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- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.07%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are more common, partially due to the thermodynamic stability of the C=O bonds in the final ...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the alpha carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will a racemic mixture of enantiomers.
- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_252_-_Organic_Chemistry_II/05%3A_Aldehydes_and_Ketones/5.04%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the f...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the α-carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will be a racemic mixture of enantiomers.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.06%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the f...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the α-carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will be a racemic mixture of enantiomers.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.06%3A_Reactivity_of_Enolate_IonsEnolate ions, which are nucleophilic species formed from carbonyl compounds with alpha-hydrogens, can engage in various reactions, such as alkylation and condensation, making them valuable in synthesi...Enolate ions, which are nucleophilic species formed from carbonyl compounds with alpha-hydrogens, can engage in various reactions, such as alkylation and condensation, making them valuable in synthesizing complex organic molecules. Their reactivity depends on the stability of the enolate formed, influenced by factors like substitution and resonance. Understanding enolate reactivity is essential for harnessing their potential in organic synthesis.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.07%3A_Reactivity_of_Enolate_IonsFigure 22.6: The electrostatic potential map of acetone enolate ion shows how the negative charge is delocalized over both the oxygen and the α carbon. As soon as a small amount of enolate is generate...Figure 22.6: The electrostatic potential map of acetone enolate ion shows how the negative charge is delocalized over both the oxygen and the α carbon. As soon as a small amount of enolate is generated, halogen reacts with it immediately, removing it from the reaction and driving the equilibrium toward further enolate ion formation. An α-halogenated ketone is generally more acidic than the starting, unsubstituted ketone because of the electron-withdrawing inductive effect of the halogen atom.
- https://chem.libretexts.org/Ancillary_Materials/Reference/Organic_Chemistry_Glossary/Haloform_ReactionThe haloform reaction is the reaction of a methyl ketone with chlorine, bromine, or iodine in the presence of hydroxide ions to give a carboxylate ion and a haloform. There is one aldehyde that under...The haloform reaction is the reaction of a methyl ketone with chlorine, bromine, or iodine in the presence of hydroxide ions to give a carboxylate ion and a haloform. There is one aldehyde that undergoes the haloform reaction, which is acetaldehyde.
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/06%3A_Carbonyl_Alpha-Substitution_Reactions/6.07%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the f...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the α-carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will be a racemic mixture of enantiomers.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.06%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the f...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the α-carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will be a racemic mixture of enantiomers.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/08%3A_Carbonyl_Alpha-Substitution_Reactions/8.07%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the f...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are much more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the α-carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will be a racemic mixture of enantiomers.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Reactivity_of_Alpha_Hydrogens/Alpha_HalogenationA carbonyl containing compound with α hydrogens can undergo a substitution reaction with halogens. This reaction comes about because of the tendency of carbonyl compounds to form enolates in basic c...A carbonyl containing compound with α hydrogens can undergo a substitution reaction with halogens. This reaction comes about because of the tendency of carbonyl compounds to form enolates in basic condition and enols in acidic condition. In these cases even weak bases, such as the hydroxide anion, is sufficient enough to cause the reaction to occur because it is not necessary for a complete conversion to the enolate.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)/17%3A_Carbonyl_Compounds_II-_Enols_and_Enolate_Anions._Unsaturated_and_Polycarbonyl_Compounds/17.03%3A_Halogenation_of_Aldehydes_and_KetonesHalogenation of saturated aldehydes and ketones usually occurs exclusively by replacement of hydrogens alpha to the carbonyl group. The reagents that commonly are used to halogenate carbonyl compounds...Halogenation of saturated aldehydes and ketones usually occurs exclusively by replacement of hydrogens alpha to the carbonyl group. The reagents that commonly are used to halogenate carbonyl compounds are those that are used to halogenate alkanes. However, the mechanism of the two types of halogenation normally are very different. When one attempts E2 reactions with α-halo ketones using strong bases such as alkoxides, an interesting rearrangement may occur called the Favorskii rearrangement
