Organic chemistry

Methane, CH4; the line-angle structural formula shows four carbon-hydrogen single bonds (σ, in black), and the typical 3D shape of tetrahedral molecules, with ~109° interior bond angles (in dashed-green).

Organic chemistry is the chemistry subdiscipline for the scientific study of structure, properties, and reactions of organic compounds and organic materials (materials that contain carbon atoms).[1] Study of structure determines their chemical composition and 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 (in silico) study.

The range of chemicals studied in organic chemistry include hydrocarbons (compounds containing only carbon and hydrogen), as well as compounds based on carbon, but also containing other elements,[1][2][3] especially oxygen, nitrogen, sulfur, phosphorus (included in many biochemicals) and the halogens.

In the modern era, the range extends further into the periodic table, with main group elements, including:

In addition, contemporary research focuses on organic chemistry involving other organometallics including the lanthanides, but especially the transition metals zinc, copper, palladium, nickel, cobalt, titanium and chromium.

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Line-angle representation
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Ball-and-stick representation
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Space-filling representation
Three representations of an organic compound, 5α-Dihydroprogesterone (5α-DHP), a steroid hormone. For molecules showing color, the carbon atoms are in black, hydrogens in gray, and oxygens in red. In the line angle representation, carbon atoms are implied at every terminus of a line and vertex of multiple lines, and hydrogen atoms are implied to fill the remaining needed valences (up to 4).

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; petrochemicals and agrichemicals, and products made from them including lubricants, solvents; plastics; fuels and explosives. The study of organic chemistry overlaps organometallic chemistry and biochemistry, but also with medicinal chemistry, polymer chemistry, and materials science.[1]

History

Before the nineteenth century, chemists generally believed that compounds obtained from living organisms were endowed with a vital force that distinguished them from inorganic compounds. According to the concept of vitalism (vital force theory), organic matter was endowed with a "vital force".[4] During the first half of the nineteenth century, some of the first systematic studies of organic compounds were reported. Around 1816 Michel Chevreul started a study of soaps made from various fats and alkalis. He separated the different 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 produced the organic chemical urea (carbamide), a constituent of urine, from inorganic starting materials (the salts potassium cyanate and ammonium sulfate), in what is now called the Wöhler synthesis. 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.[5]

In 1856 William Henry Perkin, while trying to manufacture quinine accidentally produced the organic dye now known as Perkin's mauve. His discovery, made widely known through its financial success, greatly increased interest in organic chemistry.[6]

A crucial breakthrough for organic chemistry was the concept of chemical structure, developed independently in 1858 by both Friedrich August Kekulé and Archibald Scott Couper.[7] Both researchers suggested that tetravalent 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.[8]

The era of the pharmaceutical industry began in the last decade of the 19th century when the manufacturing of acetylsalicylic acid—more commonly referred to as aspirin—in Germany was started by Bayer.[9] By 1910 Paul Ehrlich and his laboratory group began developing arsenic-based arsphenamine, (Salvarsan), as the first effective medicinal treatment of syphilis, and thereby initiated the medical practice of chemotherapy. Ehrlich popularized the concepts of "magic bullet" drugs and of systematically improving drug therapies.[10][11] His laboratory made decisive contributions to developing antiserum for diphtheria and standardizing therapeutic serums.[12]

An example of an organometallic molecule, a catalyst called Grubbs' catalyst. Its formula is often given as RuCl2(PCy3)2(=CHPh), where the ball-and-stick model is based on X-ray crystallography.[13] The single metal atom ruthenium (Ru), (in turquoise), is at the very center of the structure; two chlorines (green), are bonded to the ruthenium atom—carbon atoms are black, hydrogens gray-white, and phosphorus orange. A phosphorus-ligand bond, tricyclohexyl phosphine, PCy, is below center; (another PCy ligand appears at the top of the image where its rings are obscuring one another). The ring group projecting to the right, an alkylidene, contains a metal-carbon double bond to ruthenium.

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. In 2002, 17,000 tons of synthetic indigo were produced from petrochemicals.[14]

In the early part of the 20th century, polymers and 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 of complex natural compounds increased in complexity to glucose and terpineol. For example, cholesterol-related compounds have opened ways to synthesize complex human hormones 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 and vitamin B12.[15]

The total synthesis of vitamin B12 marked a major achievement in organic chemistry.

The discovery of petroleum and the development of the petrochemical industry spurred the development of organic chemistry. Converting individual petroleum compounds into different types of compounds by various chemical processes led to organic reactions enabling a broad range of industrial and commercial products including, among (many) others: plastics, synthetic rubber, organic adhesives, and various property-modifying petroleum additives and catalysts.

The majority of chemical compounds occurring in biological organisms are in fact carbon compounds, so the association between organic chemistry and 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 and Biological Abstracts, 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.[16]

Other Languages
Afrikaans: Organiese chemie
Alemannisch: Organische Chemie
العربية: كيمياء عضوية
aragonés: Quimica organica
অসমীয়া: জৈৱিক ৰসায়ন
azərbaycanca: Üzvi kimya
Bân-lâm-gú: Iú-ki hòa-ha̍k
башҡортса: Органик химия
беларуская: Арганічная хімія
беларуская (тарашкевіца)‎: Арганічная хімія
български: Органична химия
bosanski: Organska hemija
Cymraeg: Cemeg organig
dolnoserbski: Organiska chemija
Esperanto: Organika kemio
فارسی: شیمی آلی
Fiji Hindi: Organic chemistry
français: Chimie organique
한국어: 유기화학
hrvatski: Organska kemija
Bahasa Indonesia: Kimia organik
interlingua: Chimia organic
Basa Jawa: Kimia organik
Kiswahili: Kemia kaboni
Kreyòl ayisyen: Chimi òganik
Lëtzebuergesch: Organesch Chimie
македонски: Органска хемија
Bahasa Melayu: Kimia organik
မြန်မာဘာသာ: ဩဂဲနစ် ဓာတုဗေဒ
Nederlands: Organische chemie
日本語: 有機化学
norsk nynorsk: Organisk kjemi
Novial: Organi kemie
oʻzbekcha/ўзбекча: Organik kimyo
Plattdüütsch: Orgaansch Chemie
português: Química orgânica
русиньскый: Орґанічна хемія
Simple English: Organic chemistry
slovenčina: Organická chémia
slovenščina: Organska kemija
српски / srpski: Органска хемија
srpskohrvatski / српскохрватски: Organska hemija
Basa Sunda: Kimia organik
svenska: Organisk kemi
татарча/tatarça: Органик химия
Türkçe: Organik kimya
українська: Органічна хімія
Tiếng Việt: Hóa hữu cơ
吴语: 有机化学
粵語: 有機化學
žemaitėška: Uorganėnė chemėjė
中文: 有机化学