

4-pyridyl.svg
3-pyridyl.svg
2-pyridyl.svg

4-pyridyl
(pyridin-4-yl)

3-pyridyl
(pyridin-3-yl)

2-pyridyl
(pyridin-2-yl)

-pyridine Nicotine-2D-skeletal.png
Nicotine
Carbamate ester Carbamate RO(C=O)NR2 Carbamate-group-2D-skeletal.png (-carbamoyl)oxy--carbamate Isopropyl (3-chlorophenyl)carbamate 200.svg
Chlorpropham
(Isopropyl (3-chlorophenyl)carbamate)

Groups containing sulfur

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.

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
Thiol Sulfhydryl RSH Thiol-group.svg sulfanyl-
(-SH)
-thiol Ethanethiol-skeletal.svg
Ethanethiol
Sulfide
(Thioether)
Sulfide RSR' Sulfide-group-2D.svg substituent sulfanyl-
(-SR')
di(substituent) sulfide
Dimethylsulfide.png

(Methylsulfanyl)methane  (prefix) or
Dimethyl sulfide (suffix)
Disulfide Disulfide RSSR' Disulfide general formula.svg substituent disulfanyl-
(-SSR')
di(substituent) disulfide
Dimethyl disulfide.PNG

(Methyldisulfanyl)methane  (prefix) or
Dimethyl disulfide (suffix)
Sulfoxide Sulfinyl RSOR' Sulfoxide-2D.svg -sulfinyl-
(-SOR')
di(substituent) sulfoxide Dimethylsulfoxid.svg
(Methanesulfinyl)methane  (prefix) or
Dimethyl sulfoxide (suffix)
Sulfone Sulfonyl RSO2R' Sulfone-2D.svg -sulfonyl-
(-SO2R')
di(substituent) sulfone DMSO2.svg
(Methanesulfonyl)methane  (prefix) or
Dimethyl sulfone (suffix)
Sulfinic acid SulfinoRSO2H Sulfinic-acid-2D.svg sulfino-
(-SO2H)
-sulfinic acid Hypotaurine.png
2-Aminoethanesulfinic acid
Sulfonic acid SulfoRSO3H Sulfonic-acid.svg sulfo-
(-SO3H)
-sulfonic acid Benzenesulfonic-acid-2D-skeletal.png
Benzenesulfonic acid
Sulfonate ester SulfoRSO3R' Sulfonic-ester.svg (-sulfonyl)oxy-
or
alkoxysulfonyl-
R'R-sulfonate StructureMeOTf.svg
Methyl trifluoromethanesulfonate or
Methoxysulfonyl trifluoromethane (prefix)
Thiocyanate Thiocyanate RSCN Thiocyanate-group.svg thiocyanato-
(-SCN)
substituent thiocyanate Phenyl thiocyanate.svg
Phenyl thiocyanate
Isothiocyanate RNCS Isothiocyanate-group.svg isothiocyanato-
(-NCS)
substituent isothiocyanate Allyl-isothiocyanate-2D-skeletal.png
Allyl isothiocyanate
Thioketone Carbonothioyl RCSR' Thioketone-skeletal.svg -thioyl-
(-CSR')
or
sulfanylidene-
(=S)
-thione Thiobenzophenone-2D-skeletal.png
Diphenylmethanethione
(Thiobenzophenone)
Thial Carbonothioyl RCSH Thial-skeletal.svg methanethioyl-
(-CSH)
or
sulfanylidene-
(=S)
-thial
Thiocarboxylic acid Carbothioic S-acidRC=OSH
Thioic S-acid Thioic acid.svg
Thioic S-acid
mercaptocarbonyl--thioicS-acid Thiobenzoic acid.svg
Thiobenzoic acid
(benzothioic S-acid)
Carbothioic O-acidRC=SOH
Thioic O-acid Thioic O-acid.svg
Thioic O-acid
hydroxy(thiocarbonyl)--thioicO-acid
Thioester ThiolesterRC=OSR' Thiolester-skeletal.svg S-alkyl-alkane-thioate S-methyl-thioacrylate-2D-skeletal.png
S-methyl thioacrylate
(S-methyl prop-2-enethioate)
ThionoesterRC=SOR' Thionoester-skeletal.svg O-alkyl-alkane-thioate
Dithiocarboxylic acid Carbodithioic acidRCS2H
Dithiocarboxylic acid Dithioic-acid-skeletal.svg
Dithiocarboxylic acid
dithiocarboxy--dithioic acid PhCS2H.svg
Dithiobenzoic acid
(Benzenecarbodithioic acid)
Dithiocarboxylic acid ester CarbodithioRC=SSR' Dithioic-acid-ester-skeletal.svg -dithioate

Groups containing phosphorus

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.

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
Phosphine
(Phosphane)
PhosphinoR3P Phosphine-general.svg phosphanyl--phosphane Methylpropylphosphane-skeletal.svg
Methylpropylphosphane
Phosphonic acid Phosphono Phosphonic-acid.svg phosphono-substituentphosphonic acid Benzylphosphonic-acid-2D-skeletal.png
Benzylphosphonic acid
Phosphate Phosphate Phosphate-group.svg phosphonooxy-
or
O-phosphono- (phospho-)
substituentphosphate G3P-2D-skeletal.png
Glyceraldehyde 3-phosphate (suffix)
Phosphocholine.png
O-Phosphonocholine (prefix)
(Phosphocholine)
Phosphodiester Phosphate HOPO(OR)2 Phosphodiester-group.svg [(alkoxy)hydroxyphosphoryl]oxy-
or
O-[(alkoxy)hydroxyphosphoryl]-
di(substituent) hydrogen phosphate
or
phosphoric acid di(substituent) ester
DNA
O‑[(2‑Guanidinoethoxy)hydroxyphosphoryl]‑l‑serine (prefix)
(Lombricine)

Groups containing boron

Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as Lewis acids.

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
Boronic acid BoronoRB(OH)2
Boronic-acid-2D.svg
Borono-substituent
boronic acid
Boronic ester BoronateRB(OR)2
Boronate-ester-2D.svg
O-[bis(alkoxy)alkylboronyl]-substituent
boronic acid
di(substituent) ester
Borinic acid BorinoR2BOH
Borinic-acid-2D.svg
Hydroxyborino-di(substituent)
borinic acid
Borinic ester BorinateR2BOR
Borinate-ester-2D.svg
O-[alkoxydialkylboronyl]-di(substituent)
borinic acid
substituentester
2-APB.png
Diphenylborinic acid 2-aminoethyl ester
(2-Aminoethoxydiphenyl borate)

Groups containing metals

Chemical classStructural formulaPrefixSuffixExample
Alkyllithium RLi(tri/di)alkyl--lithium Meli is.svg

methyllithium

Alkylmagnesium halide RMgX (X=Cl, Br, I) [note 1] -magnesium halide Methylmagnesiumchloride.svg

methylmagnesium chloride

Alkylaluminium Al2R6-aluminium Trimethylaluminium-from-xtal-3D-bs-17.png

trimethylaluminium

Silyl ether R3SiOR-silyl ether Trimethylsilyl triflate.svg

trimethylsilyl triflate

note 1 Fluorine is too electronegative to be bonded to magnesium; it becomes an ionic salt instead.

Names of radicals or moieties

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.

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. "ethyne" becomes "ethynyl"). [4]

When used to refer to moieties, multiple single bonds differ from a single multiple bond. For example, a methylene bridge (methanediyl) has two single bonds, whereas a methylene group (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).

There are some retained names, such as methylene for methanediyl, 1,x-phenylene for phenyl-1,x-diyl (where x is 2, 3, or 4), [5] carbyne for methylidyne, and trityl for triphenylmethyl.

Chemical class GroupFormulaStructural formulaPrefixSuffixExample
Single bondR•Ylo- [6] -yl
Double bondR: ?-ylidene
Triple bondR⫶ ?-ylidyne
Carboxylic acyl radicalAcylR−C(=O)• ?-oyl

See also

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Alkene</span> Hydrocarbon compound containing one or more C=C bonds

In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.

<span class="mw-page-title-main">Alkyne</span> Hydrocarbon compound containing one or more C≡C bonds

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two organyl groups. They have the general formula R−O−R′, where R and R′ represent organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

<span class="mw-page-title-main">Organic chemistry</span> Subdiscipline of chemistry, focusing on carbon compounds

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical study.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

<span class="mw-page-title-main">Acyl group</span> Chemical group (R–C=O)

In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group or hydrogen in the case of formyl group. In organic chemistry, the acyl group is usually derived from a carboxylic acid, in which case it has the formula R−C(=O)−, where R represents an organyl group or hydrogen. Although the term is almost always applied to organic compounds, acyl groups can in principle be derived from other types of acids such as sulfonic acids and phosphonic acids. In the most common arrangement, acyl groups are attached to a larger molecular fragment, in which case the carbon and oxygen atoms are linked by a double bond.

<span class="mw-page-title-main">Cycloalkane</span> Saturated alicyclic hydrocarbon

In organic chemistry, the cycloalkanes are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring, and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkenes.

<span class="mw-page-title-main">Ethyl group</span> Chemical group (–CH₂–CH₃)

In organic chemistry, an ethyl group is an alkyl substituent with the formula −CH2CH3, derived from ethane. Ethyl is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated two-carbon moiety in a molecule, while the prefix "eth-" is used to indicate the presence of two carbon atoms in the molecule.

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula −CH3.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

In organic chemistry, a substituent is one or a group of atoms that replaces atoms, thereby becoming a moiety in the resultant (new) molecule.

In organic chemistry, a methine group or methine bridge is a trivalent functional group =CH−, derived formally from methane. It consists of a carbon atom bound by two single bonds and one double bond, where one of the single bonds is to a hydrogen. The group is also called methyne or methene, but its IUPAC systematic name is methylylidene or methanylylidene.

In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is R−:C−R' or R=C: where the R represents substituents or hydrogen atoms.

<span class="mw-page-title-main">Cyclic compound</span> Molecule with a ring of bonded atoms

A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.

<span class="mw-page-title-main">Methylidyne radical</span> Chemical compound

Methylidyne, or (unsubstituted) carbyne, is an organic compound whose molecule consists of a single hydrogen atom bonded to a carbon atom. It is the parent compound of the carbynes, which can be seen as obtained from it by substitution of other functional groups for the hydrogen.

This glossary of chemistry terms is a list of terms and definitions relevant to chemistry, including chemical laws, diagrams and formulae, laboratory tools, glassware, and equipment. Chemistry is a physical science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions; it features an extensive vocabulary and a significant amount of jargon.

Methylene is an organic compound with the chemical formula CH
2
. It is a colourless gas that fluoresces in the mid-infrared range, and only persists in dilution, or as an adduct.

References

  1. Compendium of Chemical Terminology (IUPAC "Gold Book") functional group
  2. March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN   9780471854722, OCLC   642506595
  3. Brown, Theodore (2002). Chemistry: the central science. Upper Saddle River, NJ: Prentice Hall. p. 1001. ISBN   0130669970.
  4. 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.
  5. "R-2. 5 Substituent Prefix Names Derived from Parent Hydrides". IUPAC. 1993. section P-56.2.1
  6. "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.