Organic compound - Wikipedia [Link]
org/wiki/Organic_compound
Organic compound
Organic compounds are a subclass of chemical compounds of
carbon. Little consensus exists among chemists on the exact
definition of organic compound;[1] the only universally accepted
definition is the quasi-tautological "organic compounds are the
subject matter of organic chemistry".
Generally, any large chemical compound containing a carbon–
hydrogen or carbon–carbon bond is accepted as an organic
compound. Thus alkanes (e.g. ethane, CH3−CH3) and their
derivatives are typically considered organic. For historical and
disciplinary reasons, small molecules containing carbon are
− Methane (CH4) is among the
generally not accepted: cyanide ion (CN ), hydrogen cyanide
simplest organic compounds.
(HCN), chloroformic acid (ClCO2H), carbon dioxide (CO2), and
2−
carbonate ion (CO3 ) may all be excluded.[1] Because of carbon's
ability to catenate (form chains with other carbon atoms), millions of organic compounds are
known.[1]
Although organic compounds make up only a small percentage of Earth's crust, they are of central
importance because all known life is based on organic compounds. Living things incorporate
inorganic carbon compounds into organic compounds through a network of processes (the carbon
cycle) that convert carbon dioxide and a hydrogen source like water into simple sugars and other
organic molecules.
In the chemical industry, synthetic organic compounds are ultimately derived from
petrochemicals, mainly hydrocarbons. Petrochemicals are themselves formed from the geologic
degradation of biological matter at high pressures and temperatures underground.[2]
Historically, organic compounds were defined as compounds originating in living things, an
expression of early-modern scientific vitalism. As vitalism became increasingly untenable, organic
chemistry broadened its scope to study all large molecules; at the time, all known large molecules
contained carbon. Organic molecules discovered in biological contexts are now known as natural
products. In the 20th century, chemists discovered new large molecular species amongst the metal
complexes. Such objects are not admitted into general organic chemistry unless they also contain
carbon; otherwise their study is a new and separate field, metalorganic chemistry.
In chemical nomenclature, an organyl group, frequently represented by the letter R, refers to any
monovalent substituent whose open valence is on a carbon atom.[3]
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Definition
For historical reasons discussed below, a few types of carbon-containing compounds, such as
carbides, carbonates (excluding carbonate esters), simple oxides of carbon (for example, CO and
CO2) and cyanides are generally considered inorganic compounds. Different forms (allotropes) of
pure carbon, such as diamond, graphite, fullerenes and carbon nanotubes[4] are also excluded
because they are simple substances composed of a single element and so not generally considered
chemical compounds. The word "organic" in this context does not mean "natural".[5]
History
Vitalism
Vitalism was a widespread conception that substances found in organic nature are formed from the
chemical elements by the action of a "vital force"[6] or "life-force" (vis vitalis) that only living
organisms possess.[7]
In the 1810s, Jöns Jacob Berzelius argued that a regulative force must exist within living bodies.
Berzelius also contended that compounds could be distinguished by whether they required any
organisms in their synthesis (organic compounds) or whether they did not (inorganic compounds).
[8] Vitalism taught that formation of these "organic" compounds were fundamentally different from
the "inorganic" compounds that could be obtained from the elements by chemical manipulations in
laboratories.[9][10]
Vitalism survived for a short period after the formulation of modern ideas about the atomic theory
and chemical elements. It first came under question in 1824, when Friedrich Wöhler synthesized
oxalic acid, a compound known to occur only in living organisms, from cyanogen. A further
experiment was Wöhler's 1828 synthesis of urea from the inorganic salts potassium cyanate and
ammonium sulfate. Urea had long been considered an "organic" compound, as it was known to
occur only in the urine of living organisms. Wöhler's experiments were followed by many others, in
which increasingly complex "organic" substances were produced from "inorganic" ones without the
involvement of any living organism, thus disproving vitalism.[11]
Modern classification and ambiguities
Although vitalism has been discredited, scientific nomenclature retains the distinction between
organic and inorganic compounds. The modern meaning of organic compound is any compound
that contains a significant amount of carbon—even though many of the organic compounds known
today have no connection to any substance found in living organisms. The term carbogenic has
been proposed by E. J. Corey as a modern alternative to organic, but this neologism remains
relatively obscure.[12]
As described in detail below, any definition of organic compound that uses simple, broadly-
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applicable criteria turns out to be unsatisfactory, to varying
degrees. The modern, commonly accepted definition of organic
compound essentially amounts to any carbon-containing
compound, excluding several classes of substances traditionally
considered "inorganic". The list of substances so excluded varies
from author to author. Still, it is generally agreed upon that there
are (at least) a few carbon-containing compounds that should not
be considered organic. For instance, almost all authorities would
require the exclusion of alloys that contain carbon, including steel
(which contains cementite, Fe3C), as well as other metal and
semimetal carbides (including "ionic" carbides, e.g., Al4C3 and The L-isoleucine molecule,
CaC2 and "covalent" carbides, e.g. B4C and SiC, and graphite C6H13NO2, showing features
intercalation compounds, e.g. KC8). Other compounds and typical of organic compounds.
Carbon atoms are in black,
materials that are considered 'inorganic' by most authorities
hydrogens gray, oxygens red,
include: metal carbonates, simple oxides of carbon (CO, CO2, and
and nitrogen blue.
arguably, C3O2), the allotropes of carbon, cyanide derivatives not
containing an organic residue (e.g., KCN, (CN)2, BrCN, cyanate
− −
anion OCN , etc.), and heavier analogs thereof (e.g., cyaphide anion CP , CSe2, COS; although
carbon disulfide CS2 is often classed as an organic solvent). Halides of carbon without hydrogen
(e.g., CF4 and CClF3), phosgene (COCl2), carboranes, metal carbonyls (e.g., nickel tetracarbonyl),
mellitic anhydride (C12O9), and other exotic oxocarbons are also considered inorganic by some
authorities.
Nickel tetracarbonyl (Ni(CO)4) and other metal carbonyls are often volatile liquids, like many
organic compounds, yet they contain only carbon bonded to a transition metal and to oxygen, and
are often prepared directly from metal and carbon monoxide. Nickel tetracarbonyl is typically
classified as an organometallic compound as it satisfies the broad definition that organometallic
chemistry covers all compounds that contain at least one carbon to metal covalent bond; it is
unknown whether organometallic compounds form a subset of organic compounds. For example,
the evidence of covalent Fe-C bonding in cementite,[13] a major component of steel, places it within
this broad definition of organometallic, yet steel and other carbon-containing alloys are seldom
regarded as organic compounds. Thus, it is unclear whether the definition of organometallic should
be narrowed, whether these considerations imply that organometallic compounds are not
necessarily organic, or both.
Metal complexes with organic ligands but no carbon-metal bonds (e.g., (CH3CO2)2Cu) are not
considered organometallic; instead, they are called metal-organic compounds (and might be
considered organic).
The relatively narrow definition of organic compounds as those containing C–H bonds excludes
compounds that are (historically and practically) considered organic. Neither urea CO(NH2)2 nor
oxalic acid (COOH)2 are organic by this definition, yet they were two key compounds in the
vitalism debate. However, the IUPAC Blue Book on organic nomenclature specifically mentions
urea[14] and oxalic acid[15] as organic compounds. Other compounds lacking C–H bonds but
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traditionally considered organic include benzenehexol, mesoxalic acid, and carbon tetrachloride.
Mellitic acid, which contains no C–H bonds, is considered a possible organic compound in Martian
soil.[16] Terrestrially, it, and its anhydride, mellitic anhydride, are associated with the mineral
mellite (Al2C6(COO)6·16H2O).
A slightly broader definition of the organic compound includes all compounds bearing C–H or C–C
bonds. This would still exclude urea. Moreover, this definition still leads to somewhat arbitrary
divisions in sets of carbon-halogen compounds. For example, CF4 and CCl4 would be considered by
this rule to be "inorganic", whereas CHF3, CHCl3, and C2Cl6 would be organic, though these
compounds share many physical and chemical properties.
Classification
Organic compounds may be classified in a variety of ways. One major distinction is between
natural and synthetic compounds. Organic compounds can also be classified or subdivided by the
presence of heteroatoms, e.g., organometallic compounds, which feature bonds between carbon
and a metal, and organophosphorus compounds, which feature bonds between carbon and a
phosphorus.
Another distinction, based on the size of organic compounds, distinguishes between small
molecules and polymers.
Natural compounds
Natural compounds refer to those that are produced by plants or animals. Many of these are still
extracted from natural sources because they would be more expensive to produce artificially.
Examples include most sugars, some alkaloids and terpenoids, certain nutrients such as vitamin
B12, and, in general, those natural products with large or stereoisometrically complicated
molecules present in reasonable concentrations in living organisms.
Further compounds of prime importance in biochemistry are antigens, carbohydrates, enzymes,
hormones, lipids and fatty acids, neurotransmitters, nucleic acids, proteins, peptides and amino
acids, lectins, vitamins, and fats and oils.
Synthetic compounds
Compounds that are prepared by reaction of other compounds are known as "synthetic". They may
be either compounds that are already found in plants/animals or those artificial compounds that
do not occur naturally.
Most polymers (a category that includes all plastics and rubbers) are organic synthetic or semi-
synthetic compounds.
Biotechnology
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Many organic compounds—two examples are ethanol and insulin—are manufactured industrially
using organisms such as bacteria and yeast.[17] Typically, the DNA of an organism is altered to
express compounds not ordinarily produced by the organism. Many such biotechnology-
engineered compounds did not previously exist in nature.[18]
Databases
▪ The CAS database is the most comprehensive repository for data on organic compounds. The
search tool SciFinder is offered.
▪ The Beilstein database contains information on 9.8 million substances, covers the scientific
literature from 1771 to the present, and is today accessible via Reaxys. Structures and a large
diversity of physical and chemical properties are available for each substance, with reference
to original literature.
▪ PubChem contains 18.4 million entries on compounds and especially covers the field of
medicinal chemistry.
A great number of more specialized databases exist for diverse branches of organic chemistry.[19]
Structure determination
The main tools are proton and carbon-13 NMR spectroscopy, IR spectroscopy, mass spectrometry,
UV-Vis spectroscopy and X-ray crystallography.[20]
See also
▪ List of chemical compounds
▪ List of organic compounds
▪ Organometallic chemistry – Study of organic compounds containing metal(s)
▪ Inorganic compound – Chemical compound without any carbon-hydrogen bonds
References
1. Seager, Spencer L.; Slabaugh, Michael R. (2004). Chemistry for Today: General, Organic, and
Biochemistry. Thomson Brooks/Cole. p. 342. ISBN 9780534399696. OCLC 155910842 (https://
[Link]/oclc/155910842).
2. Smith, Cory. "Petrochemicals" ([Link] American Fuel &
Petrochemical Manufacturers. Archived ([Link]
[Link]/industries/products/petrochemicals) from the original on 11 September 2021.
Retrieved 18 December 2016.
3. IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online
version: (2006–) "Organyl groups ([Link]
doi:10.1351/goldbook.O04329 ([Link]
5 of 7 29-04-2026, 19:49
Organic compound - Wikipedia [Link]
4. Fullerene derivatives are more frequently considered organic, and fullerene chemistry is
usually considered a branch of organic chemistry. The methods of organic synthesis have been
applied to the rational synthesis of fullerenes and carbon nanotubes.
5. "Organic Chemistry" ([Link]
[Link]). Archived ([Link]
[Link]/content/acs/en/careers/chemical-sciences/areas/[Link]) from the original
on 2022-09-16. Retrieved 2022-08-25.
6. "Life Force, Naturalism & Holism" ([Link] Encyclopedia
Britannica. July 20, 1998. Retrieved March 10, 2024.
7. Naylor, R. L.; Martin, J. D.; Staley, R. (2023). "Vital Physics" ([Link] Physics in
Perspective. 25 (1–2): 1–2. Bibcode:2023PhP....25....1N ([Link]
3PhP....25....1N). doi:10.1007/s00016-023-00297-z ([Link]
297-z). Retrieved 2024-03-10.
8. Wilkinson, Ian (2002-06-10). "History of Clinical Chemistry" ([Link]
articles/PMC6208063). EJIFCC. 13 (4): 114–118. ISSN 1650-3414 ([Link]
issn/1650-3414). PMC 6208063 ([Link]
9. Coulter, Ian; Snider, Pamela; Neil, Amy (June 2019). "Vitalism–A Worldview Revisited: A
Critique Of Vitalism And Its Implications For Integrative Medicine" ([Link]
v/pmc/articles/PMC7217401). Integrative Medicine: A Clinician's Journal. 18 (3): 60–73.
PMC 7217401 ([Link] PMID 32549817 (http
s://[Link]/32549817).
10. "Vitalism: Physiological Chemistry" ([Link]
v-1/sections/physiological-chemistry). Routledge Encyclopedia of Philosophy. March 10, 2024.
Retrieved March 10, 2024.
11. Leicester, Henry Marshall; Klickstein, Herbert S. (1951). A Source Book in Chemistry,
1400-1900 ([Link]
Harvard University Press. p. 309.
12. Corey, E. J.; Cheng, Xue-Min (1989). The Logic of Chemical Synthesis ([Link]
[Link]/25/items/Logic_of_Chemical_Synthesis_Corey_1989/Logic_of_Chemical_Synthesis_
Corey_1989_text.pdf) (PDF). Wiley. ISBN 9780471509790. p. 1: "The words carbogen and
carbogenic can be regarded as synonymous with the traditional terms organic compound and
organic. Despite habit and history, the authors are not comfortable with the logic of several
common chemical usages of organic, for example organic synthesis."
13. Jiang, C.; Srinivasan, S. G.; Caro, A.; Maloy, S. A. (2008). "Structural, elastic, and electronic
properties of Fe3C from first principles". Journal of Applied Physics. 103 (4): 043502–043502–
8. arXiv:0711.1528 ([Link] Bibcode:2008JAP...103d3502J ([Link]
[Link]/abs/2008JAP...103d3502J). doi:10.1063/1.2884529 ([Link]
63%2F1.2884529). S2CID 94576016 ([Link]
14. "IUPAC Blue Book, Urea and Its Derivatives Rule C-971" ([Link]
nclature/79/r79_661.htm). Archived ([Link]
[Link]/iupac/nomenclature/79/r79_661.htm) from the original on 2021-05-06.
Retrieved 2009-11-22.
15. "IUPAC Blue Book, Table 28(a) Carboxylic acids and related groups. Unsubstituted parent
structures" ([Link] Archived ([Link]
[Link]/web/20210628213602/[Link]
[Link]) from the original on 2021-06-28. Retrieved 2009-11-22.
6 of 7 29-04-2026, 19:49
Organic compound - Wikipedia [Link]
16. S. A. Benner; K. G. Devine; L. N. Matveeva; D. H. Powell (2000). "The missing organic
molecules on Mars" ([Link] Proceedings of the
National Academy of Sciences. 97 (6): 2425–2430. Bibcode:2000PNAS...97.2425B ([Link]
[Link]/abs/2000PNAS...97.2425B). doi:10.1073/pnas.040539497 ([Link]
0.1073%2Fpnas.040539497). PMC 15945 ([Link]
45). PMID 10706606 ([Link]
17. Korpi, Anne; Järnberg, Jill; Pasanen, Anna-Liisa (2009). "Microbial volatile organic
compounds". Critical Reviews in Toxicology. 39 (2): 139–193.
doi:10.1080/10408440802291497 ([Link]
ISSN 1547-6898 ([Link] PMID 19204852 ([Link]
[Link]/19204852). S2CID 98688955 ([Link]
88955).
18. Durland, Justin; Ahmadian-Moghadam, Hamid (2022), "Genetics, Mutagenesis" ([Link]
[Link]/books/NBK560519/), StatPearls, Treasure Island (FL): StatPearls Publishing,
PMID 32809354 ([Link] archived ([Link]
g/web/20230709193155/[Link] from the original on
2023-07-09, retrieved 2023-01-04
19. Borysov, Stanislav S.; Geilhufe, R. Matthias; Balatsky, Alexander V. (2017-02-09). "Organic
materials database: An open-access online database for data mining" ([Link]
[Link]/pmc/articles/PMC5300202). PLOS ONE. 12 (2) e0171501.
Bibcode:2017PLoSO..1271501B ([Link]
doi:10.1371/[Link].0171501 ([Link]
ISSN 1932-6203 ([Link] PMC 5300202 ([Link]
[Link]/pmc/articles/PMC5300202). PMID 28182744 ([Link]
182744).
20. Ernö Pretsch, Philippe Bühlmann, Martin Badertscher (2009), Structure Determination of
Organic Compounds (Fourth, Revised and Enlarged Edition). Springer-Verlag Berlin
Heidelberg
External links
▪ Organic Compounds Database ([Link]
▪ Organic Materials Database ([Link]
Retrieved from "[Link]
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