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Organic chemistry is a branch of
chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during a with other . ...

chemistry
that studies the structure, properties and reactions of
organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
s, which contain
carbon Carbon (from la, carbo "coal") is a with the C and 6. It is lic and —making four s available to form s. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three occur naturally, ...

carbon
in
covalent bonding A covalent bond is a chemical bond A chemical bond is a lasting attraction between atoms, ions or molecules that enables the formation of chemical compounds. The bond may result from the Coulomb's law, electrostatic force of attraction bet ...
.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their
structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bondi ...
. Study of properties includes
physical Physical may refer to: *Physical examination, a regular overall check-up with a doctor *Physical (album), ''Physical'' (album), a 1981 album by Olivia Newton-John **Physical (Olivia Newton-John song), "Physical" (Olivia Newton-John song) *Physical ( ...
and
chemical properties A chemical property is any of a material's properties that becomes evident during, or after, a chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substance A chemical substan ...
, and evaluation of
chemical reactivity In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they under ...
to understand their behavior. The study of
organic reaction Organic reactions are s involving s. The basic reaction types are s, s, s, s, s, and . In , organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, , , depend on organic re ...
s includes the
chemical synthesis As a topic of , chemical synthesis (or combination) is the artificial execution of s to obtain one or several s. This occurs by and chemical manipulations usually involving one or more reactions. In modern uses, the process is and reliable. A ...

chemical synthesis
of
natural product A natural product is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together b ...
s,
drug Uncoated tablets, consisting of about 90% acetylsalicylic acid, along with a minor amount of inert fillers and binders. Aspirin is a pharmaceutical drug A medication (also referred to as medicine, pharmaceutical drug, medicinal drug or s ...

drug
s, and
polymer A polymer (; Greek ''poly- Poly, from the Greek :wikt:πολύς, πολύς meaning "many" or "much", may refer to: Businesses * China Poly Group Corporation, a Chinese business group, and its subsidiaries: ** Poly Property, a Hong Kong inc ...

polymer
s, and study of individual organic molecules in the laboratory and via theoretical (
in silico In biology Biology is the natural science that studies life and living organisms, including their anatomy, physical structure, Biochemistry, chemical processes, Molecular biology, molecular interactions, Physiology, physiological mechanisms ...
) study. The range of chemicals studied in organic chemistry includes
hydrocarbon In , a hydrocarbon is an consisting entirely of and . Hydrocarbons are examples of s. Hydrocarbons are generally colourless and hydrophobic with only weak odours. Because of their diverse molecular structures, it is difficult to generalize furth ...
s (compounds containing only
carbon Carbon (from la, carbo "coal") is a with the C and 6. It is lic and —making four s available to form s. It belongs to group 14 of the periodic table. Carbon makes up only about 0.025 percent of Earth's crust. Three occur naturally, ...

carbon
and
hydrogen Hydrogen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance consisting only of atoms that all have the same ...

hydrogen
) as well as compounds based on carbon, but also containing other elements, especially
oxygen Oxygen is the chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance consisting only of atoms that all have the same ...

oxygen
,
nitrogen Nitrogen is the chemical element upright=1.0, 500px, The chemical elements ordered by link=Periodic table In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science ...

nitrogen
,
sulfur Sulfur (in nontechnical British English: sulphur) is a with the  S and  16. It is , and lic. Under , sulfur atoms form cyclic octatomic molecules with a chemical formula . Elemental sulfur is a bright yellow, line solid at . Sul ...

sulfur
,
phosphorus Phosphorus is a chemical element with the Symbol (chemistry), symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly Reactivity (chemistry), reactive, phosphor ...

phosphorus
(included in many
biochemicals Biochemistry or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...
) and the
halogen The halogens () are a group A group is a number A number is a mathematical object used to counting, count, measurement, measure, and nominal number, label. The original examples are the natural numbers 1, 2, 3, 4, and so forth. Numbers can b ...

halogen
s.
Organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and s ...
is the study of compounds containing carbon–
metal A metal (from Greek#REDIRECT Greek Greek may refer to: Greece Anything of, from, or related to Greece Greece ( el, Ελλάδα, , ), officially the Hellenic Republic, is a country located in Southeast Europe. Its population is appro ...

metal
bonds. In addition, contemporary research focuses on organic chemistry involving other
organometallic Organometallic chemistry is the study of organometallic compounds, chemical compound A chemical compound is a chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is any subst ...
s including the
lanthanide The lanthanide () or lanthanoid () series of chemical elements comprises the 15 metallic chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an elem ...
s, but especially the
transition metal In chemistry, the term transition metal (or transition element) has three possible definitions: * The IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations tha ...
s zinc, copper, palladium, nickel, cobalt, titanium and chromium. Organic compounds form the basis of all earthly life and constitute the majority of known chemicals. The bonding patterns of carbon, with its valence of four—formal single, double, and triple bonds, plus structures with delocalized electrons—make the array of organic compounds structurally diverse, and their range of applications enormous. They form the basis of, or are constituents of, many commercial products including
pharmaceuticals A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to medical diagnosis, diagnose, cure, therapy, treat, or preventive medicine, prevent disease. Drug therapy (pharmacotherapy) ...

pharmaceuticals
;
petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum Petroleum (), also known as crude oil and oil, is a #Latent heat of vaporization, naturally occurring, yellowish-black liquid found in geolo ...
s and
agrichemical An agrochemical or agrichemical, a contraction of ''agricultural chemical'', is a chemical A chemical substance is a form of matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by ha ...
s, and products made from them including
lubricants A lubricant is a substance that helps to reduce friction Friction is the force In physics Physics (from grc, φυσική (ἐπιστήμη), physikḗ (epistḗmē), knowledge of nature, from ''phýsis'' 'nature'), , is th ...
,
solvents A solvent (from the Latin Latin (, or , ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken in the area around Rome, known as Latium. Through the power of the ...
;
plastic Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. Synthetic may also refer to: In the sense of both "combination" and "artificial" * Synthetic chemical or s ...

plastic
s;
fuels A fuel is any material that can be made to react with other substances so that it releases energy as thermal energy Thermal radiation in visible light can be seen on this hot metalwork. Thermal energy refers to several distinct physical conc ...
and
explosives An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion An explosion is a rapid expansion in volume associated with an extremely vigorous outward release o ...
. The study of organic chemistry overlaps
organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and s ...
and
biochemistry Biochemistry or biological chemistry, is the study of es within and relating to living s. A sub-discipline of both and , biochemistry may be divided into three fields: , and . Over the last decades of the 20th century, biochemistry has beco ...

biochemistry
, but also with
medicinal chemistry Medicinal chemistry is discipline at the intersection of chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter ...
,
polymer chemistry Polymer chemistry is a sub-discipline of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior ...
, and
materials science The interdisciplinary Interdisciplinarity or interdisciplinary studies involves the combination of two or more academic discipline An academic discipline or academic field is a subdivision of knowledge that is Education, taught and resea ...
.


History

Before the 18th century, chemists generally believed that compounds obtained from living organisms were endowed with a vital force that distinguished them from
inorganic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during a ...
s. According to the concept of
vitalism Vitalism is the belief that "living organisms are fundamentally different from non-living entities because they contain some non-physical element or are governed by different principles than are inanimate things". Where vitalism explicitly invoke ...
(vital force theory), organic matter was endowed with a "vital force". During the first half of the nineteenth century, some of the first systematic studies of organic compounds were reported. Around 1816 started a study of
soap Soap is a salt (chemistry), salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, ...

soap
s made from various
fat In nutrition Nutrition is the biochemical Biochemistry or biological chemistry, is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided ...

fat
s and
alkali In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds composed of ato ...

alkali
s. He separated the acids that, in combination with the alkali, produced the soap. Since these were all individual compounds, he demonstrated that it was possible to make a chemical change in various fats (which traditionally come from organic sources), producing new compounds, without "vital force". In 1828
Friedrich Wöhler Friedrich Wöhler () FRS(For) HFRSE Fellowship of the Royal Society of Edinburgh (FRSE) is an award granted to individuals that the Royal Society of Edinburgh, Scotland's national academy of science and Literature, letters, judged to be "em ...

Friedrich Wöhler
produced the ''organic'' chemical
urea Urea, also known as carbamide, is an organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the prop ...

urea
(carbamide), a constituent of
urine Urine is a liquid by-product A by-product or byproduct is a secondary product derived from a production process, process or ; it is not the primary product or service being produced. A by-product can be useful and marketable or it can be cons ...

urine
, from ''inorganic'' starting materials (the salts potassium cyanate and
ammonium sulfate Ammonium sulfate (American English and international scientific usage; ammonium sulphate in British English British English (BrE) is the standard dialect of the English language English is a West Germanic languages, West Germanic lan ...

ammonium sulfate
), in what is now called the
Wöhler synthesis The Wöhler synthesis is the conversion of ammonium cyanate Ammonium cyanate is an inorganic compound In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds, that is, a compound that is not an org ...
. Although Wöhler himself was cautious about claiming he had disproved vitalism, this was the first time a substance thought to be organic was synthesized in the laboratory without biological (organic) starting materials. The event is now generally accepted as indeed disproving the doctrine of vitalism. In 1856
William Henry Perkin Sir William Henry Perkin (12 March 1838 – 14 July 1907) was a British chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist A scientist is a person who conducts Scien ...
, while trying to manufacture
quinine Quinine is a medication used to treat malaria Malaria is a mosquito-borne infectious disease that affects humans and other animals. Malaria causes symptoms Signs and symptoms are the observed or detectable signs, and experienced sympto ...

quinine
accidentally produced the organic
dye A dye is a color Color (American English) or colour (Commonwealth English) is the visual perception, visual perceptual Physical property, property corresponding in humans to the categories called ''blue'', ''green'', ''red'', etc. Colo ...
now known as Perkin's mauve. His discovery, made widely known through its financial success, greatly increased interest in organic chemistry. A crucial breakthrough for organic chemistry was the concept of chemical structure, developed independently in 1858 by both
Friedrich August KekuléFriedrich may refer to: Names *Friedrich (surname)Friedrich or Friedrichs is a German people, German surname. Notable people with the surname include: Friedrich * Johannes Friedrich, Bishop of the Evangelical Lutheran Church in Bavaria * Ariane F ...
and Archibald Scott Couper. Both researchers suggested that
tetravalent In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, properties, behavior and the changes they und ...
carbon atoms could link to each other to form a carbon lattice, and that the detailed patterns of atomic bonding could be discerned by skillful interpretations of appropriate chemical reactions. The era of the
pharmaceutical A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to medical diagnosis, diagnose, cure, therapy, treat, or preventive medicine, prevent disease. Drug therapy (pharmacotherapy) ...
industry began in the last decade of the 19th century when the manufacturing of acetylsalicylic acidmore commonly referred to as
aspirin Aspirin, also known as acetylsalicylic acid (ASA), is a medication A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug Uncoated tablets, consisting of about 90% acetylsalicy ...

aspirin
in Germany was started by
Bayer Bayer Aktiengesellschaft, AG (; ) is a German multinational corporation, multinational pharmaceutical company, pharmaceutical and life sciences company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, ...

Bayer
. By 1910
Paul Ehrlich Paul Ehrlich (; 14 March 1854 – 20 August 1915) was a Nobel Prize-winning German physician and scientist who worked in the fields of hematology, immunology, and antimicrobial chemotherapy. Among his foremost achievements were finding a cure fo ...

Paul Ehrlich
and his laboratory group began developing arsenic-based
arsphenamine Arsphenamine, also known as Salvarsan or compound 606, is a drug Uncoated tablets, consisting of about 90% acetylsalicylic acid, along with a minor amount of inert fillers and binders. Aspirin is a pharmaceutical drug A medication (als ...
, (Salvarsan), as the first effective medicinal treatment of
syphilis Syphilis is a sexually transmitted infection Sexually transmitted infections (STIs), also referred to as sexually transmitted diseases (STDs), are infection An infection is the invasion of an organism's body Tissue (biology), tissues ...
, and thereby initiated the medical practice of
chemotherapy Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment Cancer Cancer is a group of diseases involving abnormal cell growth with the potential to invade or Metastasis, spread to other parts o ...

chemotherapy
. Ehrlich popularized the concepts of "magic bullet" drugs and of systematically improving drug therapies. His laboratory made decisive contributions to developing antiserum for
diphtheria Diphtheria is an infection caused by the bacteria, bacterium ''Corynebacterium diphtheriae''. Most infections are asymptomatic or have a mild Course (medicine), clinical course, but in some outbreaks more than 10% of those diagnosed with the di ...

diphtheria
and standardizing therapeutic serums. Early examples of organic reactions and applications were often found because of a combination of luck and preparation for unexpected observations. The latter half of the 19th century however witnessed systematic studies of organic compounds. The development of synthetic indigo is illustrative. The production of indigo from plant sources dropped from 19,000 tons in 1897 to 1,000 tons by 1914 thanks to the synthetic methods developed by
Adolf von Baeyer Johann Friedrich Wilhelm Adolf von Baeyer (; 31 October 1835 – 20 August 1917) was a Germany, German chemist who synthesised indigo dye, indigo and developed a Von Baeyer nomenclature, nomenclature for cyclic compounds (that was subsequently ext ...
. In 2002, 17,000 tons of synthetic indigo were produced from
petrochemical Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum Petroleum (), also known as crude oil and oil, is a #Latent heat of vaporization, naturally occurring, yellowish-black liquid found in geolo ...
s.Steingruber, Elmar (2004) "Indigo and Indigo Colorants" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim. In the early part of the 20th century,
polymers A polymer (; Greek ''poly- Poly, from the Greek :wikt:πολύς, πολύς meaning "many" or "much", may refer to: Businesses * China Poly Group Corporation, a Chinese business group, and its subsidiaries: ** Poly Property, a Hong Kong inco ...

polymers
and
enzymes Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates int ...

enzymes
were shown to be large organic molecules, and petroleum was shown to be of biological origin. The multiple-step synthesis of complex organic compounds is called total synthesis.
Total synthesis Total synthesis is the complete chemical synthesis As a topic of chemistry, chemical synthesis (or combination) is the artificial execution of chemical reactions to obtain one or several product (chemistry), products. This occurs by physics, phy ...
of complex natural compounds increased in complexity to
glucose Glucose is a simple with the . Glucose is the most abundant , a subcategory of s. Glucose is mainly made by and most during from water and carbon dioxide, using energy from sunlight, where it is used to make in s, the most abundant carbohydr ...

glucose
and
terpineol Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group In organic chemistry, a functional group is a substituent or moiety in a molecule File:Pentacene on Ni(111 ...

terpineol
. For example,
cholesterol Cholesterol is any of a class of certain organic compound, organic molecules. A cholesterol is a sterol (or chemical modification, modified steroid), a type of lipid. Cholesterol is biosynthesis, biosynthesized by all animal Cell (biology)#Euk ...

cholesterol
-related compounds have opened ways to synthesize complex
human hormonesThe following is a list of hormones found in ''Homo sapiens''. Spelling is not uniform for many hormones. For example, current North American and international usage is estrogen, gonadotropin, while British usage retains the Greek digraph (orthograp ...
and their modified derivatives. Since the start of the 20th century, complexity of total syntheses has been increased to include molecules of high complexity such as
lysergic acid Lysergic acid, also known as -lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of ''Turbina corymbosa'' (ololiuhqui), ''Argyreia nervosa'' (Haw ...

lysergic acid
and . left, 230px, The total synthesis of vitamin B12 marked a major achievement in organic chemistry. The discovery of
petroleum Petroleum, also known as crude oil and oil, is a naturally occurring, yellowish-black liquid A liquid is a nearly incompressible In fluid mechanics or more generally continuum mechanics, incompressible flow (isochoric process, isoc ...

petroleum
and the development of the
petrochemical industry The petrochemical industry is concerned with the production and trade of petrochemicals Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum Petroleum (), also known as crude oil and oil, is a ...
spurred the development of organic chemistry. Converting individual petroleum compounds into ''types'' of compounds by various chemical processes led to
organic reactions ''Organic Reactions'' is a peer-reviewed book series that was established in 1942. It publishes detailed descriptions of useful organic reactions. Each article (called a chapter) is an Review article, invited review of the primary source material f ...
enabling a broad range of industrial and commercial products including, among (many) others:
plastics Plastics are a wide range of syntheticA synthetic is an artificial material produced by organic chemistry, organic chemical synthesis. Synthetic may also refer to: In the sense of both "combination" and "artificial" * Synthetic chemical or s ...

plastics
,
synthetic rubber A synthetic rubber is any artificial elastomer. They are polymers synthesized from petroleum byproducts. About 32-million metric tons of rubbers are produced annually in the United States, and of that amount two thirds are synthetic. Global revenue ...
, organic
adhesives Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantag ...
, and various property-modifying petroleum additives and
catalysts that utilizes a low-temperature oxidation catalyst to convert carbon monoxide to less toxic carbon dioxide Carbon dioxide (chemical formula ) is a colorless gas with a density about 53% higher than that of dry air. Carbon dioxide molecules ...

catalysts
. The majority of chemical compounds occurring in biological organisms are carbon compounds, so the association between organic chemistry and
biochemistry Biochemistry or biological chemistry, is the study of es within and relating to living s. A sub-discipline of both and , biochemistry may be divided into three fields: , and . Over the last decades of the 20th century, biochemistry has beco ...

biochemistry
is so close that biochemistry might be regarded as in essence a branch of organic chemistry. Although the history of biochemistry might be taken to span some four centuries, fundamental understanding of the field only began to develop in the late 19th century and the actual term ''biochemistry'' was coined around the start of 20th century. Research in the field increased throughout the twentieth century, without any indication of slackening in the rate of increase, as may be verified by inspection of abstraction and indexing services such as
BIOSIS Previews BIOSIS Previews is an English-language, bibliographic 250px, Bibliographies at the University Library of Graz Bibliography (from and ), as a discipline, is traditionally the academic study of books as physical, cultural objects; in this sen ...
and
Biological Abstracts Biological Abstracts is a database produced by Clarivate Analytics Clarivate is a company formed in 2016, following the acquisition of Thomson Reuters' Intellectual Property and Science Business by Onex Corporation and Baring Private Equity A ...
, which began in the 1920s as a single annual volume, but has grown so drastically that by the end of the 20th century it was only available to the everyday user as an online electronic
database In computing Computing is any goal-oriented activity requiring, benefiting from, or creating computing machinery. It includes the study and experimentation of algorithmic processes and development of both computer hardware , hardware and sof ...

database
.


Characterization

Since organic compounds often exist as
mixture In chemistry, a mixture is a material made up of two or more different chemical substances which are not chemically combined. A mixture is the physical combination of two or more substances in which the identities are retained and are mixed in th ...

mixture
s, a variety of techniques have also been developed to assess purity;
chromatography In chemical analysis, chromatography is a laboratory technique for the Separation process, separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it ...

chromatography
techniques are especially important for this application, and include
HPLC High-performance liquid chromatography (HPLC), formerly referred to as high-pressure liquid chromatography, is a technique in analytical chemistry Analytical chemistry studies and uses instruments and methods used to separate, identify, and ...

HPLC
and
gas chromatographyGas chromatography (GC) is a common type of chromatography Chromatography is a laboratory technique for the Separation process, separation of a mixture. The mixture is dissolved in a fluid (gas, solvent, water, ...) called the ''mobile phase,'' w ...
. Traditional methods of separation include
distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, ...

distillation
,
crystallization Crystallization or crystallisation is the process by which a solid Solid is one of the four fundamental states of matter (the others being liquid, gas and plasma). The molecules in a solid are closely packed together and contain the ...

crystallization
,
evaporation Evaporation is a type of that occurs on the of a as it changes into the gas phase. The surrounding gas must not be saturated with the evaporating substance. When the molecules of the liquid collide, they transfer energy to each other bas ...

evaporation
,
magnetic separation Magnetic separation is the process of separating components of mixtures by using magnets to attract magnetic materials.https://www.powderprocess.net/Equipments%20html/Magnets.html The process that is used for magnetic separation detaches non-magneti ...
and
solvent extraction A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical flui ...

solvent extraction
. Organic compounds were traditionally characterized by a variety of chemical tests, called "wet methods", but such tests have been largely displaced by spectroscopic or other computer-intensive methods of analysis. Listed in approximate order of utility, the chief analytical methods are: *
Nuclear magnetic resonance (NMR) spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a Spectroscopy, spectroscopic technique to observe local magnetic fields around Atomic nucleus, atomic nuclei. The sample ...
is the most commonly used technique, often permitting the complete assignment of atom connectivity and even stereochemistry using
correlation spectroscopyTwo-dimensional nuclear magnetic resonance spectroscopy (2D NMR) is a set of nuclear magnetic resonance spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a sp ...
. The principal constituent atoms of organic chemistry – hydrogen and carbon – exist naturally with NMR-responsive isotopes, respectively 1H and 13C. * Elemental analysis: A destructive method used to determine the elemental composition of a molecule. See also mass spectrometry, below. * Mass spectrometry indicates the molecular weight of a compound and, from the mass spectrum analysis, fragmentation patterns, its structure. High-resolution mass spectrometry can usually identify the exact formula of a compound and is used in place of elemental analysis. In former times, mass spectrometry was restricted to neutral molecules exhibiting some volatility, but advanced ionization techniques allow one to obtain the "mass spec" of virtually any organic compound. * Crystallography can be useful for determining molecular geometry when a single crystal of the material is available. Highly efficient hardware and software allows a structure to be determined within hours of obtaining a suitable crystal. Traditional spectroscopic methods such as infrared spectroscopy, optical rotation, and UV/VIS spectroscopy provide relatively nonspecific structural information but remain in use for specific applications. Refractive index and density can also be important for substance identification.


Properties

The physical properties of organic compounds typically of interest include both quantitative and qualitative features. Quantitative information includes a melting point, boiling point, and index of refraction. Qualitative properties include odor, consistency, solubility, and color.


Melting and boiling properties

Organic compounds typically melt and many boil. In contrast, while inorganic materials generally can be melted, many do not boil, and instead tend to degrade. In earlier times, the melting point (m.p.) and boiling point (b.p.) provided crucial information on the purity and identity of organic compounds. The melting and boiling points correlate with the polarity of the molecules and their molecular weight. Some organic compounds, especially symmetrical ones, Sublimation (phase transition), sublime. A well-known example of a sublimable organic compound is para-dichlorobenzene, the odiferous constituent of modern mothballs. Organic compounds are usually not very stable at temperatures above 300 °C, although some exceptions exist.


Solubility

Neutral organic compounds tend to be hydrophobic; that is, they are less soluble in water than in organic solvents. Exceptions include organic compounds that contain ionizable groups as well as low molecular weight alcohols, amines, and carboxylic acids where hydrogen bonding occurs. Otherwise, organic compounds tend to dissolve in organic solvents. Solubility varies widely with the organic solute and with the organic solvent.


Solid state properties

Various specialized properties of Molecular solid, molecular crystals and Polymer, organic polymers with conjugated systems are of interest depending on applications, e.g. thermo-mechanical and electro-mechanical such as piezoelectricity, electrical conductivity (see conductive polymers and organic semiconductors), and electro-optical (e.g. non-linear optics) properties. For historical reasons, such properties are mainly the subjects of the areas of polymer science and
materials science The interdisciplinary Interdisciplinarity or interdisciplinary studies involves the combination of two or more academic discipline An academic discipline or academic field is a subdivision of knowledge that is Education, taught and resea ...
.


Nomenclature

The names of organic compounds are either systematic, following logically from a set of rules, or nonsystematic, following various traditions. Systematic nomenclature is stipulated by specifications from IUPAC. Systematic nomenclature starts with the name for a parent structure within the molecule of interest. This parent name is then modified by prefixes, suffixes, and numbers to unambiguously convey the structure. Given that millions of organic compounds are known, rigorous use of systematic names can be cumbersome. Thus, IUPAC recommendations are more closely followed for simple compounds, but not complex molecules. To use the systematic naming, one must know the structures and names of the parent structures. Parent structures include unsubstituted hydrocarbons, heterocycles, and mono functionalized derivatives thereof. Nonsystematic nomenclature is simpler and unambiguous, at least to organic chemists. Nonsystematic names do not indicate the structure of the compound. They are common for complex molecules, which include most natural products. Thus, the informally named lysergic acid diethylamide is systematically named (6a''R'',9''R'')-''N'',''N''-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-''fg''] quinoline-9-carboxamide. With the increased use of computing, other naming methods have evolved that are intended to be interpreted by machines. Two popular formats are SMILES and InChI.


Structural drawings

Organic molecules are described more commonly by drawings or
structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bondi ...
s, combinations of drawings and chemical symbols. The Bond-line formula, line-angle formula is simple and unambiguous. In this system, the endpoints and intersections of each line represent one carbon, and hydrogen atoms can either be notated explicitly or assumed to be present as implied by Tetravalence, tetravalent carbon.


History

By 1880 an explosion in the number of chemical compounds being discovered occurred assisted by new synthetic and analytical techniques. Grignard described the situation as "chaos le plus complet" (complete chaos) due to the lack of convention it was possible to have multiple names for the same compound. This led to the creation of the Geneva Rules, Geneva rules in 1892.


Classification of organic compounds


Functional groups

The concept of functional groups is central in organic chemistry, both as a means to classify structures and for predicting properties. A functional group is a molecular module, and the reactivity of that functional group is assumed, within limits, to be the same in a variety of molecules. Functional groups can have a decisive influence on the chemical and physical properties of organic compounds. Molecules are classified based on their functional groups. Alcohols, for example, all have the subunit C-O-H. All alcohols tend to be somewhat hydrophile, hydrophilic, usually form esters, and usually can be converted to the corresponding halides. Most functional groups feature heteroatoms (atoms other than C and H). Organic compounds are classified according to functional groups, alcohols, carboxylic acids, amines, etc. Functional groups make the molecule more acidic or basic due to their electronic influence on surrounding parts of the molecule. As the Acid dissociation constant, pka (aka Base (chemistry), basicity) of the molecular addition/functional group increases, there is a corresponding dipole, when measured, increases in strength. A dipole directed towards the functional group (higher pka therefore basic nature of group) points towards it and decreases in strength with increasing distance. Dipole distance (measured in Angstrom, Angstroms) and Steric effects, steric hindrance towards the functional group have an intermolecular and intramolecular effect on the surrounding environment and pH level. Different functional groups have different pka values and bond strengths (single, double, triple) leading to increased electrophilicity with lower pka and increased nucleophile strength with higher pka. More basic/nucleophilic functional groups desire to attack an electrophilic functional group with a lower pka on another molecule (intermolecular) or within the same molecule (intramolecular). Any group with a net acidic pka that gets within range, such as an acyl or carbonyl group is fair game. Since the likelihood of being attacked decreases with an increase in pka, acyl chloride components with the lowest measured PKa, pka values are most likely to be attacked, followed by carboxylic acids (pka =4), thiols (13), malonates (13), alcohols (17), aldehydes (20), nitriles (25), esters (25), then amines (35). Amines are very basic, and are great nucleophiles/attackers.


Aliphatic compounds

The aliphatic hydrocarbons are subdivided into three groups of homologous series according to their state of Saturated and unsaturated compounds, saturation: * alkanes (paraffins): aliphatic hydrocarbons without any Double bond, double or triple bonds, i.e. just C-C, C-H single bonds * alkenes (olefins): aliphatic hydrocarbons that contain one or more double bonds, i.e. di-olefins (dienes) or poly-olefins. * alkynes (acetylenes): aliphatic hydrocarbons which have one or more triple bonds. The rest of the group is classified according to the functional groups present. Such compounds can be "straight-chain", branched-chain or cyclic. The degree of branching affects characteristics, such as the octane number or cetane number in petroleum chemistry. Both saturated (alicyclic) compounds and unsaturated compounds exist as cyclic derivatives. The most stable rings contain five or six carbon atoms, but large rings (macrocycles) and smaller rings are common. The smallest cycloalkane family is the three-membered cyclopropane ((CH2)3). Saturated cyclic compounds contain single bonds only, whereas aromatic rings have an alternating (or conjugated) double bond. Cycloalkanes do not contain multiple bonds, whereas the cycloalkenes and the cycloalkynes do.


Aromatic compounds

Aromatic hydrocarbons contain Conjugated system, conjugated double bonds. This means that every carbon atom in the ring is sp2 hybridized, allowing for added stability. The most important example is benzene, the structure of which was formulated by Friedrich August Kekulé von Stradonitz, Kekulé who first proposed the Delocalized electron, delocalization or Resonance (chemistry), resonance principle for explaining its structure. For "conventional" cyclic compounds, aromaticity is conferred by the presence of 4n + 2 delocalized pi electrons, where n is an integer. Particular instability (antiaromaticity) is conferred by the presence of 4n conjugated pi electrons.


Heterocyclic compounds

The characteristics of the cyclic hydrocarbons are again altered if heteroatoms are present, which can exist as either substituents attached externally to the ring (exocyclic) or as a member of the ring itself (endocyclic). In the case of the latter, the ring is termed a heterocycle. Pyridine and furan are examples of aromatic heterocycles while piperidine and tetrahydrofuran are the corresponding alicyclic heterocycles. The heteroatom of heterocyclic molecules is generally oxygen, sulfur, or nitrogen, with the latter being particularly common in biochemical systems. Heterocycles are commonly found in a wide range of products including aniline dyes and medicines. Additionally, they are prevalent in a wide range of biochemical compounds such as alkaloids, vitamins, steroids, and nucleic acids (e.g. DNA, RNA). Rings can fuse with other rings on an edge to give polycyclic compounds. The purine nucleoside bases are notable polycyclic aromatic heterocycles. Rings can also fuse on a "corner" such that one atom (almost always carbon) has two bonds going to one ring and two to another. Such compounds are termed spiro compound, spiro and are important in several
natural product A natural product is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together b ...
s.


Polymers

One important property of carbon is that it readily forms chains, or networks, that are linked by carbon-carbon (carbon-to-carbon) bonds. The linking process is called polymerization, while the chains, or networks, are called
polymer A polymer (; Greek ''poly- Poly, from the Greek :wikt:πολύς, πολύς meaning "many" or "much", may refer to: Businesses * China Poly Group Corporation, a Chinese business group, and its subsidiaries: ** Poly Property, a Hong Kong inc ...

polymer
s. The source compound is called a monomer. Two main groups of polymers exist synthetic polymers and biopolymers. Synthetic polymers are artificially manufactured, and are commonly referred to as plastic, industrial polymers."industrial polymers, chemistry of." Encyclopædia Britannica. 2006 Biopolymers occur within a respectfully natural environment, or without human intervention.


Biomolecules

Biomolecule, Biomolecular chemistry is a major category within organic chemistry which is frequently studied by biochemists. Many complex multi-functional group molecules are important in living organisms. Some are long-chain biopolymers, and these include peptides, DNA, RNA and the polysaccharides such as starches in animals and celluloses in plants. The other main classes are amino acids (monomer building blocks of peptides and proteins), carbohydrates (which includes the polysaccharides), the nucleic acids (which include DNA and RNA as polymers), and the lipids. Besides, animal biochemistry contains many small molecule intermediates which assist in energy production through the Krebs cycle, and produces isoprene, the most common hydrocarbon in animals. Isoprenes in animals form the important steroid structural (
cholesterol Cholesterol is any of a class of certain organic compound, organic molecules. A cholesterol is a sterol (or chemical modification, modified steroid), a type of lipid. Cholesterol is biosynthesis, biosynthesized by all animal Cell (biology)#Euk ...

cholesterol
) and steroid hormone compounds; and in plants form terpenes, terpenoids, some alkaloids, and a class of hydrocarbons called biopolymer polyisoprenoids present in the latex of various species of plants, which is the basis for making rubber. See also: peptide synthesis, oligonucleotide synthesis and carbohydrate synthesis.


Small molecules

In pharmacology, an important group of organic compounds is small molecules, also referred to as 'small organic compounds'. In this context, a small molecule is a small organic compound that is biologically active but is not a
polymer A polymer (; Greek ''poly- Poly, from the Greek :wikt:πολύς, πολύς meaning "many" or "much", may refer to: Businesses * China Poly Group Corporation, a Chinese business group, and its subsidiaries: ** Poly Property, a Hong Kong inc ...

polymer
. In practice, small molecules have a molar mass less than approximately 1000 g/mol.


Fullerenes

Fullerenes and carbon nanotubes, carbon compounds with spheroidal and tubular structures, have stimulated much research into the related field of
materials science The interdisciplinary Interdisciplinarity or interdisciplinary studies involves the combination of two or more academic discipline An academic discipline or academic field is a subdivision of knowledge that is Education, taught and resea ...
. The first fullerene was discovered in 1985 by Sir Harold W. Kroto of the United Kingdom and by Richard E. Smalley and Robert F. Curl, Jr., of the United States. Using a laser to vaporize graphite rods in an atmosphere of helium gas, these chemists and their assistants obtained cagelike molecules composed of 60 carbon atoms (C60) joined together by single and double bonds to form a hollow sphere with 12 pentagonal and 20 hexagonal faces—a design that resembles a football, or soccer ball. In 1996 the trio was awarded the Nobel Prize for their pioneering efforts. The C60 molecule was named buckminsterfullerene (or, more simply, the buckyball) after the American architect R. Buckminster Fuller, whose geodesic dome is constructed on the same structural principles.


Others

Organic compounds containing bonds of carbon to nitrogen, oxygen and the halogens are not normally grouped separately. Others are sometimes put into major groups within organic chemistry and discussed under titles such as organosulfur chemistry,
organometallic chemistry Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkaline, alkaline earth, and transition metals, and s ...
, organophosphorus chemistry and Organosilicon, organosilicon chemistry.


Organic reactions

Organic reactions are chemical reactions involving
organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
s. Many of these reactions are associated with functional groups. The general theory of these reactions involves careful analysis of such properties as the electron affinity of key atoms, bond strengths and steric hindrance. These factors can determine the relative stability of short-lived reactive intermediates, which usually directly determine the path of the reaction. The basic reaction types are: Addition reaction, addition reactions, Elimination reaction, elimination reactions, Substitution reaction, substitution reactions, Pericyclic reaction, pericyclic reactions, rearrangement reactions and Redox, redox reactions. An example of a common reaction is a substitution reaction written as: :Nu + C-X → C-Nu + X where X is some functional group and Nu is a nucleophile. The number of possible organic reactions is infinite. However, certain general patterns are observed that can be used to describe many common or useful reactions. Each reaction has a stepwise reaction mechanism that explains how it happens in sequence—although the detailed description of steps is not always clear from a list of reactants alone. The stepwise course of any given reaction mechanism can be represented using arrow pushing techniques in which curved arrows are used to track the movement of electrons as starting materials transition through intermediates to final products.


Organic synthesis

Synthetic organic chemistry is an applied science as it borders engineering, the "design, analysis, and/or construction of works for practical purposes". Organic synthesis of a novel compound is a problem-solving task, where a synthesis is designed for a target molecule by selecting optimal reactions from optimal starting materials. Complex compounds can have tens of reaction steps that sequentially build the desired molecule. The synthesis proceeds by utilizing the reactivity of the functional groups in the molecule. For example, a carbonyl compound can be used as a nucleophile by converting it into an enolate, or as an electrophile; the combination of the two is called the aldol reaction. Designing practically useful syntheses always requires conducting the actual synthesis in the laboratory. The scientific practice of creating novel synthetic routes for complex molecules is called total synthesis. Strategies to design a synthesis include retrosynthesis, popularized by E.J. Corey, which starts with the target molecule and splices it to pieces according to known reactions. The pieces, or the proposed precursors, receive the same treatment, until available and ideally inexpensive starting materials are reached. Then, the retrosynthesis is written in the opposite direction to give the synthesis. A "synthetic tree" can be constructed because each compound and also each precursor has multiple syntheses.


See also

* List of important publications in chemistry#Organic chemistry, Important publications in organic chemistry * List of organic reactions * Molecular modelling


References


External links


MIT.edu
OpenCourseWare: Organic Chemistry I
HaverFord.edu
Organic Chemistry Lectures, Videos and Text
Organic-Chemistry.org
Organic Chemistry Portal – Recent Abstracts and (Name)Reactions
Orgsyn.org
Organic Chemistry synthesis journal
Clutchprep.com
Organic Chemistry Video Lectures and Practice Problems
Khanacademy.org
Khan Academy - Organic Chemistry {{DEFAULTSORT:Organic Chemistry Organic chemistry, Chemistry Organic compounds, Chemistry