1917:. 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 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
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2283:, 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
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2318:, 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.
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reader, the hashed bonds indicate the atoms are oriented away from the reader, and the solid (plain) bonds indicate the bonds are in the plane of the screen/paper. The middle structure shows the four carbon atoms. The 4th structure is a representation just showing the atoms and bonds without 3-dimensions. The right-most structure is a condensed structure representation of butane.
1095:, 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.
1854:. Biologists usually classify the above-mentioned biomolecules into four main groups, i.e., proteins, lipids, carbohydrates, and nucleic acids. Petroleum and its derivatives are considered organic molecules, which is consistent with the fact that this oil comes from the fossilization of living beings, i.e., biomolecules. See also:
732:. 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
1396:. 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.
764:. 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.
2167:
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
1265:
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
883:
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
1329:
This diagram shows 5 distinct structural representations of the organic compound butane. The left-most structure is a bond-line drawing where the hydrogen atoms are removed. The 2nd structure has the hydrogens added depicted-the dark wedged bonds indicate the hydrogen atoms are coming toward the
181:. 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).
1339:
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
1138:
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
1383:
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.
1063:
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:
1129:
The physical properties of organic compounds typically of interest include both quantitative and qualitative features. Quantitative information includes a melting point, boiling point, solubility, and index of refraction. Qualitative properties include odor, consistency, and color.
1643:
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
1266:
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.
1269:
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
1384:
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
1003:
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
1562:) 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
867:. 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-
1929:
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
1686:
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
1546:
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
2775:
Torker, Sebastian; MĂĽller, Andre; Sigrist, Raphael; Chen, Peter (2010). "Tuning the Steric
Properties of a Metathesis Catalyst for Copolymerization of Norbornene and Cyclooctene toward Complete Alternation".
716:(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
1256:
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
1624:
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
1317:
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
2303:. 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
805:
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.
2151:
1012:, 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
609:—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
1671:
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
1121:
provide relatively nonspecific structural information but remain in use for specific applications. Refractive index and density can also be important for substance identification.
836:. Ehrlich popularized the concepts of "magic bullet" drugs and of systematically improving drug therapies. His laboratory made decisive contributions to developing antiserum for
1105:
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.
1502:=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.
1139:
compounds. The melting and boiling points correlate with the polarity of the molecules and their molecular weight. Some organic compounds, especially symmetrical ones,
1721:
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
926:
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
875:, 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
669:
Organic chemistry is typically taught at the college or university level. It is considered a very challenging course, but has also been made accessible to students.
1668:
heterocycles. The heteroatom of heterocyclic molecules is generally oxygen, sulfur, or nitrogen, with the latter being particularly common in biochemical systems.
1147:, the odiferous constituent of modern mothballs. Organic compounds are usually not very stable at temperatures above 300 °C, although some exceptions exist.
3163:
2333:
2037:. Many of these reactions are associated with functional groups. The general theory of these reactions involves careful analysis of such properties as the
1921:(or, more simply, the buckyball) after the American architect R. Buckminster Fuller, whose geodesic dome is constructed on the same structural principles.
2662:
2175:
techniques in which curved arrows are used to track the movement of electrons as starting materials transition through intermediates to final products.
1890:, 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
999:
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
1075:. The principal constituent atoms of organic chemistry – hydrogen and carbon – exist naturally with NMR-responsive isotopes, respectively H and C.
3211:
3029:
1293:
With the increased use of computing, other naming methods have evolved that are intended to be interpreted by machines. Two popular formats are
1474:
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 p
991:
The majority of chemical compounds occurring in biological organisms are carbon compounds, so the association between organic chemistry and
884:
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
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double bonds. This means that every carbon atom in the ring is sp2 hybridized, allowing for added stability. The most important example is
437:
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therefore basic nature of group) points towards it and decreases in strength with increasing distance. Dipole distance (measured in
2609:
1071:
is the most commonly used technique, often permitting the complete assignment of atom connectivity and even stereochemistry using
3295:
3143:
1574:). Saturated cyclic compounds contain single bonds only, whereas aromatic rings have an alternating (or conjugated) double bond.
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A crucial breakthrough for organic chemistry was the concept of chemical structure, developed independently in 1858 by both
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alkenes (olefins): aliphatic hydrocarbons that contain one or more double bonds, i.e. di-olefins (dienes) or poly-olefins.
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1818:. Besides, animal biochemistry contains many small molecule intermediates which assist in energy production through the
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1987:
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2013:
1081:: A destructive method used to determine the elemental composition of a molecule. See also mass spectrometry, below.
119:
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1995:
1913:, carbon compounds with spheroidal and tubular structures, have stimulated much research into the related field of
790:. His discovery, made widely known through its financial success, greatly increased interest in organic chemistry.
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86:
2680:"The contributions of Paul Ehrlich to pharmacology: A tribute on the occasion of the centenary of his Nobel Prize"
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towards the functional group have an intermolecular and intramolecular effect on the surrounding environment and
17:
2641:. New Delhi: Medtech (Scientific International, reprint of revised 4th edition, Macmillan, 1998). pp. 3–4.
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on another molecule (intermolecular) or within the same molecule (intramolecular). Any group with a net acidic p
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1991:
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1460:. More basic/nucleophilic functional groups desire to attack an electrophilic functional group with a lower p
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is so close that biochemistry might be regarded as in essence a branch of organic chemistry. Although the
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1261:(International Union of Pure and Applied Chemistry). Systematic nomenclature starts with the name for a
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1774:. Many complex multi-functional group molecules are important in living organisms. Some are long-chain
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values and bond strengths (single, double, triple) leading to increased electrophilicity with lower p
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1976:
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is one of the best-known aromatic compounds as it is one of the simplest and most stable aromatics.
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are of interest depending on applications, e.g. thermo-mechanical and electro-mechanical such as
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worked on the organization of organic chemistry, being considered one of its principal founders.
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1417:, when measured, increases in strength. A dipole directed towards the functional group (higher p
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1226:) properties. For historical reasons, such properties are mainly the subjects of the areas of
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1748:. Biopolymers occur within a respectfully natural environment, or without human intervention.
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were shown to be large organic molecules, and petroleum was shown to be of biological origin.
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enabling a broad range of industrial and commercial products including, among (many) others:
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spurred the development of organic chemistry. Converting individual petroleum compounds into
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obtained from living organisms were endowed with a vital force that distinguished them from
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and constitute the majority of known chemicals. The bonding patterns of carbon, with its
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543:) as well as compounds based on carbon, but also containing other elements, especially
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in water than inorganic solvents. Exceptions include organic compounds that contain
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2465:"A Snapshot of Organic Chemistry Instruction and Curriculum over the Past 100 Years"
1744:. Synthetic polymers are artificially manufactured, and are commonly referred to as
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The multiple-step synthesis of complex organic compounds is called total synthesis.
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Shriner, R.L.; Hermann, C.K.F.; Morrill, T.C.; Curtin, D.Y. and Fuson, R.C. (1997)
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1826:, the most common hydrocarbon in animals. Isoprenes in animals form the important
1190:. Solubility varies widely with the organic solute and with the organic solvent.
4002:
3958:
3953:
3847:
3823:
3657:
3620:
3473:
3463:
3346:
3173:
2892:
Evieux, E. A. (1954-06-01). "The Geneva
Congress on Organic Nomenclature, 1892".
2304:
2276:
1910:
1692:
1661:
1626:
1542:
alkynes (acetylenes): aliphatic hydrocarbons which have one or more triple bonds.
1413:) of the molecular addition/functional group increases, there is a corresponding
1227:
1199:
1179:
1098:
1045:
1005:
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In addition, contemporary research focuses on organic chemistry involving other
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1846:, and a class of hydrocarbons called biopolymer polyisoprenoids present in the
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industry began in the last decade of the 19th century when the German company,
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265:
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2728:"Paul Ehrlich, the Rockefeller Institute, and the first targeted chemotherapy"
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The stepwise course of any given reaction mechanism can be represented using
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Blackie, Margaret A.L.; Arnott, Gareth; Kaschula, Catherine H. (2023-09-12).
2172:
2042:
1943:
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is a major category within organic chemistry which is frequently studied by
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1290:-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo- quinoline-9-carboxamide.
1156:
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931:
919:
532:
3189:
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Streitwieser, Andrew; Heathcock, Clayton H.; Kosower, Edward M. (2017).
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How to Use
Biological Abstracts, Chemical Abstracts and Index Chemicus
2789:
2695:
2362:
2360:
2358:
1495:
values are most likely to be attacked, followed by carboxylic acids (p
1032:
techniques are especially important for this application, and include
605:
of four—formal single, double, and triple bonds, plus structures with
4054:
3356:
3221:
1906:
1839:
1799:
1672:
1665:
1559:
1164:
1028:, a variety of techniques have also been developed to assess purity;
985:
981:
957:
915:
872:
591:
525:
458:
195:
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2188:
2049:. These factors can determine the relative stability of short-lived
1965:
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35:
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1649:
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occurs. Otherwise, organic compounds tend to dissolve in organic
4096:
3060:, Organic Chemistry Portal – Recent Abstracts and (Name)Reactions
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817:
816:, first manufactured acetylsalicylic acid—more commonly known as
779:
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517:
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356:
2942:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
2400:
Morrison, Robert T.; Boyd, Robert N. and Boyd, Robert K. (1992)
1851:
1795:
1683:
1516:
The aliphatic hydrocarbons are subdivided into three groups of
1414:
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900:
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729:
552:
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478:
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260:
1629:) is conferred by the presence of 4n conjugated pi electrons.
888:. In 2002, 17,000 tons of synthetic indigo were produced from
2934:
2073:
2053:, which usually directly determine the path of the reaction.
1847:
1815:
1653:
1389:
1309:
Organic molecules are described more commonly by drawings or
1298:
1258:
1175:
828:, (Salvarsan), as the first effective medicinal treatment of
813:
745:
634:
572:
531:
The range of chemicals studied in organic chemistry includes
290:
2822:
2636:
2582:
Kiefer, D. M. (1993). "Organic
Chemicals' Mauve Beginning".
1886:
In pharmacology, an important group of organic compounds is
1850:
of various species of plants, which is the basis for making
1143:. A well-known example of a sublimable organic compound is
847:
An example of an organometallic molecule, a catalyst called
4071:
2802:
Steingruber, Elmar (2004) "Indigo and Indigo
Colorants" in
2424:"Engaging Organic Chemistry Students in Knowledge Building"
1874:
741:
721:
610:
513:
481:
922:-related compounds have opened ways to synthesize complex
4081:
3063:
2825:
Classics in Total
Synthesis: Targets, Strategies, Methods
1787:
1783:
1675:, vitamins, steroids, and nucleic acids (e.g. DNA, RNA).
1486:
1248:
984:, and various property-modifying petroleum additives and
783:
725:
280:
3072:, Organic Chemistry Video Lectures and Practice Problems
2536:
Henry
Marshall Leicester; Herbert S. Klickstein (1951).
1528:
alkanes (paraffins): aliphatic hydrocarbons without any
910:
of complex natural compounds increased in complexity to
824:
and his laboratory group began developing arsenic-based
27:
Subdiscipline of chemistry, focusing on carbon compounds
2774:
2550:
1433:
1347:
1313:, combinations of drawings and chemical symbols. The
1252:
Various names and depictions for one organic compound.
2421:
2089:
863:(=CHPh), where the ball-and-stick model is based on
465:
study of the structure, properties, and reactions of
2261:(Tamiflu). This synthesis has 11 distinct reactions.
1834:) and steroid hormone compounds; and in plants form
1806:(monomer building blocks of peptides and proteins),
1392:, and usually can be converted to the corresponding
1678:Rings can fuse with other rings on an edge to give
879:, contains a metal-carbon double bond to ruthenium.
60:. Unsourced material may be challenged and removed.
2873:The Systematic Identification of Organic Compounds
2145:
968:of compounds by various chemical processes led to
3115:
2503:
2146:{\displaystyle {\ce {Nu- + C-X -> C-Nu + X-}}}
1814:(which include DNA and RNA as polymers), and the
1133:
4170:
1453:and increased nucleophile strength with higher p
952:marked a major achievement in organic chemistry.
832:, and thereby initiated the medical practice of
2677:
2544:
2366:Clayden, J.; Greeves, N. and Warren, S. (2012)
2945:(6th ed.), New York: Wiley-Interscience,
2804:Ullmann's Encyclopedia of Industrial Chemistry
173:Three representations of an organic compound,
3205:
3101:
3054:, Organic Chemistry Lectures, Videos and Text
2581:
2168:always clear from a list of reactants alone.
1069:Nuclear magnetic resonance (NMR) spectroscopy
1040:. Traditional methods of separation include
431:
1725:, while the chains, or networks, are called
1656:are examples of aromatic heterocycles while
1439:Different functional groups have different p
571:is the study of compounds containing carbon–
3028:: CS1 maint: numeric names: authors list (
2671:
2334:Important publications in organic chemistry
2299:; the combination of the two is called the
2217:. Unsourced material may be challenged and
1994:. Unsourced material may be challenged and
1612:, the structure of which was formulated by
1578:do not contain multiple bonds, whereas the
500:to understand their behavior. The study of
3212:
3198:
3108:
3094:
3002:
2610:"August Kekulé and Archibald Scott Couper"
2557:Proceedings of the Royal Society of London
2551:Royal Society of London (1 January 1875).
1810:(which includes the polysaccharides), the
1340:compound. This led to the creation of the
1109:Traditional spectroscopic methods such as
641:. The study of organic chemistry overlaps
438:
424:
3219:
2703:
2602:
2480:
2439:
2310:Strategies to design a synthesis include
2237:Learn how and when to remove this message
2014:Learn how and when to remove this message
1632:
1193:
685:Timeline of biology and organic chemistry
594:, nickel, cobalt, titanium and chromium.
120:Learn how and when to remove this message
2540:. Harvard University Press. p. 309.
2248:
1873:
1755:
1702:
1589:
1356:
1324:
1247:
939:
842:
689:
621:, and products made from them including
597:Organic compounds form the basis of all
2851:Allan, Barbara. Livesey, Brian (1994).
2823:Nicolaou, K.C.; Sorensen, E.J. (1996).
2796:
2076:. An example of a common reaction is a
1244:IUPAC nomenclature of organic chemistry
1024:Since organic compounds often exist as
895:In the early part of the 20th century,
524:in the laboratory and via theoretical (
14:
4171:
2891:
2553:"Obituary Notices of Fellows Deceased"
1894:. In practice, small molecules have a
1802:in plants. The other main classes are
1505:
1304:
840:and standardizing therapeutic serums.
664:
484:. Study of structure determines their
3193:
3089:
3066:, Organic Chemistry synthesis journal
3048:, OpenCourseWare: Organic Chemistry I
2989:"industrial polymers, chemistry of."
2538:A Source Book in Chemistry, 1400-1900
2462:
2370:. Oxford University Press. pp. 1–15.
1763:, a complex organic biological toxin.
1585:
1155:Neutral organic compounds tend to be
4127:
2215:adding citations to reliable sources
2182:
2178:
1992:adding citations to reliable sources
1959:
1949:
1898:less than approximately 1000 g/mol.
1485:components with the lowest measured
1352:
851:. Its formula is often given as RuCl
782:, accidentally produced the organic
58:adding citations to reliable sources
29:
4151:
2742:
1348:Classification of organic compounds
1019:
24:
2630:
2497:
2275:Synthetic organic chemistry is an
1869:
1736:Two main groups of polymers exist
1729:. The source compound is called a
1365:acids contains a carboxyl (-COOH)
1198:Various specialized properties of
801:. Both researchers suggested that
520:, and study of individual organic
477:in its various forms that contain
25:
4200:
3039:
2661:Roberts, Laura (7 December 2010)
2639:Introduction to Organic Chemistry
1536:, i.e. just C-C, C-H single bonds
4150:
4138:
4126:
4115:
4114:
2187:
1964:
1711:, it is an example of a polymer.
405:
404:
391:
202:
160:
148:
136:
34:
2996:
2983:
2958:
2928:
2885:
2865:
2845:
2816:
2768:
2720:
2655:
2463:Holme, Thomas A. (2023-06-13).
1751:
1707:This swimming board is made of
1237:
1214:, electrical conductivity (see
683:For a chronological guide, see
488:. Study of properties includes
45:needs additional citations for
2966:"The pKa Table Is Your Friend"
2575:
2529:
2456:
2415:
2404:, 6th ed., Benjamin Cummings.
2394:
2381:
2115:
2072:, rearrangement reactions and
2056:The basic reaction types are:
1134:Melting and boiling properties
1101:can be useful for determining
778:, while trying to manufacture
752:starting materials (the salts
744:(carbamide), a constituent of
712:. According to the concept of
13:
1:
3479:Interface and colloid science
3233:Glossary of chemical formulae
2894:Journal of Chemical Education
2812:10.1002/14356007.a14_149.pub2
2469:Journal of Chemical Education
2428:Journal of Chemical Education
2349:
1901:
1691:and are important in several
1222:), and electro-optical (e.g.
1150:
1124:
760:), in what is now called the
155:Ball-and-stick representation
2328:Outline of organic chemistry
1520:according to their state of
1373:, shown here, is an example.
1334:
1091:of a compound and, from the
167:Space-filling representation
7:
3756:Bioorganometallic chemistry
3243:List of inorganic compounds
2482:10.1021/acs.jchemed.3c00467
2441:10.1021/acs.jchemed.2c00980
2321:
1698:
1274:is systematically named (6a
960:and the development of the
535:(compounds containing only
10:
4205:
3682:Dynamic covalent chemistry
3653:Enantioselective synthesis
3633:Physical organic chemistry
3586:Organolanthanide chemistry
2678:Bosch F; Rosich L (2008).
2325:
2287:compound can be used as a
2264:
1953:
1940:organophosphorus chemistry
1714:
1636:
1509:
1376:
1272:lysergic acid diethylamide
1241:
682:
676:
672:
4110:
4013:
3774:
3690:
3611:
3561:
3437:
3380:
3271:Electroanalytical methods
3256:
3228:
3179:List of organic compounds
3124:
2875:. John Wiley & Sons,
2754:Science History Institute
2615:Science History Institute
2596:10.1021/cen-v071n032.p022
2509:Chemistry of the Elements
2507:; Earnshaw, Alan (1997).
2387:Elschenbroich, C. (2006)
2339:List of organic reactions
2291:by converting it into an
1924:
1860:oligonucleotide synthesis
1582:and the cycloalkynes do.
1159:; that is, they are less
700:Before the 18th century,
377:List of unsolved problems
143:Line-angle representation
4026:Nobel Prize in Chemistry
3942:Supramolecular chemistry
3581:Organometallic chemistry
2970:Master Organic Chemistry
2730:. Rockefeller University
2253:A synthesis designed by
1936:organometallic chemistry
1555:in petroleum chemistry.
1073:correlation spectroscopy
704:generally believed that
643:organometallic chemistry
569:Organometallic chemistry
367:List of chemistry awards
3964:Combinatorial chemistry
3875:Food physical chemistry
3838:Environmental chemistry
3722:Bioorthogonal chemistry
3648:Retrosynthetic analysis
3469:Chemical thermodynamics
3452:Spectroelectrochemistry
3395:Computational chemistry
2991:Encyclopædia Britannica
2806:, Wiley-VCH, Weinheim.
1944:organosilicon chemistry
1616:who first proposed the
997:history of biochemistry
795:Friedrich August Kekulé
4036:of element discoveries
3882:Agricultural chemistry
3870:Carbohydrate chemistry
3761:Bioinorganic chemistry
3626:Alkane stereochemistry
3571:Coordination chemistry
3400:Mathematical chemistry
3266:Instrumental chemistry
3003:Meinschein (2), W. G.
2262:
2147:
2066:substitution reactions
2051:reactive intermediates
1932:organosulfur chemistry
1883:
1864:carbohydrate synthesis
1768:Biomolecular chemistry
1764:
1712:
1664:are the corresponding
1633:Heterocyclic compounds
1598:
1374:
1331:
1253:
1220:organic semiconductors
1194:Solid state properties
1167:groups as well as low
1093:fragmentation patterns
962:petrochemical industry
953:
880:
799:Archibald Scott Couper
697:
175:5α-Dihydroprogesterone
4031:Timeline of chemistry
3928:Post-mortem chemistry
3913:Clandestine chemistry
3843:Atmospheric chemistry
3766:Biophysical chemistry
3598:Solid-state chemistry
3548:Equilibrium chemistry
3457:Photoelectrochemistry
3058:Organic-Chemistry.org
3005:"Origin of Petroleum"
2513:Butterworth-Heinemann
2505:Greenwood, Norman N.
2252:
2148:
2078:substitution reaction
2062:elimination reactions
1877:
1759:
1706:
1639:Heterocyclic compound
1604:hydrocarbons contain
1593:
1360:
1328:
1251:
1111:infrared spectroscopy
943:
865:X-ray crystallography
846:
693:
607:delocalized electrons
586:, but especially the
4021:History of chemistry
3976:Chemical engineering
3751:Bioorganic chemistry
3501:Structural chemistry
3238:List of biomolecules
2211:improve this section
2087:
2070:pericyclic reactions
1988:improve this section
1919:buckminsterfullerene
1878:Molecular models of
1778:, and these include
1680:polycyclic compounds
1145:para-dichlorobenzene
1010:Biological Abstracts
871:bond, tricyclohexyl
776:William Henry Perkin
679:History of chemistry
496:, and evaluation of
398:Chemistry portal
319:Analytical chemistry
296:Chemical equilibrium
54:improve this article
4044:The central science
3998:Ceramic engineering
3923:Forensic toxicology
3896:Chemistry education
3794:Radiation chemistry
3776:Interdisciplinarity
3729:Medicinal chemistry
3667:Fullerene chemistry
3543:Microwave chemistry
3412:Molecular mechanics
3407:Molecular modelling
3082:- Organic Chemistry
2935:Smith, Michael B.;
2906:1954JChEd..31..326E
2344:Molecular modelling
1746:industrial polymers
1506:Aliphatic compounds
1311:structural formulas
1305:Structural drawings
1216:conductive polymers
1119:UV/VIS spectroscopy
1054:magnetic separation
720:started a study of
710:inorganic compounds
665:Educational aspects
651:medicinal chemistry
498:chemical reactivity
494:chemical properties
334:Inorganic chemistry
190:Part of a series on
69:"Organic chemistry"
4087:Chemical substance
3949:Chemical synthesis
3918:Forensic chemistry
3799:Actinide chemistry
3741:Clinical chemistry
3422:Molecular geometry
3417:Molecular dynamics
3372:Elemental analysis
3325:Separation process
2663:History of Aspirin
2391:3rd Ed., Wiley-VCH
2267:Chemical synthesis
2263:
2143:
2058:addition reactions
2031:chemical reactions
1884:
1765:
1738:synthetic polymers
1713:
1599:
1586:Aromatic compounds
1512:Aliphatic compound
1375:
1332:
1315:line-angle formula
1254:
1208:conjugated systems
1200:molecular crystals
1103:molecular geometry
1079:Elemental analysis
1058:solvent extraction
1038:gas chromatography
954:
881:
724:made from various
698:
559:(included in many
506:chemical synthesis
486:structural formula
339:Physical chemistry
286:Acid–base reaction
4189:Organic compounds
4179:Organic chemistry
4166:
4165:
4102:Quantum mechanics
4067:Chemical compound
4050:Chemical reaction
3988:Materials science
3906:General chemistry
3901:Amateur chemistry
3829:Photogeochemistry
3814:Stellar chemistry
3784:Nuclear chemistry
3705:Molecular biology
3672:Polymer chemistry
3643:Organic synthesis
3638:Organic reactions
3603:Ceramic chemistry
3593:Cluster chemistry
3523:Chemical kinetics
3511:Molecular physics
3390:Quantum chemistry
3303:Mass spectrometry
3187:
3186:
3159:Organic synthesis
3154:Organic reactions
3149:Organic compounds
3139:Functional groups
3118:organic chemistry
2952:978-0-471-72091-1
2914:10.1021/ed031p326
2861:978-0-566-07556-8
2838:978-3-527-29231-8
2790:10.1021/om100185g
2784:(12): 2735–2751.
2696:10.1159/000149583
2648:978-93-85998-89-8
2522:978-0-08-037941-8
2402:Organic Chemistry
2368:Organic Chemistry
2314:, popularized by
2271:Organic synthesis
2247:
2246:
2239:
2179:Organic synthesis
2135:
2128:
2120:
2114:
2106:
2094:
2039:electron affinity
2035:organic compounds
2027:Organic reactions
2024:
2023:
2016:
1950:Organic reactions
1915:materials science
1856:peptide synthesis
1518:homologous series
1353:Functional groups
1232:materials science
1224:non-linear optics
1085:Mass spectrometry
970:organic reactions
956:The discovery of
769:Justus von Liebig
754:potassium cyanate
659:materials science
655:polymer chemistry
588:transition metals
502:organic reactions
471:organic materials
467:organic compounds
451:Organic chemistry
448:
447:
329:Organic chemistry
276:Chemical reaction
209:Science of matter
130:
129:
122:
104:
16:(Redirected from
4196:
4154:
4153:
4142:
4130:
4129:
4118:
4117:
4062:Chemical element
3717:Chemical biology
3576:Magnetochemistry
3553:Mechanochemistry
3506:Chemical physics
3447:Electrochemistry
3352:Characterization
3214:
3207:
3200:
3191:
3190:
3134:Covalent bonding
3110:
3103:
3096:
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3086:
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2527:
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2511:(2nd ed.).
2501:
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2475:(6): 2093–2095.
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2191:
2183:
2158:functional group
2156:where X is some
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2125:
2118:
2112:
2111:
2104:
2100:
2099:
2092:
2047:steric hindrance
2019:
2012:
2008:
2005:
1999:
1968:
1960:
1956:Organic reaction
1911:carbon nanotubes
1693:natural products
1558:Both saturated (
1430:steric hindrance
1379:Functional group
1367:functional group
1263:parent structure
1212:piezoelectricity
1204:organic polymers
1184:hydrogen bonding
1180:carboxylic acids
1169:molecular weight
1115:optical rotation
1089:molecular weight
1020:Characterization
978:synthetic rubber
886:Adolf von Baeyer
849:Grubbs' catalyst
762:Wöhler synthesis
758:ammonium sulfate
734:Friedrich Wöhler
695:Friedrich Wöhler
649:, but also with
510:natural products
440:
433:
426:
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408:
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372:List of journals
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4003:Polymer science
3959:Click chemistry
3954:Green chemistry
3848:Ocean chemistry
3824:Biogeochemistry
3770:
3686:
3658:Total synthesis
3621:Stereochemistry
3607:
3557:
3474:Surface science
3464:Thermochemistry
3433:
3376:
3347:Crystallography
3252:
3224:
3218:
3188:
3183:
3174:Stereochemistry
3120:
3114:
3076:Khanacademy.org
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2778:Organometallics
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2584:Chem. Eng. News
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2389:Organometallics
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2305:total synthesis
2277:applied science
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2074:redox reactions
2020:
2009:
2003:
2000:
1985:
1969:
1958:
1952:
1927:
1904:
1888:small molecules
1872:
1870:Small molecules
1822:, and produces
1798:in animals and
1792:polysaccharides
1754:
1719:
1701:
1662:tetrahydrofuran
1641:
1635:
1627:antiaromaticity
1588:
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1388:, usually form
1381:
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1337:
1307:
1246:
1240:
1228:polymer science
1196:
1153:
1136:
1127:
1099:Crystallography
1046:crystallization
1022:
1006:BIOSIS Previews
951:
946:total synthesis
935:
918:. For example,
908:Total synthesis
862:
858:
854:
808:The era of the
718:Michel Chevreul
688:
681:
675:
667:
611:pharmaceuticals
580:organometallics
444:
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18:Organic chemist
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3865:Food chemistry
3862:
3860:Carbochemistry
3857:
3855:Clay chemistry
3852:
3851:
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3810:Astrochemistry
3806:Cosmochemistry
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3789:Radiochemistry
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3746:Neurochemistry
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3677:Petrochemistry
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3538:Spin chemistry
3535:
3533:Photochemistry
3530:
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3518:Femtochemistry
3515:
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3330:Chromatography
3327:
3322:
3321:
3320:
3315:
3310:
3300:
3299:
3298:
3293:
3288:
3283:
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3262:
3260:
3254:
3253:
3251:
3250:
3248:Periodic table
3245:
3240:
3235:
3229:
3226:
3225:
3217:
3216:
3209:
3202:
3194:
3185:
3184:
3182:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3125:
3122:
3121:
3113:
3112:
3105:
3098:
3090:
3084:
3083:
3073:
3070:Clutchprep.com
3067:
3061:
3055:
3049:
3041:
3040:External links
3038:
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2957:
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2927:
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2864:
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2815:
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2767:
2750:"Paul Ehrlich"
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2563:: xxvii–xxxvii
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2410:978-0136436690
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2380:
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2326:Main article:
2323:
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2312:retrosynthesis
2301:aldol reaction
2279:as it borders
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2154:
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2110:
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2098:
2043:bond strengths
2041:of key atoms,
2022:
2021:
1972:
1970:
1963:
1954:Main article:
1951:
1948:
1926:
1923:
1903:
1900:
1871:
1868:
1753:
1750:
1723:polymerization
1715:Main article:
1700:
1697:
1637:Main article:
1634:
1631:
1618:delocalization
1587:
1584:
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1543:
1540:
1537:
1510:Main article:
1507:
1504:
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1377:Main article:
1361:The family of
1354:
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1333:
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1303:
1242:Main article:
1239:
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1195:
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1149:
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1126:
1123:
1107:
1106:
1096:
1087:indicates the
1082:
1076:
1030:chromatography
1021:
1018:
949:
933:
924:human hormones
890:petrochemicals
860:
856:
852:
810:pharmaceutical
788:Perkin's mauve
767:After Wöhler,
677:Main article:
674:
671:
666:
663:
615:petrochemicals
590:zinc, copper,
582:including the
461:involving the
446:
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255:Key components
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3999:
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3994:
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3990:
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3981:Stoichiometry
3979:
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3937:Nanochemistry
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3662:Semisynthesis
3659:
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3496:Sonochemistry
3494:
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3491:Cryochemistry
3489:
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3484:Micromeritics
3482:
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3362:Wet chemistry
3360:
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3062:
3059:
3056:
3053:
3052:HaverFord.edu
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2668:
2667:The Telegraph
2664:
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2590:(32): 22–23.
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2227:November 2021
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2201:
2196:This section
2194:
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2173:arrow pushing
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2018:
2015:
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2004:November 2021
1997:
1993:
1989:
1983:
1982:
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1973:This section
1971:
1967:
1962:
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1812:nucleic acids
1809:
1808:carbohydrates
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1553:cetane number
1550:
1549:octane number
1541:
1538:
1535:
1531:
1527:
1526:
1525:
1523:
1519:
1513:
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1501:
1494:
1493:
1484:
1483:acyl chloride
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983:
979:
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929:
928:lysergic acid
925:
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893:
891:
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831:
827:
823:
819:
815:
811:
806:
804:
800:
796:
791:
789:
786:now known as
785:
781:
777:
772:
770:
765:
763:
759:
755:
751:
747:
743:
739:
736:produced the
735:
731:
727:
723:
719:
715:
711:
707:
703:
696:
692:
686:
680:
670:
662:
660:
656:
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648:
644:
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632:
628:
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619:agrichemicals
616:
612:
608:
604:
600:
595:
593:
589:
585:
581:
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574:
570:
566:
562:
558:
554:
550:
546:
542:
538:
534:
529:
527:
523:
519:
515:
511:
507:
504:includes the
503:
499:
495:
491:
487:
483:
480:
476:
472:
468:
464:
460:
456:
455:subdiscipline
452:
441:
436:
434:
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427:
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421:
419:
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332:
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124:
121:
113:
102:
99:
95:
92:
88:
85:
81:
78:
74:
71: –
70:
66:
65:Find sources:
59:
55:
49:
48:
43:This article
41:
37:
32:
31:
19:
4155:
4143:
4131:
4119:
3969:Biosynthesis
3819:Geochemistry
3734:Pharmacology
3710:Cell biology
3700:Biochemistry
3612:
3528:Spectroscopy
3427:VSEPR theory
3276:Spectroscopy
3220:Branches of
3169:Spectroscopy
3164:Publications
3144:Nomenclature
3117:
3116:Concepts in
3080:Khan Academy
3012:. Retrieved
3008:
2998:
2985:
2974:. Retrieved
2972:. 2010-06-18
2969:
2960:
2941:
2937:March, Jerry
2930:
2897:
2893:
2887:
2872:
2867:
2852:
2847:
2824:
2818:
2803:
2798:
2781:
2777:
2770:
2758:. Retrieved
2753:
2744:
2732:. Retrieved
2722:
2690:(3): 171–9.
2687:
2684:Pharmacology
2683:
2673:
2666:
2657:
2638:
2632:
2620:. Retrieved
2613:
2604:
2587:
2583:
2577:
2565:. Retrieved
2560:
2556:
2546:
2537:
2531:
2508:
2499:
2472:
2468:
2458:
2431:
2427:
2417:
2401:
2396:
2388:
2383:
2367:
2309:
2297:electrophile
2274:
2233:
2224:
2209:Please help
2197:
2170:
2166:
2160:and Nu is a
2155:
2080:written as:
2055:
2025:
2010:
2001:
1986:Please help
1974:
1928:
1905:
1885:
1830:structural (
1766:
1752:Biomolecules
1735:
1720:
1677:
1670:
1642:
1600:
1580:cycloalkenes
1576:Cycloalkanes
1564:cyclopropane
1557:
1545:
1534:triple bonds
1515:
1496:
1488:
1475:
1468:
1461:
1454:
1447:
1440:
1438:
1418:
1402:
1398:
1382:
1342:Geneva rules
1338:
1308:
1292:
1287:
1283:
1279:
1275:
1268:
1255:
1238:Nomenclature
1197:
1154:
1137:
1128:
1108:
1062:
1042:distillation
1023:
1001:biochemistry
1000:
993:biochemistry
990:
965:
955:
948:of vitamin B
905:
894:
882:
834:chemotherapy
826:arsphenamine
822:Paul Ehrlich
807:
792:
773:
766:
749:
737:
699:
668:
647:biochemistry
599:earthly life
596:
577:
561:biochemicals
533:hydrocarbons
530:
450:
449:
328:
324:Biochemistry
301:Chemical law
208:
177:(5α-DHP), a
116:
107:
97:
90:
83:
76:
64:
52:Please help
47:verification
44:
4157:WikiProject
3382:Theoretical
3367:Calorimetry
3129:Aromaticity
2756:. June 2016
2618:. June 2016
2295:, or as an
2289:nucleophile
2281:engineering
2259:oseltamivir
2162:nucleophile
1832:cholesterol
1820:Krebs cycle
1804:amino acids
1776:biopolymers
1772:biochemists
1742:biopolymers
1709:polystyrene
1646:heterocycle
1386:hydrophilic
1371:Acetic acid
1320:tetravalent
1157:hydrophobic
1050:evaporation
920:cholesterol
803:tetravalent
584:lanthanides
4173:Categories
3993:Metallurgy
3692:Biological
3258:Analytical
3064:Orgsyn.org
2976:2021-03-16
2900:(6): 326.
2567:5 November
2350:References
2316:E.J. Corey
2265:See also:
2255:E.J. Corey
2033:involving
1907:Fullerenes
1902:Fullerenes
1896:molar mass
1840:terpenoids
1800:celluloses
1761:Maitotoxin
1658:piperidine
1606:conjugated
1522:saturation
1363:carboxylic
1151:Solubility
1125:Properties
980:, organic
877:alkylidene
838:diphtheria
820:. By 1910
639:explosives
623:lubricants
563:) and the
557:phosphorus
463:scientific
80:newspapers
4184:Chemistry
4055:Catalysis
3563:Inorganic
3357:Titration
3222:chemistry
2922:0021-9584
2855:. Gower.
2491:0021-9584
2450:0021-9584
2198:does not
2138:−
2123:−
2116:⟶
2109:−
2097:−
1975:does not
1844:alkaloids
1673:alkaloids
1666:alicyclic
1622:resonance
1560:alicyclic
1426:Angstroms
1344:in 1892.
1165:ionizable
986:catalysts
982:adhesives
958:petroleum
932:vitamin B
916:terpineol
873:phosphine
774:In 1856,
750:inorganic
740:chemical
706:compounds
592:palladium
528:) study.
526:in silico
522:molecules
459:chemistry
196:Chemistry
4121:Category
4077:Molecule
4014:See also
3439:Physical
3024:cite web
3009:AAPG.org
2939:(2007),
2760:20 March
2714:18679046
2622:20 March
2322:See also
2285:carbonyl
1880:caffeine
1836:terpenes
1824:isoprene
1796:starches
1794:such as
1790:and the
1780:peptides
1727:polymers
1699:Polymers
1650:Pyridine
1602:Aromatic
1411:basicity
1322:carbon.
1188:solvents
1172:alcohols
1026:mixtures
1014:database
974:plastics
897:polymers
830:syphilis
714:vitalism
702:chemists
631:plastics
627:solvents
565:halogens
549:nitrogen
541:hydrogen
518:polymers
490:physical
473:, i.e.,
411:Category
351:Research
313:Branches
243:timeline
230:Glossary
4133:Commons
4097:Alchemy
3613:Organic
3046:MIT.edu
2902:Bibcode
2705:2790789
2293:enolate
2219:removed
2204:sources
1996:removed
1981:sources
1892:polymer
1842:, some
1828:steroid
1731:monomer
1717:Polymer
1610:benzene
1595:Benzene
1436:level.
1399:As the
1394:halides
1335:History
1161:soluble
1141:sublime
912:glucose
901:enzymes
818:aspirin
780:quinine
748:, from
738:organic
730:alkalis
673:History
603:valence
575:bonds.
457:within
357:Chemist
239:History
225:Outline
94:scholar
4145:Portal
3291:UV-Vis
2993:. 2006
2949:
2920:
2879:
2859:
2835:
2712:
2702:
2645:
2519:
2489:
2448:
2408:
2374:
1925:Others
1852:rubber
1816:lipids
1684:purine
1682:. The
1614:Kekulé
1530:double
1428:) and
1415:dipole
1390:esters
1295:SMILES
1182:where
1178:, and
1176:amines
1117:, and
869:ligand
657:, and
553:sulfur
545:oxygen
537:carbon
516:, and
479:carbon
475:matter
409:
261:Matter
96:
89:
82:
75:
67:
3318:MALDI
3286:Raman
3014:3 May
2829:Wiley
2734:3 Aug
1848:latex
1689:spiro
1654:furan
1409:(aka
1299:InChI
1259:IUPAC
1206:with
966:types
814:Bayer
746:urine
722:soaps
635:fuels
573:metal
514:drugs
482:atoms
453:is a
291:Redox
266:Phase
220:Index
101:JSTOR
87:books
4072:Atom
3340:HPLC
3030:link
3016:2024
2947:ISBN
2918:ISSN
2877:ISBN
2857:ISBN
2833:ISBN
2762:2018
2736:2012
2710:PMID
2643:ISBN
2624:2018
2569:2014
2517:ISBN
2487:ISSN
2446:ISSN
2406:ISBN
2372:ISBN
2269:and
2257:for
2202:any
2200:cite
2045:and
2029:are
1979:any
1977:cite
1942:and
1909:and
1862:and
1740:and
1660:and
1652:and
1566:((CH
1297:and
1230:and
1218:and
1202:and
1056:and
1036:and
1034:HPLC
1008:and
944:The
930:and
914:and
899:and
855:(PCy
797:and
756:and
742:urea
728:and
726:fats
645:and
637:and
617:and
539:and
492:and
469:and
361:list
271:Bond
73:news
4082:Ion
3313:ICP
3296:NMR
2910:doi
2808:doi
2786:doi
2700:PMC
2692:doi
2592:doi
2477:doi
2473:100
2436:doi
2432:100
2213:by
1990:by
1858:,
1788:RNA
1784:DNA
1648:.
1620:or
1551:or
1532:or
784:dye
508:of
281:Ion
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