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
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
Chemistry
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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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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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