8. The Stork enamine reaction and the intramolecular aldol reaction can be carried out in sequence to allow the synthesis of cyclohexenones. For example, reaction of the pyrrolidine enamine of cyclohexanone with 3-buten-2-one, followed by enamine hydrolysis and base treatment, yields the product indicated. Write each step, and show the mechanism of each. 1. H,C=CHCOCH3. 2. H30* 3. NaOH, H20

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**Title: Enamine Reactions in Cyclohexenone Synthesis**

**Introduction:**

In this lesson, we will explore the application of the Stork enamine reaction and the intramolecular aldol reaction in the synthesis of cyclohexenones. This process is an excellent example of a multi-step organic synthesis that integrates several reaction mechanisms to produce complex molecular structures.

**Step-by-Step Process:**

**Step 1: The Stork Enamine Reaction**

The Stork enamine reaction begins with the formation of an enamine from a secondary amine (pyrrolidine) and a ketone (cyclohexanone). This enamine then reacts with an α,β-unsaturated carbonyl compound (3-buten-2-one), facilitating a Michael addition reaction.

**Step 2: Enamine Hydrolysis**

After the Michael addition, the enamine undergoes hydrolysis in an acidic environment to regenerate the carbonyl compound while incorporating the newly added group into the cyclohexanone framework.

**Step 3: Intramolecular Aldol reaction**

The resulting compound is then subjected to basic conditions (NaOH in water), which promotes the formation of an enolate ion. This enolate ion undergoes an intramolecular aldol condensation, leading to the formation of a cyclohexenone structure.

**Diagrams Explanation:**

**Diagram 1: Reactants and Reaction Conditions**

The diagram shows the enamine of cyclohexanone and the reactant 3-buten-2-one. The reaction conditions are as follows:
1. \( \text{H}_2\text{C}=\text{CHCOCH}_3 \)
2. \( \text{H}_3\text{O}^+ \)
3. \( \text{NaOH, H}_2\text{O} \)

**Diagram 2: Final Product**

The final product is a cyclohexenone structure indicating ring formation and double-bond positioning within the ring.

**Summary:**

This sequence of reactions demonstrates the utility of the Stork enamine reaction followed by sequential hydrolysis and intramolecular aldol reaction to synthesize cyclohexenones. By understanding and applying these reactions, chemists can efficiently construct complex cyclic structures from simpler molecules, showcasing the power of organic synthesis in creating valuable chemical compounds.

---

This detailed breakdown provides a clear narrative of the reactions involved for educational purposes, guiding students
Transcribed Image Text:**Title: Enamine Reactions in Cyclohexenone Synthesis** **Introduction:** In this lesson, we will explore the application of the Stork enamine reaction and the intramolecular aldol reaction in the synthesis of cyclohexenones. This process is an excellent example of a multi-step organic synthesis that integrates several reaction mechanisms to produce complex molecular structures. **Step-by-Step Process:** **Step 1: The Stork Enamine Reaction** The Stork enamine reaction begins with the formation of an enamine from a secondary amine (pyrrolidine) and a ketone (cyclohexanone). This enamine then reacts with an α,β-unsaturated carbonyl compound (3-buten-2-one), facilitating a Michael addition reaction. **Step 2: Enamine Hydrolysis** After the Michael addition, the enamine undergoes hydrolysis in an acidic environment to regenerate the carbonyl compound while incorporating the newly added group into the cyclohexanone framework. **Step 3: Intramolecular Aldol reaction** The resulting compound is then subjected to basic conditions (NaOH in water), which promotes the formation of an enolate ion. This enolate ion undergoes an intramolecular aldol condensation, leading to the formation of a cyclohexenone structure. **Diagrams Explanation:** **Diagram 1: Reactants and Reaction Conditions** The diagram shows the enamine of cyclohexanone and the reactant 3-buten-2-one. The reaction conditions are as follows: 1. \( \text{H}_2\text{C}=\text{CHCOCH}_3 \) 2. \( \text{H}_3\text{O}^+ \) 3. \( \text{NaOH, H}_2\text{O} \) **Diagram 2: Final Product** The final product is a cyclohexenone structure indicating ring formation and double-bond positioning within the ring. **Summary:** This sequence of reactions demonstrates the utility of the Stork enamine reaction followed by sequential hydrolysis and intramolecular aldol reaction to synthesize cyclohexenones. By understanding and applying these reactions, chemists can efficiently construct complex cyclic structures from simpler molecules, showcasing the power of organic synthesis in creating valuable chemical compounds. --- This detailed breakdown provides a clear narrative of the reactions involved for educational purposes, guiding students
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