Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Which enol form of ethyl 3-oxobutanoate is predominant at equilibrium?
K Your answer:
но
OEt
d)
Correct answer:
Он
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.
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Transcribed Image Text:Which enol form of ethyl 3-oxobutanoate is predominant at equilibrium? K Your answer: но OEt d) Correct answer: Он 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.
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