Typical acid dissociation constants Ka for -keto esters are !0!1 (pKa 11). -Keto ester: a ketone carbonyl is to the carbonyl group of the ester.Ī proton attached to the -carbon atom of a -keto ester is relatively acidic. The stabilized enolates derived from -keto esters are particularly useful. Ester enolates are important reagents in synthetic organic chemistry. The present chapter extends our study of carbanions to the enolate ions derived from esters. In Chapter 18 you learned that enolate ions-reactive intermediates generated from aldehydes and ketones-are nucleophilic, and that this property can be used to advantage as a method for carbon–carbon bond formation. The first was acetylide ion in Chapter 9, followed in Chapter 14 by organometallic compounds-Grignard reagents, for example-that act as sources of negatively polarized carbon.
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