Portal:Organic chemistry

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The Organic chemistry Portal

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 a chemistry subdiscipline involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms. Study of structure includes many physical and chemical methods to determine the chemical composition and the chemical constitution of organic compounds and materials. Study of properties includes both physical properties and chemical properties, and uses similar methods as well as methods to evaluate chemical reactivity, with the aim to understand the behavior of the organic matter in its pure form (when possible), but also in solutions, mixtures, and fabricated forms. The study of organic reactions includes probing their scope through use in preparation of target compounds (e.g., natural products, drugs, polymers, etc.) by chemical synthesis, as well as the focused study of the reactivities of individual organic molecules, both 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 myriad compositions based always on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (these included in many organic chemicals in biology) and the radiostable elements of the halogens.

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

In addition, much modern research focuses on organic chemistry involving further organometallics, including the lanthanides, but especially the transition metals; (e.g., 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).

Finally, organic compounds form the basis of all earthly life and constitute a significant part of human endeavors in chemistry. The bonding patterns open to carbon, with its valence of four—formal single, double, and triple bonds, as well as various structures with delocalized electrons—make the array of organic compounds structurally diverse, and their range of applications enormous. They either form the basis of, or are important constituents of, many commercial products including pharmaceuticals; petrochemicals and agrichemicals, and products made from them (including lubricants, solvents, etc.); plastics; fuels and explosives; etc. As indicated, the study of organic chemistry overlaps with organometallic chemistry and biochemistry, but also with medicinal chemistry, polymer chemistry, as well as many aspects of materials science.

Selected article

The aldol reaction is an important carbon-carbon bond formation reaction in organic chemistry. In its usual form, it involves the nucleophilic addition of a ketone enolate to an aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde + alcohol), a structural unit found in many naturally occurring molecules and pharmaceuticals.

Typicalaldol2.gif

Sometimes, the aldol addition product loses a molecule of water during the reaction to form an α,β-unsaturated ketone. This is called an aldol condensation. The aldol reaction was discovered independently by Charles-Adolphe Wurtz and by Alexander Porfyrevich Borodin in 1872. Borodin observed the aldol dimerization of 3-hydroxybutanal from acetaldehyde under acidic conditions. The aldol reaction is used widely in the large scale production of commodity chemicals such as pentaerythritol and in the pharmaceutical industry for the synthesis of optically pure drugs. For example, Pfizer's initial route to the heart disease drug Lipitor (INN: atorvastatin), approved in 1996, employed two aldol reactions, allowing access to multigram-scale quantities of the drug.

The aldol structural motif is especially common in polyketides, a class of natural products from which many pharmaceuticals are derived, including the potent immunosuppressant FK506, the tetracycline antibiotics, and the antifungal agent amphotericin B. Extensive research on the aldol reaction has produced highly efficient methods which enable the otherwise challenging synthesis of many polyketides in the laboratory.

Selected Picture

TaxolTotalSynthesisColor.png

Paclitaxel is an important drug used for the treatment of cancer. Its complex structure provided a challenging target for its total synthesis by the Nicolaou group. The colors indicate the approach they used.

Selected reaction

The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (often called a Wittig reagent) to give an alkene and triphenylphosphine oxide.

Wittig reaction

The Wittig reaction was discovered in 1954 by Georg Wittig, for which he was awarded the Nobel Prize in Chemistry in 1979. It is widely used in organic synthesis for the preparation of alkenes. It should not be confused with the Wittig rearrangement.

Wittig reactions are most commonly used to couple aldehydes and ketones to singly substituted phosphine ylides. With simple ylides this results in almost exclusively the Z-alkene product. In order to obtain the E-alkene, the Schlosser modification of the Wittig reaction can be performed.

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Selected Biography

Elias James Corey (born July 12, 1928) is a renowned American organic chemist. In 1990 he won the Nobel Prize in Chemistry "for his development of the theory and methodology of organic synthesis", specifically retrosynthetic analysis.[1][2] Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies, and has advanced the science of organic synthesis considerably. He was awarded the Japan Prize in 1989.

He was born "William" to Christian Lebanese immigrants in Methuen, Massachusetts, 30 miles north of Boston. His mother changed his name to "Elias" to honor his father who died eighteen months after the birth of his son. His widowed mother, brother, two sisters and an aunt and uncle all lived together in a spacious house- struggling through the depression. He attended Catholic elementary school and Lawrence public High School.[1]

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Organic chemistry Resources

  • MIT OpenCourseWare: Organic Chemistry I
  • Organic Chemistry Lectures, Videos and Text
  • Journal of Organic Chemistry (Table of Contents)
  • Organic Letters (Table of Contents)
  • Synlett
  • Synthesis
  • Organic Chemistry Portal - Recent Abstracts and (Name)Reactions
  • SynArchive - Total Syntheses and Named Reactions
  • Home of a full, online, peer-reviewed organic chemistry text.
  • Virtual Textbook of Organic Chemistry
  • Organic World Wide - A collection of Links
  • Roger Frost's Chemistry Teaching Tools - Organic Chemistry
  • Organic chemistry help
  • Organic Chemisty Tutor
  • Chemical Freeware on http://www.acdlabs.com
  • wikichemistry.org - chemistry you can edit
organic nomenclature
  • IUPAC Blue Book (organic nomenclature)
  • IUPAC ligand abbreviations (pdf)
Organic reactions
  • namedreactions
  • [2]
  • [3]

Lists

Organic chemistry Topics

Organic compound

Organic reaction

Functional Groups

Organic Reactions

According to the Reaction's Mechanism
  1. electrophilic addition or EA
  2. nucleophilic addition or NA
  3. radical addition or RA
  1. nucleophilic aliphatic substitution with SN1, SN2 and SNi reaction mechanisms
  2. nucleophilic aromatic substitution or NAS
  3. nucleophilic acyl substitution
  4. electrophilic substitution or ES
  5. electrophilic aromatic substitution or EAS
  6. radical substitution or RS
  1. 1,2-rearrangements
  2. pericyclic reactions
  3. metathesis

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References

  1. ^ E. J. Corey, X-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1995, ISBN 0-471-11594-0.
  2. ^ "The Logic of Chemical Synthesis: Multistep Synthesis of Complex Carbogenic Molecules (Nobel Lecture)" E.J. Corey, Angew. Chem. Int. Ed. Engl. 1991, 30, 455.
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