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- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_252_-_Organic_Chemistry_II/05%3A_Aldehydes_and_Ketones/5.01%3A_Keto-Enol_TautomerismThe positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electro...The positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_TautomerismThis causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The positioning of the enol and the car...This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The positioning of the enol and the carbonyl prevents the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_TautomerismThe page on keto-enol tautomerism describes the equilibrium between keto (carbonyl) and enol (alkene with an alcohol) forms of carbonyl compounds. This process involves the transfer of a proton and th...The page on keto-enol tautomerism describes the equilibrium between keto (carbonyl) and enol (alkene with an alcohol) forms of carbonyl compounds. This process involves the transfer of a proton and the movement of a double bond, affecting the compound's reactivity and stability. Factors like solvent and temperature can influence the tautomeric ratio. Understanding this equilibrium is crucial for predicting reaction outcomes in organic synthesis.
- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_250%3A_Organic_Chemistry_I/03%3A_Acids_and_Bases/3.06%3A_Keto-Enol_TautomerismThe positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. First, pi bond electrons f...The positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. First, pi bond electrons from the carbon in the alpha position attack the electrophilic H + provided by acid catalyst causing one of the lone pairs of electrons on the oxygen to form a pi bond to carbon generating a carbonyl.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.02%3A_Keto-Enol_TautomerismThis also causes the pi bond electrons from the enol double bond to attack the electrophilic H + provided by acid catalyst forming a C-H bond in the α-position This produced oxonium intermediate is su...This also causes the pi bond electrons from the enol double bond to attack the electrophilic H + provided by acid catalyst forming a C-H bond in the α-position This produced oxonium intermediate is subsequently deprotonated to form the neutral ketone and regenerate the acid catalyst. The positioning of the enol and the carbonyl prevents the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.02%3A_Keto-Enol_TautomerismFigure 22.2 MECHANISM Mechanism of enol formation under both acid-catalyzed and base-catalyzed conditions. (a) Acid catalysis involves (1) initial protonation of the carbonyl oxygen followed by (2) re...Figure 22.2 MECHANISM Mechanism of enol formation under both acid-catalyzed and base-catalyzed conditions. (a) Acid catalysis involves (1) initial protonation of the carbonyl oxygen followed by (2) removal of H + from the α position. (b) Base catalysis involves (1) initial deprotonation of the α position to give an enolate ion, followed by (2) reprotonation on oxygen.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/08%3A_Carbonyl_Alpha-Substitution_Reactions/8.02%3A_Keto-Enol_TautomerismThe positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electro...The positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The presence of two methyl groups on one of the α-carbons of the carbonyl means that the two hydrogens on the other α-carbon may be deprotonated to form an enolate.
- https://chem.libretexts.org/Courses/University_of_Connecticut/Chem_2444%3A_(Second_Semester_Organic_Chemistry)_UConn/10%3A_Reactions_at_the_Alpha-Carbon_(Alpha_Substitutions)/10.01%3A_Keto-Enol_TautomerismThe positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. First, pi bond electrons f...The positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. First, pi bond electrons from the carbon in the alpha position attack the electrophilic H + provided by acid catalyst causing one of the lone pairs of electrons on the oxygen to form a pi bond to carbon generating a carbonyl.
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/06%3A_Carbonyl_Alpha-Substitution_Reactions/6.02%3A_Keto-Enol_TautomerismThe positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electro...The positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst.
