The Claisen condensation converts two molecules of an ester into a ß-keto ester. The reaction starts with the ester in an alkoxide/alcohol solution and is worked up with acid to form the neutral ß-keto ester product. eh 2 b 1. -OCH₂CH3 CH3CH₂OH 2. H₂O* Identify the mechanistic steps and intermediates of the Claisen condensation of ethyl ethanoate with ethoxide. Include all formal charges and non-bonding electrons. If an enolate resonance form is possible, draw only the carbanionic form. Tip: always omit ethanol byproducts. Step 1 is a deprotonation by ethoxide. Which proton is deprotonated? OH the methyl bonded to the carbonyl the methyl bonded to CH₂ the CH₂ group

The Claisen condensation converts two molecules of an ester into a ß-keto ester. The reaction starts with the ester in an alkoxide/alcohol solution and is worked up with acid to form the neutral ß-keto ester product. eh 2 b 1. -OCH₂CH3 CH3CH₂OH 2. H₂O* Identify the mechanistic steps and intermediates of the Claisen condensation of ethyl ethanoate with ethoxide. Include all formal charges and non-bonding electrons. If an enolate resonance form is possible, draw only the carbanionic form. Tip: always omit ethanol byproducts. Step 1 is a deprotonation by ethoxide. Which proton is deprotonated? OH the methyl bonded to the carbonyl the methyl bonded to CH₂ the CH₂ group

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…
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