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Relative rates of acid-catalyzed enolization for some ketones

The amount of enol present in equilibrium with a carbonyl group is a function of the substituent groups. In the case of compounds containing a single ketone, aldehyde, or ester function, there is almost none of the enol present at equilibrium. [Pg.317]

When two such groups are close to one another in a molecule, however, particularly if they are separated by a single carbon atom, a major amount of enol may be present. [Pg.318]

The enol forms of -diketones and jS-ketoesters are stabilized by intramolecular hydrogen bonding and conjugation of the carbon-carbon double bond with the other carbonyl group. Electron diffraction studies of the enol form of acetylacetone in the gas phase are consistent with a symmetrical structure having a linear O-H-O [Pg.318]

The accessibility of enolates and enols in, respectively, basic and acidic solutions of carbonyl compounds makes possible a wide range of reactions that depend on the nucleophilicity of such species. The reactions of enolates as nucleophiles in SN2-type processes will be discussed in Part B, Chapter 1. Enols and enolates can also act as nucleophiles toward carbonyl centers. These reactions are a major topic in Part B, Chapter 2. Both these classes of reactions are of fundamental importance in the construction of carbon frameworks in organic synthesis. [Pg.319]

Amino substituents on a carbon-carbon double bond also enhance the nucleophilicity at the -carbon—even more than enols. Such compounds are called enamines. Their preparation and reactions will be discussed in Chapter 8 and in Part B, Chapter 1. [Pg.319]


Table 7.11. Relative Rates of Acid-Catalyzed Enolization for Some Ketones"... Table 7.11. Relative Rates of Acid-Catalyzed Enolization for Some Ketones"...
Relative rates of acid-catalyzed enolization for some ketones... [Pg.812]




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Acidity of enols

Acidity of ketones

Acids relative

Enol ketones

Enolic acids

Enolization acid catalyzed

Enolization, of ketones

Enols acidity

Enols ketonization

For ketones

Ketone acid-catalyzed

Ketone enolate

Ketone enolates

Ketones enolization

Ketonization-enolization

Rate of acids

Rate of enolization

Relative rates

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