Information about Functional Group
In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction(s) regardless of the size of the molecule it is a part of.
Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming organic compounds.
The non-hydrogen atoms of functional groups are always associated with each other and with the rest of the molecule by covalent bonds. When the group of atoms is associated with the rest of the molecule primarily by ionic forces, the group is referred to more properly as a polyatomic ion or complex ion. And all of these are called radicals, by a meaning of the term radical that predates the free radical.
The first carbon atom after the carbon that attaches to the functional group is called the alpha carbon.
Functional groups are attached to the carbon backbone of organic molecules. They determine the characteristics and chemical reactivity of molecules. Functional groups are far less stable than the carbon backbone and are likely to participate in chemical reactions.
Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming organic compounds.
The non-hydrogen atoms of functional groups are always associated with each other and with the rest of the molecule by covalent bonds. When the group of atoms is associated with the rest of the molecule primarily by ionic forces, the group is referred to more properly as a polyatomic ion or complex ion. And all of these are called radicals, by a meaning of the term radical that predates the free radical.
The first carbon atom after the carbon that attaches to the functional group is called the alpha carbon.
Functional groups are attached to the carbon backbone of organic molecules. They determine the characteristics and chemical reactivity of molecules. Functional groups are far less stable than the carbon backbone and are likely to participate in chemical reactions.
Table of common functional groups
The following is a list of common functional groups. 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
Functional groups which vary based upon the number and order of π bonds impart different chemistry. Each listing below contains C-H bonds, but each one differs in type (and scope) of reactivity.| Chemical class | Group | Formula | Structural Formula | Prefix | Suffix | Example |
|---|---|---|---|---|---|---|
| Alkane | Alkyl | RH | -skeletal.png')){kind=small} | alkyl- | -ane | ) Methane |
| Alkene | Alkenyl | R2C=CR2 | -skeletal.png')) | alkenyl- | -ene | ) Ethylene (Ethene) |
| Alkyne | Alkynyl | RC≡CR' | -skeletal.png')){kind=small} | alkynyl- | -yne | ){kind=small} Acetylene (Ethyne) |
| Benzene derivative | Phenyl | RC6H5 | ){kind=small} | phenyl- | -benzene | ) Cumene (2-phenylpropane) |
| Toluene derivative | Benzyl | RCH2C6H5 RBn | ){kind=small} | benzyl- | 1-(substituent)toluene | Benzyl bromide (1-Bromotoluene) |
Groups containing halogens
Haloalkanes are a class of molecule which 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 | ){kind=small} | halo- | alkyl halide | ){kind=small} Chloroethane (Ethyl chloride) |
| fluoroalkane | fluoro | RF | ){kind=small} | fluoro- | alkyl fluoride | ) Fluoromethane (Methyl fluoride) |
| chloroalkane | chloro | RCl | ){kind=small} | chloro- | alkyl chloride | ) Chloromethane (Methyl chloride) |
| bromoalkane | bromo | RBr | ){kind=small} | bromo- | alkyl bromide | ) Bromomethane (Methyl bromide) |
| iodoalkane | iodo | RI | ){kind=small} | iodo- | alkyl iodide | ) Iodomethane (Methyl iodide) |
Groups containing oxygen
Compounds which 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 sp2 hybridized oxygen and the donating effects of sp3 hybridized oxygen.| Chemical class | Group | Formula | Structural Formula | Prefix | Suffix | Example |
|---|---|---|---|---|---|---|
| Acyl halide | Haloformyl | RCOX | ) | haloformyl- | -oyl halide | ) Acetyl chloride (Ethanoyl chloride) |
| Alcohol | Hydroxyl | ROH | -skeletal.png')) | hydroxy- | -ol | ) Methanol |
| Ketone | Carbonyl | RCOR' | ) | keto-, oxo- | -one | ) Methyl ethyl ketone (Butanone) |
| Aldehyde | Aldehyde | RCHO | ) | aldo- | -al | ){kind=spacer} Acetaldehyde (Ethanal) |
| Carbonate | Carbonate ester | ROCOOR | ){kind=small} | alkyl carbonate | ||
| Carboxylate | Carboxylate | RCOO− | ) ){kind=small} | carboxy- | -oate | ){kind=small} Sodium acetate (Sodium ethanoate) |
| Carboxylic acid | Carboxyl | RCOOH | ) | carboxy- | -oic acid | ) Acetic acid (Ethanoic acid) |
| Ether | Ether | ROR' | .png')){kind=small} | alkoxy- | alkyl alkyl ether | ){kind=small} Diethyl ether (Ethoxyethane) |
| Ester | Ester | RCOOR' | ) | alkyl alkanoate | ){kind=small} Ethyl butyrate (Ethyl butanoate) | |
| Hydroperoxide | Hydroperoxy | ROOH | ){kind=small} | hydroperoxy- | alkyl hydroperoxide | ){kind=small} Methyl ethyl ketone peroxide |
| Peroxide | Peroxy | ROOR | ) | peroxy- | alkyl peroxide | ){kind=small} Di-tert-butyl peroxide |
Groups containing nitrogen
Compounds which 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 | RCONR2 | -skeletal.png')) | carboxamido- | -amide | ) Acetamide (Ethanamide) |
| Amines | Primary amine | RNH2 | amino- | -amine | ) Methylamine (Methanamine) | |
| Secondary amine | R2NH | .png')) | amino- | -amine | ){kind=small} Dimethylamine | |
| Tertiary amine | R3N | .png')) | amino- | -amine | ) Trimethylamine | |
| 4° ammonium ion | R4N+ | ) | ammonio- | -ammonium | ) choline Choline | |
| Imine | Primary ketimine | RC(=NH)R' | -skeletal.png')) | imino- | -imine | |
| Secondary ketimine | RC(=NR'')R' | -skeletal.png')) | imino- | -imine | ||
| Primary aldimine | RC(=NH)H | -skeletal.png')) | imino- | -imine | ||
| Secondary aldimine | RC(=NR')H | -skeletal.png')) | imino- | -imine | ||
| Imide | Imide | RC(=O)NC(=O)R' | ) | imido- | -imide | |
| Azide | Azide | RN3 | ){kind=small} | azido- | alkyl azide | ) Phenyl azide (Azidobenzene) |
| Azo compound | Azo (Diimide) | RN2R' | ) | azo- | -diazene | ) Methyl orange Methyl orange (p-dimethylamino-azobenzenesulfonic acid) |
| Cyanates | Cyanate | ROCN | ){kind=small} | cyanato- | alkyl cyanate | |
| Isocyanide | RNC | ){kind=small} | isocyano- | alkyl isocyanide | ||
| Isocyanates | Isocyanate | RNCO | ){kind=small} | isocyanato- | alkyl isocyanate | ){kind=small} Methyl isocyanate |
| Isothiocyanate | RNCS | ){kind=small} | isothiocyanato- | alkyl isothiocyanate | Allyl isothiocyanate | |
| Nitrate | Nitrate | RONO2 | ){kind=small} | nitrooxy-, nitroxy- | alkyl nitrate | ) Amyl nitrate Amyl nitrate (1-nitrooxypentane) |
| Nitrile | Nitrile | RCN | -skeletal.png')){kind=small} | cyano- |
alkanenitrile alkyl cyanide | ) Benzonitrile (Phenyl cyanide) |
| Nitrite | Nitrosooxy | RONO | ){kind=small} | nitrosooxy- | alkyl nitrite | Amyl nitrite (3-methyl-1-nitrosooxybutane) |
| Nitro compound | Nitro | RNO2 | ) | nitro- | ) Nitromethane | |
| Nitroso compound | Nitroso | RNO | ){kind=small} | nitroso- | ){kind=small} Nitrosobenzene | |
| Pyridine derivative | Pyridyl | RC5H4N |
){kind=small} ){kind=small} ) |
4-pyridyl (pyridin-4-yl) 3-pyridyl (pyridin-3-yl) 2-pyridyl (pyridin-2-yl) | -pyridine | ) Nicotine |
Groups containing phosphorus and sulfur
Compounds which contain sulfur and phosphorus exhibit unique chemistry due to their ability to form more bonds than nitrogen and oxygen, their lighter analogues on the periodic table.| Chemical class | Group | Formula | Structural Formula | Prefix | Suffix | Example |
|---|---|---|---|---|---|---|
| Phosphine | Phosphino | R3P | ) | phosphino- | -phosphane | ){kind=small} Methylpropylphosphane |
| Phosphodiester | Phosphate | HOPO(OR)2 | ) | phosphoric acid di(substituent) ester | di(substituent) hydrogenphosphate | DNA |
| Phosphonic acid | Phosphono | RP(=O)(OH)2 | ) | phosphono- | substituent phosphonic acid | ){kind=small} Benzylphosphonic acid |
| Phosphate | Phosphate | ROP(=O)(OH)2 | ) | phospho- | ){kind=small} Glyceraldehyde 3-phosphate | |
| Sulfide or thioether | RSR' | ){kind=small} | di(substituent) sulfide | ){kind=small} Dimethyl sulfide | ||
| Sulfone | Sulfonyl | RSO2R' | ) | sulfonyl- | di(substituent) sulfone | ) Dimethyl sulfone (Methylsulfonylmethane) |
| Sulfonic acid | Sulfo | RSO3H | ) | sulfo- | substituent sulfonic acid | ) Benzenesulfonic acid |
| Sulfoxide | Sulfinyl | RSOR' | ) | sulfinyl- | di(substituent) sulfoxide | ) Diphenyl sulfoxide |
| Thiol | Sulfhydryl | RSH | ) | mercapto-, sulfanyl- | -thiol | ){kind=small} Ethanethiol (Ethyl mercaptan) |
| Thiocyanate | Thiocyanate | RSCN | ){kind=small} | thiocyanato- | alkyl thiocyanate | |
| Disulfide | Disulfide | RSSR' | ){kind=small} | alkyl alkyl disulfide | ) Diphenyl disulfide Diphenyl disulfide 1,2-diphenyldisulfane |
Other
- Methyl
- Methylene
- Ethyl
- Propyl
- Butyl
- Hydroxy
- Methoxy
- Hydroxymethyl
- Methylenedioxy
- Phenyl
- Acetyl
- Acetoxy
- Thioamide
- Thioester
- Thioketone
See also
- Compendium of Chemical Terminology (IUPAC "Gold Book")
External links
Functional group |
|---|
| Chemical class: Alcohol • Aldehyde • Alkane • Alkene • Alkyne • Amide • Amine • Azo compound • Benzene derivative • Carboxylic acid • Cyanate • Disulfide • Ester • Ether • Haloalkane • Imine • Isocyanide • Isocyanate • Ketone • Nitrile • Nitro compound • Nitroso compound • Peroxide • Phosphoric acid • Pyridine derivative • Sulfone • Sulfonic acid • Sulfoxide • Thioester • Thioether • Thiol |
Concepts in organic chemistry |
|---|
| Aromaticity, Covalent bonding, Functional groups, Nomenclature, Organic compounds, Organic reactions, Organic synthesis, Publications, Spectroscopy, Stereochemistry, List of organic compounds |
Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may
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atom (Greek ἄτομος or átomos meaning "indivisible") is the smallest particle still characterizing a chemical element.
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molecule is defined as a sufficiently stable electrically neutral group of at least two atoms in a definite arrangement held together by strong chemical bonds.[1][2] In organic chemistry and biochemistry, the term molecule
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chemical reaction is a process that results in the interconversion of chemical substances.[1] The substance or substances initially involved in a chemical reaction are called reactants.
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Alkanes, also known as Paraffins, are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i.e. hydrocarbons), where each of these atoms are linked together exclusively by single bonds (i.e. they are saturated compounds) without any cyclic structure (i.
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systematic names have been created.
These can be as simple as assigning a prefix and a number to each object (in which case they are a type of numbering scheme), or as complex as encoding the complete structure of the object in the name.
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These can be as simple as assigning a prefix and a number to each object (in which case they are a type of numbering scheme), or as complex as encoding the complete structure of the object in the name.
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organic compounds]] An organic compound is any member of a large class of chemical compounds whose molecules contain carbon; for historical reasons discussed below, a few types of compounds such as carbonates, carbon oxides and cyanides, as well as elemental carbon are
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Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or between atoms and other covalent bonds.
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polyatomic ion is a molecule that bears ionic groups, that is, a molecule with a charge. The majority of biological compounds and inorganic species conform to this strict definition.
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complex in chemistry usually is used to describe molecules or ensembles formed by the combination of ligands and metal ions. Originally, a complex implied a reversible association of molecules, atoms, or ions through weak chemical bonds.
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radicals (often referred to as free radicals) are atomic or molecular species with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly reactive, so radicals are likely to take part in chemical reactions.
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radicals (often referred to as free radicals) are atomic or molecular species with unpaired electrons on an otherwise open shell configuration. These unpaired electrons are usually highly reactive, so radicals are likely to take part in chemical reactions.
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1
Atomic radius 70 pm
Atomic radius (calc.
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(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1
Atomic radius 70 pm
Atomic radius (calc.
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The alpha carbon in organic chemistry refers to the first carbon after the carbon that attaches to the functional group (the carbon is attached at the first, or alpha, position).
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hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "Pure" hydrocarbons, whereas
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side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. An R group is a generic label for a side chain which can be anything; however, it is typically stable and covalently linked to the adjoining atom.
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Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classifications depend to a certain degree on
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Alkanes, also known as Paraffins, are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i.e. hydrocarbons), where each of these atoms are linked together exclusively by single bonds (i.e. they are saturated compounds) without any cyclic structure (i.
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An alkyl is a univalent (or free) radical containing only carbon and hydrogen atoms arranged in a chain. The alkyls form a homologous series with the general formula CnH2n+1.
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Methane is a chemical compound with the molecular formula CH4. It is the simplest alkane, and the principal component of natural gas. Methane's bond angles are 109.
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alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond. The simplest alkenes, with only one double bond and no other functional groups, form a homologous series of hydrocarbons with the general formula
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alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond. The simplest alkenes, with only one double bond and no other functional groups, form a homologous series of hydrocarbons with the general formula
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Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a double bond, ethylene is called an unsaturated hydrocarbon or an olefin.
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Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene
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Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene
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Acetylene (systematic name: ethyne) is a hydrocarbon belonging to the group of alkynes. It is considered to be the simplest of all alkynes as it consists of two hydrogen atoms and two carbon atoms.
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Benzene, or Benzol (see also Benzine) is an organic chemical compound with the formula C6H6. It is sometimes abbreviated Ph–H. Benzene is a colorless and inflammable liquid with a sweet smell and a relatively high melting point.
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In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula
where the six carbon atoms are arranged in a cyclic ring structure. It is in the Aryl group.
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- -C6H5
where the six carbon atoms are arranged in a cyclic ring structure. It is in the Aryl group.
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Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C.
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Toluene, also known as methylbenzene or phenylmethane, is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene.
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