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Encyclopedia > Carbonyl
Carbonyl group

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. Image File history File links Download high resolution version (789x741, 11 KB) Summary Description: Structural formula of a general carbonyl group (RCOR). Author, date of creation: self made by Ben Mills at 14:39, 8 March 2006 (UTC). ... Image File history File links Download high resolution version (789x741, 11 KB) Summary Description: Structural formula of a general carbonyl group (RCOR). Author, date of creation: self made by Ben Mills at 14:39, 8 March 2006 (UTC). ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... Properties In chemistry and physics, an atom (Greek ἄτομος or átomos meaning indivisible) is the smallest particle still characterizing a chemical element. ... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ...


The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl); in this situation, carbon is triple-bonded to oxygen : C≡O. Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a... Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ... Organometallic have classically been compounds having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. ... Metal carbonyls are organometallic complexes of transition metals with carbon monoxide. ... Nickel carbonyl, or tetracarbonylnickel is the compound Ni(CO)4. ... Covalently bonded hydrogen and carbon in a molecule of methane. ...


The remainder of this article concerns itself with the organic chemistry definition of carbonyl.


A carbonyl group characterizes the following types of compounds (where -CO denotes a C=O carbonyl group):

Compound Aldehyde Ketone Carboxylic acid Ester Amide Enone Acyl chloride Carboxylic anhydride
Structure
General formula RCHO RCOR' RCOOH RCOOR' RCONHR' RC(O)C(R')CR''R''' RCOCl (RCO)2O

Contents

An aldehyde. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... General formula of a carboxylate ester. ... Amide functional group In chemistry, an amide is one of two kinds of compounds: - the organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group (pictured to the right); or - a particular kind of nitrogen anion. ... An enone is an unsaturated chemical compound or functional group consisting of a conjugated system of an alkene and a ketone. ... General Chemical Structure of an Acyl Chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. ... Acid anhydrides have the general formula (RCO)2O, and appear to be the dehydration product of two carboxylic acid molecules. ... Image File history File links Download high resolution version (787x742, 9 KB) Summary Description: Structural formula of a general aldehyde group (RCHO). ... Image File history File links Download high resolution version (822x742, 10 KB) Summary Description: Structural formula of a general ketone (RCOR). Author, date of creation: self made by Ben Mills at 14:38, 8 March 2006 (UTC). ... Image File history File links Carboxylic-acid. ... Image File history File links Ester. ... Image File history File links Download high resolution version (1120x1044, 15 KB) Summary Description: Structural formula of a general amide group (RCONRR). ... Image File history File links Download high resolution version (1383x1044, 22 KB) Summary Description: Structural formula of a general enone group (RCOC(R)=CRR). Author, date of creation: self made by Ben Mills at 17:17, 8 March 2006 (UTC). ... Wikipedia does not have an article with this exact name. ... Image File history File links Download high resolution version (1347x744, 18 KB) Summary Description: Structural formula of a general anhydride group ((RCO)2O). ...

Reactivity

'''Oxygen is more electronegative than carbon, and thus pulls electron density away from carbon to increase the bond's polarity. Therefore, the carbonyl carbon becomes electrophilic, and thus more reactive with nucleophiles. Also, the electronegative oxygen can react with an electrophile; for example a proton in an acidic solution or other Lewis Acid. It has been suggested that this article or section be merged with electronegativity. ... The polarity of an object is, in general, its physical alignment of atoms. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ...


The alpha hydrogen in a carbonyl compound is much more acidic (~1030 times more acidic) than a typical CH bond. For example the pKa values of acetaldehyde and acetone are 16.7 and 19, respectively.[1] The alpha carbon in organic chemistry refers to the first carbon after the carbon that attaches to the functional group (the carbon is attached at the first, or alpha, position). ... R-phrases , , S-phrases , , , Flash point −39 °C Autoignition temperature 185 °C RTECS number AB1925000 Supplementary data page Structure and properties n, εr, etc. ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ...


Amides are the most stable of the carbonyl couplings due to their high resonance stabilization between the Nitrogen-Carbon and Carbon-Oxygen bonds.


Carbonyl groups can be reduced by reaction with hydride reagents such as NaBH4 and LiAlH4, and by organometallic reagents such as organolithium reagents and Grignard reagents. Illustration of a redox reaction Redox (shorthand for oxidation/reduction reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... A hydride is a compound of hydrogen with more electropositive elements. ... Organometallic have classically been compounds having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. ... An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ...


Other important reactions include:

The Wolff-Kishner reduction is a chemical reaction that fully reduces a ketone (or aldehyde) to an alkane. ... The Clemmensen reduction is a chemical reaction aimed at reducing carbonyl groups of aldehydes and ketones to -CH2- groups. ... An acetyl group that contains a sulfur atom (see thiol) This page is a candidate to be copied to Wiktionary. ... In chemistry, hydration is the condition of being combined with water. ... A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... A hemiacetal is a functional group or compound containing the function group in the form of: where R and R are any carbon backbones. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... An ketal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... Ammonia is a compound with the formula NH3. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ... Hydroxylamine is a reactive chemical with formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each. ... An oxime is one in a class of chemical compounds with the general formula R1R2 C N O H, where R1 is an organic side chain and R2 is either hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. ... The cyanide ion, CN−. From the top: 1. ... Cyanohydrin is any of several compounds that contain both the CN and OH radicals. ... Acyloins are a class of organic compounds in organic chemistry sharing a common functional group consisting of a hydroxyl group placed on the α-position of a carbonyl group. ... The Tebbe reagent is (C5H5)2TiCH2ClAl(CH3)2. ... 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. ... The chemical structure of ethylene, the simplest alkene. ... The Tishchenko reaction is a chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide. ... An Aldol condensation is an organic reaction where an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone followed by dehydration to a conjugated enone. ... The Cannizzaro reaction, named after Stanislao Cannizzaro, is a chemical reaction that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position. ...

α,β-Unsaturated carbonyl compounds

α,β-Unsaturated carbonyl compounds are an important class of carbonyl compounds with the general structure Cβ=Cα−C=O. In these compounds the carbonyl group is conjugated with an alkene (hence the adjective unsaturated), from which they derive special properties. Examples of unsaturated carbonyls are acrolein, mesityl oxide, acrylic acid and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction. The carbonyl group, be it an aldehyde or acid, draws electrons away from the alkene and the alkene group in unsaturated carbonyls are therefore deactived towards an electrophile such as bromine or hydrochloric acid. As a general rule with unsymmetric electrophiles hydrogen attaches itself at the α position in an electrophilic addition. On the other hand, these compounds are activated towards nucleophiles in nucleophilic addition. A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... The chemical structure of ethylene, the simplest alkene. ... In grammar, an adjective is a part of speech that modifies a noun or a pronoun, usually by describing it or making its meaning more specific. ... In chemistry, saturation has four different meanings: In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of that substance will appear as a precipitate. ... In organic chemistry, Acrolein or Propenal is the simplest unsaturated aldehyde, and it has a chemical formula of CH2=CHCHO. CAS number is 107-02-8. ... Mesityl oxide is a ketone with the formula CH3C(O)CH=C(CH3)2. ... Acrylic acid or prop-2-enoic acid is a chemical compound with the formula C3H4O2 and structure (which is sometimes abbreviated as CH2=CHCOOH). ... Maleic acid or (Z)-Butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). ... A typical experimental setup for an aldol reaction. ... The Perkin reaction is a chemical reaction developed by William Perkin that can be used to make cinnamic acids by the aldol condensation of aromatic aldehydes and acid anhydrides in the presence of an alkali salt of the acid. ... An aldehyde. ... Acidity redirects here. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). ... In organic chemistry, an electrophilic addition reaction is an addition reaction where in chemical compound a pi bond is removed by the creation of two new covalent bonds. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ...


Spectroscopy

  • Infrared spectroscopy: the C=O double bond absorbs infrared light at wavenumbers between approximately 1680–1750 cm−1. This absorption is known as the "carbonyl stretch" when displayed on an infrared absorption spectrum.
  • Nuclear magnetic resonance: the C=O double-bond exhibits different resonances depending on surrounding atoms, generally a downfield shift. The 13C NMR of a carbonyl carbon is in the range of 160-220 ppm.
  • Mass spectrometry

Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... Image of two girls in mid-infrared (thermal) light (false-color) Infrared (IR) radiation is electromagnetic radiation of a wavelength longer than that of visible light, but shorter than that of radio waves. ... Wavenumber in most physical sciences is a wave property inversely related to wavelength, having SI units of reciprocal meters (m−1). ... Pacific Northwest National Laboratorys high magnetic field (800 MHz, 18. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ...

Other organic carbonyl compounds

Urea is an organic compound of carbon, nitrogen, oxygen and hydrogen, with the formula CON2H4 or (NH2)2CO. Urea is also known as carbamide, especially in the recommended International Non-proprietary Names (rINN) in use in Europe. ... Carbamates are a group of organic compounds sharing a common functional group with the general structure -NH(CO)O-. More precisely the carbamate group is considered an amide group with an alkoxy or hydroxy functional group next to the carbonyl group. ...

Inorganic carbonyl compounds

Carbon dioxide is a chemical compound composed of one carbon and two oxygen atoms. ... Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references Carbonyl sulfide is a colourless gas at room temperature with an unpleasant odor. ... Phosgene (also known as carbonyl chloride, COCl2) is a highly toxic gas or refrigerated liquid that was used as a chemical weapon in World War I. It has no color, but is detectable in air by its odor, which resembles moldy hay. ...

See also

Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well...

References

Further reading

  • L.G. Wade, Jr. Organic Chemistry, 5th ed. Prentice Hall, 2002. ISBN 0-13-033832-X
  • The Frostburg State University Chemistry Department. Organic Chemistry Help (2000).
  • Advanced Chemistry Development, Inc. IUPAC Nomenclature of Organic Chemistry (1997).
  • William Reusch. VirtualText of Organic Chemistry (2004).
  • Purdue Chemistry Department [1] (retrieved Sep 2006). Includes water solubility data.

  Results from FactBites:
 
Nickel carbonyl - definition of Nickel carbonyl in Encyclopedia (126 words)
Nickel carbonyl - definition of Nickel carbonyl in Encyclopedia
Nickel carbonyl, or tetracarbonyl nickel is a covalent compound of nickel, which is, unusually for a metal compound, a colorless liquid at room temperature.
It is highly toxic and may be fatal if ingested or absorbed through the skin.
Awardees and Lecturers (286 words)
Professor Denmark is primarily interested in the invention of new synthetic reactions and the origin of stereocontrol in fundamental carbon-carbon bond forming reactions.
The current emphasis in his laboratories centers on the relationship between structure, reactivity and stereoselectivity in a variety of organo-element systems such as: palladium catalyzed cross-couplings with organofunctional silicon compounds, asymmetric catalysis of carbonyl addition reactions and chiral Lewis base activation of Lewis acids.
In addition his research program encompasses the development and application of tandem heterodiene cycloadditions for the synthesis of complex polycyclic alkaloids.
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