H3C OEt H₂C 1. NaOEt, EtOH OEt 2. H₂O* H3C EtOH OEt Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to occur that forms a f-ketoester. This reaction is known as the Claisen condensation. The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a f-ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the x-carbon drives the reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 20 H3C EtO: X HH EtOH OEt H3C OEt H 7 a
H3C OEt H₂C 1. NaOEt, EtOH OEt 2. H₂O* H3C EtOH OEt Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to occur that forms a f-ketoester. This reaction is known as the Claisen condensation. The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a f-ketoester. The steps leading up to this point are all reversible. The best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the x-carbon drives the reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of the final product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 20 H3C EtO: X HH EtOH OEt H3C OEt H 7 a
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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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![H₂C
OEt
H₂C
OEt
1. NaOEt, EtOH
2. H₂O*
H₂C
EtOH
OEt
Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to
occur that forms a ẞ-ketoester. This reaction is known as the Claisen condensation.
The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ẞ-ketoester. The steps leading up to this point are all reversible. The
best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drives the
reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of
the final product.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
་་་་་་་
H3C
EtO:
HH
OEt
EtOH
H3C
OEt
H
7 a](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F99cec762-bb4f-4bc3-ab12-57eaa572f103%2Fe4891916-75a3-4992-ac8b-9f4b4a17db96%2F3or8anr_processed.jpeg&w=3840&q=75)
Transcribed Image Text:H₂C
OEt
H₂C
OEt
1. NaOEt, EtOH
2. H₂O*
H₂C
EtOH
OEt
Esters, like aldehydes and ketones, are weakly acidic. Treatment of an ester with 1 equivalent of a strong base, such as sodium ethoxide, causes a reversible carbonyl condensation to
occur that forms a ẞ-ketoester. This reaction is known as the Claisen condensation.
The tetrahedral intermediate thus formed expels an alkoxide leaving group to give an acyl substitution product, a ẞ-ketoester. The steps leading up to this point are all reversible. The
best yields for the Claisen condensation are obtained when the starting ester has more than one acidic a-hydrogen. In these cases, a second deprotonation of the a-carbon drives the
reaction equilibrium toward the product, thus requiring a full equivalent of base instead of a catalytic amount. Subsequent protonation with dilute aqueous acid resultsn a high yield of
the final product.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
་་་་་་་
H3C
EtO:
HH
OEt
EtOH
H3C
OEt
H
7 a
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