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  Acidity of a C–H Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Acidity of α C-H

Many of the most helpful alpha-substitution reactions of ketones carried on by way of enolate anion conjugate bases. Because simple ketones are weaker acids than water, their enolate anions are essentially prepared by reaction with exceptionally strong bases in non-hydroxylic solvents. The Esters and nitriles are even weaker alpha-carbon acids than ketones (by over ten thousand times), however their enolate anions might be prepared and employed in a identical way. The existence of additional activating carbonyl functions increases the acidity of the alpha-hydrogens considerably, so that less stringent conditions may be employed for enolate anion formation. The effect of several carbonyl and related functional groups on the equilibrium acidity of alpha-hydrogen atoms (colored red in the diagram) is shortened in the table. For general reference, these acidity values have all been extrapolated to water solution, although the conjugate bases of those compounds having pKas greater than 18 will not have an important concentration in water solution.

To demonstrate the general nucleophilic reactivity of di-activated enolate anions, two instances of SN2 alkylation reactions are displayed below. Acetoacetic acid esters and Malonic acid esters are generally used starting materials and their usefulness in synthesis will be illustrated later. Note: each of these compounds has two acidic alpha-hydrogen atoms (colored red in the diagram). In the equations written here only one of these hydrogens is substituted; Though, the second is also acidic and a second alkyl substitution may be carried out in a identical way.

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