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2. Show the step(s) necessary to transform the compound on the left into the acid on the right. HOCH₂CH₂CH₂Br HOCH,CH,CH,COH

2. Show the step(s) necessary to transform the compound on the left into the acid on the right. HOCH₂CH₂CH₂Br HOCH,CH,CH,COH

Chemistry
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
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Question 2:** Show the step(s) necessary to transform the compound on the left into the acid on the right. **Compound Transformation:** - Initial Compound: HOCH₂CH₂CH₂Br - Desired Compound: HOCH₂CH₂CH₂COOH **Explanation:** In this problem, we are tasked with converting a bromine-containing alcohol into a carboxylic acid. The initial compound is 3-bromopropanol, and the target compound is 4-hydroxybutanoic acid. ### Steps for Transformation: 1. **Nucleophilic Substitution:** - Replace bromine (Br) with a carboxyl group precursor, such as a cyano group (CN) through an SN2 reaction. This can be achieved using sodium cyanide (NaCN) to form an intermediate nitrile. 2. **Hydrolysis:** - Convert the nitrile to a carboxylic acid by hydrolysis. This can be done using acidic or basic conditions: - **Acidic Hydrolysis:** Treat the nitrile with dilute hydrochloric acid (HCl) or sulfuric acid (H₂SO₄) and water. - **Basic Hydrolysis:** Use a base such as sodium hydroxide (NaOH) followed by an acidification step with HCl to obtain the carboxylic acid. Through these steps, the bromine atom is ultimately replaced by a carboxylic acid group, transforming the initial alcohol into the desired acid.
Transcribed Image Text:**Question 2:** Show the step(s) necessary to transform the compound on the left into the acid on the right. **Compound Transformation:** - Initial Compound: HOCH₂CH₂CH₂Br - Desired Compound: HOCH₂CH₂CH₂COOH **Explanation:** In this problem, we are tasked with converting a bromine-containing alcohol into a carboxylic acid. The initial compound is 3-bromopropanol, and the target compound is 4-hydroxybutanoic acid. ### Steps for Transformation: 1. **Nucleophilic Substitution:** - Replace bromine (Br) with a carboxyl group precursor, such as a cyano group (CN) through an SN2 reaction. This can be achieved using sodium cyanide (NaCN) to form an intermediate nitrile. 2. **Hydrolysis:** - Convert the nitrile to a carboxylic acid by hydrolysis. This can be done using acidic or basic conditions: - **Acidic Hydrolysis:** Treat the nitrile with dilute hydrochloric acid (HCl) or sulfuric acid (H₂SO₄) and water. - **Basic Hydrolysis:** Use a base such as sodium hydroxide (NaOH) followed by an acidification step with HCl to obtain the carboxylic acid. Through these steps, the bromine atom is ultimately replaced by a carboxylic acid group, transforming the initial alcohol into the desired acid.
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