Malonic ester synthesis 4. Write the reaction showing all intermediates when H₂C(CO₂Et)2 (diethyl malonate) is reacted with NaOEt followed by 1) ethyl iodide; 2) NaOH; 3) H3O*; 4) A. Hint: Remember that B-oxo carboxylic undergo decarboxylation (loss of 1 equivalent of CO₂) when strongly heated. acids

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**Malonic Ester Synthesis**

**Question 4:**

Write the reactions showing all intermediates when H(COOC₂H₅)₂ (diethyl malonate) is reacted with:

1. NaOEt
2. Ethyl iodide
3. NaOH
4. H₃O⁺
5. Heat (Δ)

**Hint:** Remember that β-keto carboxylic acids undergo decarboxylation (loss of 1 equivalent of CO₂) when strongly heated.

---

**Explanation:**

This question pertains to the malonic ester synthesis, a method used to form substituted acetic acids. The process involves multiple steps:

1. **NaOEt (Sodium Ethoxide):** Acts as a base to deprotonate diethyl malonate, forming a carbanion.
2. **Ethyl Iodide:** Alkylates the ester via the carbanion, introducing an alkyl group.
3. **NaOH (Sodium Hydroxide):** Hydrolyzes the esters to a dicarboxylic acid.
4. **H₃O⁺ (Acid):** Protonates the dicarboxylate anion, giving the free diacid form.
5. **Heat (Δ):** Causes decarboxylation, resulting in the formation of a β-keto acid that loses CO₂ to form a ketone.

These steps illustrate the transformation of diethyl malonate into a substituted acetic acid derivative via decarboxylation.
Transcribed Image Text:**Malonic Ester Synthesis** **Question 4:** Write the reactions showing all intermediates when H(COOC₂H₅)₂ (diethyl malonate) is reacted with: 1. NaOEt 2. Ethyl iodide 3. NaOH 4. H₃O⁺ 5. Heat (Δ) **Hint:** Remember that β-keto carboxylic acids undergo decarboxylation (loss of 1 equivalent of CO₂) when strongly heated. --- **Explanation:** This question pertains to the malonic ester synthesis, a method used to form substituted acetic acids. The process involves multiple steps: 1. **NaOEt (Sodium Ethoxide):** Acts as a base to deprotonate diethyl malonate, forming a carbanion. 2. **Ethyl Iodide:** Alkylates the ester via the carbanion, introducing an alkyl group. 3. **NaOH (Sodium Hydroxide):** Hydrolyzes the esters to a dicarboxylic acid. 4. **H₃O⁺ (Acid):** Protonates the dicarboxylate anion, giving the free diacid form. 5. **Heat (Δ):** Causes decarboxylation, resulting in the formation of a β-keto acid that loses CO₂ to form a ketone. These steps illustrate the transformation of diethyl malonate into a substituted acetic acid derivative via decarboxylation.
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