The Claisen condensation converts two molecules of an ester into a β-keto ester. The reaction starts with the ester in an alkoxide/alcohol solution and is worked up with acid to form the neutral β-keto ester product.**Reaction Scheme:**1. Starting with ethyl ethanoate in the presence of an ethoxide ion (⁻OCH₂CH₃ / CH₃CH₂OH)2. Acid workup with H₃O⁺The diagram illustrates the reaction of two ethyl ethanoate molecules forming a β-keto ester and ethanol byproduct.**Instructions:**Show the curved-arrow mechanism for the Claisen condensation of ethyl ethanoate treated with ethoxide ion. Include all formal charges and nonbonding electrons. In each step, draw only the species that react in that step. If an enolate resonance form is possible, draw only the carbanionic form. If a CHₓ group is being deprotonated, draw all H's on the reacting site.**Tip:** Always omit ethanol byproducts.

Base abstracts alpha proton of the ester to produce enolate. Enolate acts as a nucleophile which attacks on ester caebonyl of another molecule to form tetrahedral intermediate. This tetrahedral intermediate then collapse into product.

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The Claisen condensation converts two molecules of an ester into a B-keto ester. The reaction starts with the ester in an alkoxide/alcohol solution and is worked up with acid to form the neutral B-keto ester product. 1. OCH2CH3 / CH3CH2OH 2 OH 2. H3O* Show the curved-arrow mechanism for the Claisen condensation of ethyl ethanoate treated with ethoxide ion. Include all formal charges and nonbonding electrons. In each step, draw only the species that react in that step. If an enolate resonance form is possible, draw only the carbanionic form. If a CH, group is being deprotonated, draw all H's on the reacting site. Tip: always omit ethanol byproducts.

The Claisen condensation converts two molecules of an ester into a B-keto ester. The reaction starts with the ester in an alkoxide/alcohol solution and is worked up with acid to form the neutral B-keto ester product. 1. OCH2CH3 / CH3CH2OH 2 OH 2. H3O* Show the curved-arrow mechanism for the Claisen condensation of ethyl ethanoate treated with ethoxide ion. Include all formal charges and nonbonding electrons. In each step, draw only the species that react in that step. If an enolate resonance form is possible, draw only the carbanionic form. If a CH, group is being deprotonated, draw all H's on the reacting site. Tip: always omit ethanol byproducts.

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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Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

The Claisen condensation converts two molecules of an ester into a β-keto ester. The reaction starts with the ester in an alkoxide/alcohol solution and is worked up with acid to form the neutral β-keto ester product.

**Reaction Scheme:**

1. Starting with ethyl ethanoate in the presence of an ethoxide ion (⁻OCH₂CH₃ / CH₃CH₂OH)
2. Acid workup with H₃O⁺

The diagram illustrates the reaction of two ethyl ethanoate molecules forming a β-keto ester and ethanol byproduct.

**Instructions:**

Show the curved-arrow mechanism for the Claisen condensation of ethyl ethanoate treated with ethoxide ion. Include all formal charges and nonbonding electrons. In each step, draw only the species that react in that step. If an enolate resonance form is possible, draw only the carbanionic form. If a CHₓ group is being deprotonated, draw all H's on the reacting site.

**Tip:** Always omit ethanol byproducts.

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