Which enol form of ethyl 3-oxobutanoate is predominant at equilibrium? K Your answer: но OEt d) Correct answer: OH OEt b) Feedback: For enolate ions of 1,3-dicarbonyl compounds, see pp. 392-393. Conjugation of the C=C double bond with the remaining carbonyl provides a more stable enol, which rules out (a). Enols (b)-(d) may all be obtained by protonation of the same enolate or the readily interconverting stereoisomeric enolates. Of these, (b) and (d) allow stabilizing intramolecular hydrogen bonding; (b) is the more stable of the two owing to the conjugative stability of the remaining ester group.

Which enol form of ethyl 3-oxobutanoate is predominant at equilibrium? K Your answer: но OEt d) Correct answer: OH OEt b) Feedback: For enolate ions of 1,3-dicarbonyl compounds, see pp. 392-393. Conjugation of the C=C double bond with the remaining carbonyl provides a more stable enol, which rules out (a). Enols (b)-(d) may all be obtained by protonation of the same enolate or the readily interconverting stereoisomeric enolates. Of these, (b) and (d) allow stabilizing intramolecular hydrogen bonding; (b) is the more stable of the two owing to the conjugative stability of the remaining ester group.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 69GP

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