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- Keto–enol_tautomerism abstract "In organic chemistry, keto–enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) and an enol (an alcohol). The enol and keto forms are said to be tautomers of each other. The interconversion of the two forms involves the movement of an alpha hydrogen and the shifting of bonding electrons; hence, the isomerism qualifies as tautomerism.A compound containing a carbonyl group (C=O) is normally in rapid equilibrium with an enol tautomer, which contains a pair of doubly bonded carbon atoms adjacent to a hydroxyl (−OH) group, C=C-OH. The keto form predominates at equilibrium for most ketones. Nonetheless, the enol form is important for some reactions. The deprotonated intermediate in the interconversion of the two forms, referred to as an enolate anion, is important in carbonyl chemistry, in large part because it is a strong nucleophile.Normally, the keto–enol tautomerization chemical equilibrium is highly thermodynamically driven, and at room temperature the equilibrium heavily favors the formation of the keto form. A classic example for favoring the keto form can be seen in the equilibrium between vinyl alcohol and acetaldehyde (K = [enol]/[keto] ≈ 3 × 10−7). However, it is reported that in the case of vinyl alcohol, formation of a stabilized enol form can be accomplished by controlling the water concentration in the system and utilizing the kinetic favorability of the deuterium produced kinetic isotope effect (kH+/kD+ = 4.75, kH2O/kD2O = 12). Deuterium stabilization can be accomplished through hydrolysis of a ketene precursor in the presence of a slight stoichiometric excess of heavy water (D2O). Studies show that the tautomerization process is significantly inhibited at ambient temperatures ( kt ≈ 10−6 M/s), and the half life of the enol form can easily be increased to t1/2 = 42 minutes for first order hydrolysis kinetics.".
- Keto–enol_tautomerism thumbnail Keto-Enol-Tautomerie.png?width=300.
- Keto–enol_tautomerism wikiPageID "599134".
- Keto–enol_tautomerism wikiPageLength "7933".
- Keto–enol_tautomerism wikiPageOutDegree "63".
- Keto–enol_tautomerism wikiPageRevisionID "701111277".
- Keto–enol_tautomerism wikiPageWikiLink Acetaldehyde.
- Keto–enol_tautomerism wikiPageWikiLink Acid.
- Keto–enol_tautomerism wikiPageWikiLink Adamantane.
- Keto–enol_tautomerism wikiPageWikiLink Alcohol.
- Keto–enol_tautomerism wikiPageWikiLink Aldehyde.
- Keto–enol_tautomerism wikiPageWikiLink Antibonding_molecular_orbital.
- Keto–enol_tautomerism wikiPageWikiLink Aqueous_solution.
- Keto–enol_tautomerism wikiPageWikiLink Aromaticity.
- Keto–enol_tautomerism wikiPageWikiLink Base_(chemistry).
- Keto–enol_tautomerism wikiPageWikiLink Benzene.
- Keto–enol_tautomerism wikiPageWikiLink Biochemistry.
- Keto–enol_tautomerism wikiPageWikiLink Carbonyl.
- Keto–enol_tautomerism wikiPageWikiLink Category:Organic_reactions.
- Keto–enol_tautomerism wikiPageWikiLink Chemical_equilibrium.
- Keto–enol_tautomerism wikiPageWikiLink DNA.
- Keto–enol_tautomerism wikiPageWikiLink Deuterium.
- Keto–enol_tautomerism wikiPageWikiLink Diastereomer.
- Keto–enol_tautomerism wikiPageWikiLink Diisopropyl_ether.
- Keto–enol_tautomerism wikiPageWikiLink Electron.
- Keto–enol_tautomerism wikiPageWikiLink Emil_Erlenmeyer.
- Keto–enol_tautomerism wikiPageWikiLink Enantiomer.
- Keto–enol_tautomerism wikiPageWikiLink Enol.
- Keto–enol_tautomerism wikiPageWikiLink Francis_Crick.
- Keto–enol_tautomerism wikiPageWikiLink Guanine.
- Keto–enol_tautomerism wikiPageWikiLink Half-life.
- Keto–enol_tautomerism wikiPageWikiLink Heavy_water.
- Keto–enol_tautomerism wikiPageWikiLink History_of_molecular_biology.
- Keto–enol_tautomerism wikiPageWikiLink Hydroxyl.
- Keto–enol_tautomerism wikiPageWikiLink Hyperconjugation.
- Keto–enol_tautomerism wikiPageWikiLink Isomer.
- Keto–enol_tautomerism wikiPageWikiLink James_Watson.
- Keto–enol_tautomerism wikiPageWikiLink Jerry_Donohue.
- Keto–enol_tautomerism wikiPageWikiLink Ketene.
- Keto–enol_tautomerism wikiPageWikiLink Ketone.
- Keto–enol_tautomerism wikiPageWikiLink Kinetic_isotope_effect.
- Keto–enol_tautomerism wikiPageWikiLink Markovnikovs_rule.
- Keto–enol_tautomerism wikiPageWikiLink Metallocene.
- Keto–enol_tautomerism wikiPageWikiLink Naphthalene.
- Keto–enol_tautomerism wikiPageWikiLink Nucleophile.
- Keto–enol_tautomerism wikiPageWikiLink Nucleotide.
- Keto–enol_tautomerism wikiPageWikiLink Organic_chemistry.
- Keto–enol_tautomerism wikiPageWikiLink Phenol.
- Keto–enol_tautomerism wikiPageWikiLink Phosphoenolpyruvic_acid.
- Keto–enol_tautomerism wikiPageWikiLink Rate_equation.
- Keto–enol_tautomerism wikiPageWikiLink Reaction_mechanism.
- Keto–enol_tautomerism wikiPageWikiLink Recrystallization_(chemistry).
- Keto–enol_tautomerism wikiPageWikiLink Solution.
- Keto–enol_tautomerism wikiPageWikiLink Stereocenter.
- Keto–enol_tautomerism wikiPageWikiLink Stereochemistry_of_ketonization_of_enols_and_enolates.
- Keto–enol_tautomerism wikiPageWikiLink Tautomer.
- Keto–enol_tautomerism wikiPageWikiLink Thermodynamic_versus_kinetic_reaction_control.
- Keto–enol_tautomerism wikiPageWikiLink Thymine.
- Keto–enol_tautomerism wikiPageWikiLink Toluene.
- Keto–enol_tautomerism wikiPageWikiLink Trifluoroacetic_acid.
- Keto–enol_tautomerism wikiPageWikiLink Vinyl_alcohol.
- Keto–enol_tautomerism wikiPageWikiLink File:Keto-Enol-Tautomerie.png.
- Keto–enol_tautomerism wikiPageWikiLink File:Keto-enol.svg.
- Keto–enol_tautomerism wikiPageWikiLink File:Tetrahydronaphthalenedione.png.
- Keto–enol_tautomerism wikiPageWikiLinkText "Keto–enol tautomerism".
- Keto–enol_tautomerism wikiPageWikiLinkText "enolizaton".
- Keto–enol_tautomerism wikiPageWikiLinkText "keto and enol forms".
- Keto–enol_tautomerism wikiPageWikiLinkText "keto".
- Keto–enol_tautomerism wikiPageWikiLinkText "keto-enol tautomerism".
- Keto–enol_tautomerism wikiPageWikiLinkText "keto–enol tautomerism".
- Keto–enol_tautomerism wikiPageWikiLinkText "tautomerization".
- Keto–enol_tautomerism wikiPageUsesTemplate Template:Reflist.
- Keto–enol_tautomerism subject Category:Organic_reactions.
- Keto–enol_tautomerism type Reaction.
- Keto–enol_tautomerism comment "In organic chemistry, keto–enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) and an enol (an alcohol). The enol and keto forms are said to be tautomers of each other.".
- Keto–enol_tautomerism label "Keto–enol tautomerism".
- Keto–enol_tautomerism sameAs Q164917.
- Keto–enol_tautomerism sameAs Erlenmeyer-Regel.
- Keto–enol_tautomerism sameAs Keto-enooltautomeeria.
- Keto–enol_tautomerism sameAs توتومری_کتو-انول.
- Keto–enol_tautomerism sameAs Keto-enolitautomeria.
- Keto–enol_tautomerism sameAs Tautomeria_cheto-enolica.
- Keto–enol_tautomerism sameAs ケト-エノール互変異性.
- Keto–enol_tautomerism sameAs Keto-enoltautomerie.
- Keto–enol_tautomerism sameAs Tautomerismo_ceto-enol.
- Keto–enol_tautomerism sameAs m.02v291.
- Keto–enol_tautomerism sameAs Keto-enolni_tautomerizam.
- Keto–enol_tautomerism sameAs Keto-enolna_tavtomerija.
- Keto–enol_tautomerism sameAs Keto-enolni_tautomerizam.
- Keto–enol_tautomerism sameAs Q164917.
- Keto–enol_tautomerism sameAs 酮-烯醇互变异构.
- Keto–enol_tautomerism wasDerivedFrom Keto–enol_tautomerism?oldid=701111277.
- Keto–enol_tautomerism depiction Keto-Enol-Tautomerie.png.
- Keto–enol_tautomerism isPrimaryTopicOf Keto–enol_tautomerism.