**Title: Malonic Ester Synthesis of Carboxylic Acids****Objective:**Outline all steps in a malonic ester synthesis of the following compounds:- (a) Pentanoic acid- (b) 2-Methylpentanoic acid- (c) 4-Methylpentanoic acid---**Introduction:**Malonic ester synthesis is a well-known method in organic chemistry for synthesizing carboxylic acids. This process utilizes malonic ester as a key starting material to create a wide array of substituted carboxylic acids through alkylation and subsequent decarboxylation. Here, we detail the steps required to synthesize specific carboxylic acids using this method.**Steps of Malonic Ester Synthesis:**1. **Formation of Enolate Anion:** - Begin by deprotonating the malonic ester with a strong base such as sodium ethoxide (NaOEt) to form an enolate anion.2. **Alkylation:** - The enolate anion acts as a nucleophile and undergoes alkylation by reacting with an appropriate alkyl halide. - For each compound: - **(a) Pentanoic acid:** Utilize a 1-bromo-3-pentane molecular fragment. - **(b) 2-Methylpentanoic acid:** Use a 2-bromo-2-methylbutane molecular fragment. - **(c) 4-Methylpentanoic acid:** Employ a 1-bromo-4-methylpentane fragment.3. **Hydrolysis and Decarboxylation:** - The alkylated malonic ester is subjected to acidic hydrolysis to convert the ester groups into carboxylic acid groups. - Heat the product to induce decarboxylation, removing one of the two carboxylic acid groups and forming the desired carboxylic acid.**Final Note:**This method is valuable for synthesizing substituted and straightforward carboxylic acids efficiently and is predominantly used in laboratory settings for research and educational applications.---

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Answered: Outline all steps in a malonic ester…

Outline all steps in a malonic ester synthesis of each of the following: (a) pentanoic acid, ) 2-methylpentanoic acid, and (c) 4-methylpentanoic acid.

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

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Question

**Title: Malonic Ester Synthesis of Carboxylic Acids**

**Objective:**
Outline all steps in a malonic ester synthesis of the following compounds:
- (a) Pentanoic acid
- (b) 2-Methylpentanoic acid
- (c) 4-Methylpentanoic acid

---

**Introduction:**

Malonic ester synthesis is a well-known method in organic chemistry for synthesizing carboxylic acids. This process utilizes malonic ester as a key starting material to create a wide array of substituted carboxylic acids through alkylation and subsequent decarboxylation. Here, we detail the steps required to synthesize specific carboxylic acids using this method.

**Steps of Malonic Ester Synthesis:**

1. **Formation of Enolate Anion:**
- Begin by deprotonating the malonic ester with a strong base such as sodium ethoxide (NaOEt) to form an enolate anion.

2. **Alkylation:**
- The enolate anion acts as a nucleophile and undergoes alkylation by reacting with an appropriate alkyl halide.
- For each compound:
- **(a) Pentanoic acid:** Utilize a 1-bromo-3-pentane molecular fragment.
- **(b) 2-Methylpentanoic acid:** Use a 2-bromo-2-methylbutane molecular fragment.
- **(c) 4-Methylpentanoic acid:** Employ a 1-bromo-4-methylpentane fragment.

3. **Hydrolysis and Decarboxylation:**
- The alkylated malonic ester is subjected to acidic hydrolysis to convert the ester groups into carboxylic acid groups.
- Heat the product to induce decarboxylation, removing one of the two carboxylic acid groups and forming the desired carboxylic acid.

**Final Note:**
This method is valuable for synthesizing substituted and straightforward carboxylic acids efficiently and is predominantly used in laboratory settings for research and educational applications.

---

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