Treatment of acetylcyclopentane (see Scheme Q10a) with NaOEt in ethanol at 25 °C results in formation of a major, thermodynamic enolate (Scheme Q10a). NaOEt Thermodynamic enolate +] ELOH 25 °C (Scheme Q10a) (a) Draw the structure of the thermodynamic enolate. (b) Explain why the enolate in answer (a) is the major enolate present in the equilibrium at room temperature. (c) Draw the product formed when the thermodynamic enolate (1 mole) reacts with ethyl acrylate (1 mole) (Scheme Q10c). OEt + NaOEt Thermodynamic enolate Product ETOH 25 °C C12H2003 (Scheme Q10c)
Treatment of acetylcyclopentane (see Scheme Q10a) with NaOEt in ethanol at 25 °C results in formation of a major, thermodynamic enolate (Scheme Q10a). NaOEt Thermodynamic enolate +] ELOH 25 °C (Scheme Q10a) (a) Draw the structure of the thermodynamic enolate. (b) Explain why the enolate in answer (a) is the major enolate present in the equilibrium at room temperature. (c) Draw the product formed when the thermodynamic enolate (1 mole) reacts with ethyl acrylate (1 mole) (Scheme Q10c). OEt + NaOEt Thermodynamic enolate Product ETOH 25 °C C12H2003 (Scheme Q10c)
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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10.
Answer ALL parts of this question.
Treatment of acetylcyclopentane (see Scheme Q10a) with NaOEt in ethanol at
25 °C results in formation of a major, thermodynamic enolate (Scheme Q10a).
NaOEt
Thermodynamic enolate
ELOH
25 °C
(Scheme Q10a)
(a) Draw the structure of the thermodynamic enolate.
(b) Explain why the enolate in answer (a) is the major enolate present in the
equilibrium at room temperature.
(C) Draw the product formed when the thermodynamic enolate (1 mole)
reacts with ethyl acrylate (1 mole) (Scheme Q10c).
OEt
+ NaOEt
Thermodynamic enolate
Product
ETOH
25 °C
C12H2003
(Scheme Q10c)
(d) Draw the kinetic product formed when 1-cyclopentene-1-carbaldehyde
reacts with sodium cyanide at low temperature (5 °C) and over a short
reaction time (5 minutes) (Scheme Q10d).
NACN
Kinetic product
ELOH
5 °C
(Scheme Q10d)
>
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