**Synthesis and Mechanism****Problem 7:****Preparation of the Compound**The compound shown below is synthesized using a mixture of formaldehyde and ethyl acetoacetate under basic conditions, followed by acid-catalyzed decarboxylation. Describe all the steps and mechanisms involved in the preparation of this compound.**Step-by-Step Mechanism:**1. **Initial Reactants:** - Formaldehyde (HCHO) - Ethyl acetoacetate (CH3COCO2Et)2. **Condensation Reaction:** a. The reaction begins with the formation of an enolate from ethyl acetoacetate under basic conditions. b. The enolate then reacts with formaldehyde through an aldol condensation, forming a β-hydroxy ester intermediate.3. **Aldol Condensation:** - The β-hydroxy ester undergoes dehydration (removal of water), resulting in the formation of a carbon-carbon double bond, leading to an α,β-unsaturated ester.4. **Cyclization:** - The condensation product undergoes intramolecular cyclization leading to the formation of a six-membered cyclic compound.5. **Decarboxylation:** a. The compound undergoes acid-catalyzed decarboxylation which removes the carboxyl group (CO2Et), resulting in the formation of the final compound.**Depicted Compound:** - A cyclic ketone with a methyl group (CH3) at one position and an ester group (CO2Et) at another position of the six-membered ring.**Mechanism Visualization:**The provided molecular structure in the image illustrates the final cyclic compound with its specific functional groups such as the ketone (carbonyl group) and ester (CO2Et group) attached to the cyclohexane ring.**Diagram Explanation:**- The hexagon represents a six-membered ring (cyclohexane) with a carbonyl group (C=O) and an ester group (CO2Et) attached.- Two double bonds are located within the ring indicating conjugation.- A methyl group (CH3) is attached to one carbon of the ring, and an ester group (CO2Et) is attached to the adjacent carbon.Understanding these mechanisms and the steps will help in comprehending how complex organic compounds can be synthesized using specific reactions and

Organic reactions are chemical reactions involving organic compounds . The basic organic…

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base, followed by acid-catalyzed decarboxylation. Write all steps and mechanism of each. CH3

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

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

**Synthesis and Mechanism**

**Problem 7:**
**Preparation of the Compound**

The compound shown below is synthesized using a mixture of formaldehyde and ethyl acetoacetate under basic conditions, followed by acid-catalyzed decarboxylation. Describe all the steps and mechanisms involved in the preparation of this compound.

**Step-by-Step Mechanism:**

1. **Initial Reactants:**
- Formaldehyde (HCHO)
- Ethyl acetoacetate (CH3COCO2Et)

2. **Condensation Reaction:**
a. The reaction begins with the formation of an enolate from ethyl acetoacetate under basic conditions.
b. The enolate then reacts with formaldehyde through an aldol condensation, forming a β-hydroxy ester intermediate.

3. **Aldol Condensation:**
- The β-hydroxy ester undergoes dehydration (removal of water), resulting in the formation of a carbon-carbon double bond, leading to an α,β-unsaturated ester.

4. **Cyclization:**
- The condensation product undergoes intramolecular cyclization leading to the formation of a six-membered cyclic compound.

5. **Decarboxylation:**
a. The compound undergoes acid-catalyzed decarboxylation which removes the carboxyl group (CO2Et), resulting in the formation of the final compound.

**Depicted Compound:**
- A cyclic ketone with a methyl group (CH3) at one position and an ester group (CO2Et) at another position of the six-membered ring.

**Mechanism Visualization:**
The provided molecular structure in the image illustrates the final cyclic compound with its specific functional groups such as the ketone (carbonyl group) and ester (CO2Et group) attached to the cyclohexane ring.

**Diagram Explanation:**
- The hexagon represents a six-membered ring (cyclohexane) with a carbonyl group (C=O) and an ester group (CO2Et) attached.
- Two double bonds are located within the ring indicating conjugation.
- A methyl group (CH3) is attached to one carbon of the ring, and an ester group (CO2Et) is attached to the adjacent carbon.

Understanding these mechanisms and the steps will help in comprehending how complex organic compounds can be synthesized using specific reactions 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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