Electron Distribution in Keto-Enol Tautomers

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Presentation transcript:

Electron Distribution in Keto-Enol Tautomers p. 696

Electron Distribution in Keto-Enol Tautomers Resonance Hybrid p. 696

Electron Distribution in Enolates Resonance Hybrid Figure 17.5 Mechanism of enolate ion formation by abstraction of an α proton from a carbonyl compound. The enolate ion is stabilized by resonance, and the negative charge (red) is shared by the oxygen and the carbon atom, as indicated by the electrostatic potential map. Fig. 17-5, p. 703

Table 17-1, p. 705

Figure 17.6 The electrostatic potential map of acetone enolate ion shows how the negative charge is delocalized over both the oxygen and the α carbon. As a result, two modes of reaction of an enolate ion with an electrophile E+ are possible. Reaction on carbon to yield an α-substituted carbonyl product is more common. Fig. 17-6, p. 707