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Encyclopedia > Enol

Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond. Enols and carbonyl compounds (such as ketones and aldehydes) are in fact isomers; this is called keto-enol tautomerism: An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... Hydroxide is a functional group consisting of oxygen and hydrogen: -O−H It has a charge of 1-. The term hydroxyl group is used when the functional group -OH is counted as a substituent of an organic compound. ... 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. ... In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a compound that contains this functional group. ... An aldehyde is either a functional group consisting of a terminal carbonyl group, or a compound containing a terminal carbonyl group. ... In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ... In organic chemistry, keto-enol tautomerism refers to an equilibrium between a ketone and an enol. ...

The enol form is shown on the left. It is usually unstable, does not survive long, and changes into the keto (ketone) form, shown on the right. This is because oxygen is more electronegative than carbon and thus forms stronger multiple bonds. Hence, a carbon-oxygen (carbonyl) double bond is more than twice as strong as a carbon-oxygen single bond, but a carbon-carbon double bond is weaker than two carbon-carbon single bonds. example of an enol File links The following pages link to this file: Enol ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... It has been suggested that this article or section be merged with electronegativity. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... A chemical bond is the physical phenomenon of chemical substances being held together by attraction of atoms to each other through sharing, as well as exchanging, of electrons -or electrostatic forces. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ...


Only in 1,3 dicarbonyl and 1,3,5 tricarbonyl compounds does the (mono)enol form predominate. This is because resonance and intramolecular hydrogen bonding occur in the enol form but are not possible for the keto form. Thus, propanedial (OHCCH2CHO) exists to an extent of over 99 percent as the monoenol. The proportion is lower for 1,3 aldehyde ketones and diketones. The enol (and enolate) are an important intermediate for many organic reactions. Resonance structures are diagrammatic tools in organic chemistry to symbolize resonant bonds between atoms in molecules. ... Snapshot from a simulation of liquid water. ...


The words enol and alkenol are combinations of the words alkene (or just -ene, the suffix given to alkenes) and alcohol (which represents the enol's hydroxyl group). The suffix -ene is used in organic chemistry to form names of organic compounds containing the -C=C- group: see olefin. ... An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon to carbon double bond. ... In chemistry, an alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom, which in turn is bound to other hydrogen and/or carbon atoms. ...


Enolate ion

When the hydroxyl group (−OH) in an enol loses a hydrogen ion (H+), a negative enolate ion is formed as shown here:

1,3 dicarbonyl and 1,3,5 tricarbonyl compounds are quite acidic because of the strong resonance stabilization created when one of the hydrogens is removed (from either the keto or enol forms). The resonance from the enol is exactly analgous to that used to explain the acidity of phenols and consists of the delocalisation of the negative charge of the enolate ion to the alpha-carbon. These enolate ions are very valuable in synthesis of complicated alcohols and carbonyl compounds (aldol additions). The synthetic value is due to the nucleophilicity of the enolate group, since it has a net negative charge. Wikipedia does not have an article with this exact name. ... In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-OH) attached to an aromatic hydrocarbon group. ... In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ...


  Results from FactBites:
 
Enol - Wikipedia, the free encyclopedia (496 words)
Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond.
Enols and carbonyl compounds (such as ketones and aldehydes) are in fact isomers; this is called keto-enol tautomerism:
The enol form is shown on the left.
Enol Summary (802 words)
Enols are the tautomeric isomers of certain ketones Enolates are the conjugate bases of enols and are important intermediates in both synthetic and biosynthetic chemistry, where the act as nucleophiles in many different substitution reactions..
The words enol and alkenol are combinations of the words alkene (or just -ene, the suffix given to alkenes) and alcohol (which represents the enol's hydroxyl group).
The resonance from the enol is exactly analogous to that used to explain the acidity of phenols and consists of the delocalisation of the negative charge of the enolate ion to the alpha-carbon.
  More results at FactBites »


 

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