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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.
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.
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 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 | Group | Formula | Structural Formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Alkane | Alkyl | R(CH2)nH | alkyl- | -ane | Ethane | |
Alkene | Alkenyl | R2C=CR2 | alkenyl- | -ene | Ethylene (Ethene) | |
Alkyne | Alkynyl | RC≡CR' | alkynyl- | -yne | Acetylene (Ethyne) | |
Benzene derivative | Phenyl | RC6H5 RPh | phenyl- | -benzene | Cumene (Isopropylbenzene) | |
There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc. There are several functional groups that contain an alkene such as vinyl group, allyl group, or acrylic group. 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.
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 | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
haloalkane | halo | RX | halo- | alkyl halide | Chloroethane (Ethyl chloride) | |
fluoroalkane | fluoro | RF | fluoro- | alkyl fluoride | Fluoromethane (Methyl fluoride) | |
chloroalkane | chloro | RCl | chloro- | alkyl chloride | Chloromethane (Methyl chloride) | |
bromoalkane | bromo | RBr | bromo- | alkyl bromide | Bromomethane (Methyl bromide) | |
iodoalkane | iodo | RI | iodo- | alkyl iodide | Iodomethane (Methyl iodide) | |
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 | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Alcohol | Hydroxyl | ROH | hydroxy- | -ol | Methanol | |
Ketone | Ketone | RCOR' | -oyl- (-COR') or oxo- (=O) | -one | Butanone (Methyl ethyl ketone) | |
Aldehyde | Aldehyde | RCHO | formyl- (-COH) or oxo- (=O) | -al | Acetaldehyde (Ethanal) | |
Acyl halide | Haloformyl | RCOX | carbonofluoridoyl- carbonochloridoyl- carbonobromidoyl- carbonoiodidoyl- | -oyl fluoride -oyl chloride -oyl bromide -oyl iodide | Acetyl chloride (Ethanoyl chloride) | |
Carbonate | Carbonate ester | ROCOOR' | (alkoxycarbonyl)oxy- | alkyl carbonate | Triphosgene (bis(trichloromethyl) carbonate) | |
Carboxylate | Carboxylate | RCOO− | carboxylato- | -oate | Sodium acetate (Sodium ethanoate) | |
Carboxylic acid | Carboxyl | RCOOH | carboxy- | -oic acid | Acetic acid (Ethanoic acid) | |
Ester | Carboalkoxy | RCOOR' | alkanoyloxy- or alkoxycarbonyl | alkyl alkanoate | Ethyl butyrate (Ethyl butanoate) | |
Hydroperoxide | Hydroperoxy | ROOH | hydroperoxy- | alkyl hydroperoxide | tert-Butyl hydroperoxide | |
Peroxide | Peroxy | ROOR' | peroxy- | alkyl peroxide | Di-tert-butyl peroxide | |
Ether | Ether | ROR' | alkoxy- | alkyl ether | Diethyl ether (Ethoxyethane) | |
Hemiacetal | Hemiacetal | R2CH(OR1)(OH) | alkoxy -ol | -al alkyl hemiacetal | ||
Hemiketal | Hemiketal | RC(ORʺ)(OH)R' | alkoxy -ol | -one alkyl hemiketal | ||
Acetal | Acetal | RCH(OR')(OR") | dialkoxy- | -al dialkyl acetal | ||
Ketal (or Acetal) | Ketal (or Acetal) | RC(OR")(OR‴)R' | dialkoxy- | -one dialkyl ketal | ||
Orthoester | Orthoester | RC(OR')(OR")(OR‴) | trialkoxy- | |||
Heterocycle (if cyclic) | Methylenedioxy | (–OCH2O–) | methylenedioxy- | -dioxole | 1,2-Methylenedioxybenzene (1,3-Benzodioxole) | |
Orthocarbonate ester | Orthocarbonate ester | C(OR)(OR')(OR")(OR‴) | tetralkoxy- | tetraalkylorthocarbonate | Tetramethoxymethane | |
Organic acid anhydride | Carboxylic anhydride | R1(CO)O(CO)R2 | anhydride | Butyric anhydride |
Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.
Chemical class | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Amide | Carboxamide | RCONR'R" | carboxamido- or carbamoyl- | -amide | Acetamide (Ethanamide) | |
Amidine | Amidine | R4C(NR1)(NR2R3) | amidino- | -amidine | acetamidine (acetimidamide) | |
Guanidine | Guanidine | RNC(NR2)2) | Guanidin- | -Guanidine | Guanidinopropionic acid | |
Amines | Primary amine | RNH2 | amino- | -amine | Methylamine (Methanamine) | |
Secondary amine | R'R"NH | amino- | -amine | Dimethylamine | ||
Tertiary amine | R3N | amino- | -amine | Trimethylamine | ||
4° ammonium ion | R4N+ | ammonio- | -ammonium | Choline | ||
Hydrazone | R'R"CN2H2 | hydrazino- | -hydrazine | |||
Imine | Primary ketimine | RC(=NH)R' | imino- | -imine | ||
Secondary ketimine | imino- | -imine | ||||
Primary aldimine | RC(=NH)H | imino- | -imine | Ethanimine | ||
Secondary aldimine | RC(=NR')H | imino- | -imine | |||
Imide | Imide | (RCO)2NR' | imido- | -imide | Succinimide (Pyrrolidine-2,5-dione) | |
Azide | Azide | RN3 | azido- | alkyl azide | Phenyl azide (Azidobenzene) | |
Azo compound | Azo (Diimide) | RN2R' | azo- | -diazene | Methyl orange (p-dimethylamino-azobenzenesulfonic acid) | |
Cyanates | Cyanate | ROCN | cyanato- | alkyl cyanate | Methyl cyanate | |
Isocyanate | RNCO | isocyanato- | alkyl isocyanate | Methyl isocyanate | ||
Nitrate | Nitrate | RONO2 | nitrooxy-, nitroxy- | alkyl nitrate | Amyl nitrate (1-nitrooxypentane) | |
Nitrile | Nitrile | RCN | cyano- | alkanenitrile alkyl cyanide | Benzonitrile (Phenyl cyanide) | |
Isonitrile | RNC | isocyano- | alkaneisonitrile alkyl isocyanide | Methyl isocyanide | ||
Nitrite | Nitrosooxy | RONO | nitrosooxy- | alkyl nitrite | Isoamyl nitrite (3-methyl-1-nitrosooxybutane) | |
Nitro compound | Nitro | RNO2 | nitro- | Nitromethane | ||
Nitroso compound | Nitroso | RNO | nitroso- (Nitrosyl-) | Nitrosobenzene | ||
Oxime | Oxime | RCH=NOH | Oxime | Acetone oxime (2-Propanone oxime) | ||
Pyridine derivative | Pyridyl | RC5H4N | 4-pyridyl 3-pyridyl 2-pyridyl | -pyridine | Nicotine | |
Carbamate ester | Carbamate | RO(C=O)NR2 | (-carbamoyl)oxy- | -carbamate | Chlorpropham (Isopropyl (3-chlorophenyl)carbamate) | |
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 | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Thiol | Sulfhydryl | RSH | sulfanyl- (-SH) | -thiol | Ethanethiol | |
Sulfide (Thioether) | Sulfide | RSR' | substituent sulfanyl- (-SR') | di(substituent) sulfide | (Methylsulfanyl)methane (prefix) or Dimethyl sulfide (suffix) | |
Disulfide | Disulfide | RSSR' | substituent disulfanyl- (-SSR') | di(substituent) disulfide | (Methyldisulfanyl)methane (prefix) or Dimethyl disulfide (suffix) | |
Sulfoxide | Sulfinyl | RSOR' | -sulfinyl- (-SOR') | di(substituent) sulfoxide | (Methanesulfinyl)methane (prefix) or Dimethyl sulfoxide (suffix) | |
Sulfone | Sulfonyl | RSO2R' | -sulfonyl- (-SO2R') | di(substituent) sulfone | (Methanesulfonyl)methane (prefix) or Dimethyl sulfone (suffix) | |
Sulfinic acid | Sulfino | RSO2H | sulfino- (-SO2H) | -sulfinic acid | 2-Aminoethanesulfinic acid | |
Sulfonic acid | Sulfo | RSO3H | sulfo- (-SO3H) | -sulfonic acid | Benzenesulfonic acid | |
Sulfonate ester | Sulfo | RSO3R' | (-sulfonyl)oxy- or alkoxysulfonyl- | R'R-sulfonate | Methyl trifluoromethanesulfonate or Methoxysulfonyl trifluoromethane (prefix) | |
Thiocyanate | Thiocyanate | RSCN | thiocyanato- (-SCN) | substituent thiocyanate | Phenyl thiocyanate | |
Isothiocyanate | RNCS | isothiocyanato- (-NCS) | substituent isothiocyanate | Allyl isothiocyanate | ||
Thioketone | Carbonothioyl | RCSR' | -thioyl- (-CSR') or sulfanylidene- (=S) | -thione | Diphenylmethanethione (Thiobenzophenone) | |
Thial | Carbonothioyl | RCSH | methanethioyl- (-CSH) or sulfanylidene- (=S) | -thial | ||
Thiocarboxylic acid | Carbothioic S-acid | RC=OSH | mercaptocarbonyl- | -thioicS-acid | Thiobenzoic acid (benzothioic S-acid) | |
Carbothioic O-acid | RC=SOH | hydroxy(thiocarbonyl)- | -thioicO-acid | |||
Thioester | Thiolester | RC=OSR' | S-alkyl-alkane-thioate | S-methyl thioacrylate (S-methyl prop-2-enethioate) | ||
Thionoester | RC=SOR' | O-alkyl-alkane-thioate | ||||
Dithiocarboxylic acid | Carbodithioic acid | RCS2H | dithiocarboxy- | -dithioic acid | Dithiobenzoic acid (Benzenecarbodithioic acid) | |
Dithiocarboxylic acid ester | Carbodithio | RC=SSR' | -dithioate |
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 | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Phosphine (Phosphane) | Phosphino | R3P | phosphanyl- | -phosphane | Methylpropylphosphane | |
Phosphonic acid | Phosphono | phosphono- | substituentphosphonic acid | Benzylphosphonic acid | ||
Phosphate | Phosphate | phosphonooxy- or O-phosphono- (phospho-) | substituentphosphate | Glyceraldehyde 3-phosphate (suffix) | ||
O-Phosphonocholine (prefix) (Phosphocholine) | ||||||
Phosphodiester | Phosphate | HOPO(OR)2 | [(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) |
Compounds containing boron exhibit unique chemistry due to their having partially filled octets and therefore acting as Lewis acids.
Chemical class | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Boronic acid | Borono | RB(OH)2 | Borono- | substituent boronic acid | ||
Boronic ester | Boronate | RB(OR)2 | O-[bis(alkoxy)alkylboronyl]- | substituent boronic acid di(substituent) ester | ||
Borinic acid | Borino | R2BOH | Hydroxyborino- | di(substituent) borinic acid | ||
Borinic ester | Borinate | R2BOR | O-[alkoxydialkylboronyl]- | di(substituent) borinic acid substituentester |
Chemical class | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|
Alkyllithium | RLi | (tri/di)alkyl- | -lithium | |
Alkylmagnesium halide | RMgX (X=Cl, Br, I) [note 1] | -magnesium halide | ||
Alkylaluminium | Al2R6 | -aluminium | ||
Silyl ether | R3SiOR | -silyl ether |
note 1 Fluorine is too electronegative to be bonded to magnesium; it becomes an ionic salt instead.
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 methylidene 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 | Group | Formula | Structural formula | Prefix | Suffix | Example |
---|---|---|---|---|---|---|
Single bond | R• | Ylo- [6] | -yl | |||
Double bond | R: | ? | -ylidene | |||
Triple bond | R⫶ | ? | -ylidyne | |||
Carboxylic acyl radical | Acyl | R−C(=O)• | ? | -oyl |
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.
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.
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.
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 an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom bonded to two organyl groups. They have the general formula R−O−R′, where R and R′ represent the 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.
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.
In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.
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.
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.
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.
The root alk- is used in organic chemistry to form classification names for classes of organic compounds which contain a carbon skeleton but no aromatic rings. It was extracted from the word alcohol by removing the -ol suffix. See e.g. alkyl, alkane.
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.
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.
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes.
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.
In organic chemistry, alkylidene is a general term for divalent functional groups of the form R2C=, where each R is an alkane or hydrogen. They can be considered the functional group corresponding to mono- or disubstituted divalent carbenes, or as the result of removing two hydrogen atoms from the same carbon atom in an alkane.