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Determine the product(s) of the following substitution reaction: NaH :Br:

Determine the product(s) of the following substitution reaction: NaH :Br:

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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## Determine the Product(s) of the Following Substitution Reaction ### Reaction Scheme: **Reactants:** - The given reactant is a molecule consisting of a four-carbon chain with a hydroxyl group (OH) and a bromine atom (Br) attached to the second carbon. **Reagent:** - Sodium hydride (NaH) is used as a reagent in this reaction. **Process:** 1. The hydroxyl group (OH) is prone to deprotonation by NaH, forming an alkoxide ion. 2. The alkoxide ion, a strong nucleophile, then displaces the bromine atom through an intramolecular nucleophilic substitution reaction. ### Detailed Explanation: - **Step 1: Deprotonation** - The sodium hydride (NaH) reagent introduces a hydride ion (H⁻), which abstracts the proton (H⁺) from the hydroxyl group, resulting in the formation of water (H2O) and a negatively charged alkoxide ion (RO⁻). - **Step 2: Intramolecular Substitution** - The negatively charged alkoxide ion (RO⁻) formed in the first step acts as a nucleophile. It attacks the carbon bonded to the bromine atom, leading to the expulsion of the bromide ion (Br⁻) and the formation of a new carbon-oxygen bond. ### Expected Product: The product of this reaction is typically an epoxide (a three-membered ether ring), formed by the intramolecular attack of the alkoxide ion on the carbon atom bearing the leaving group (bromide). The structure of the resulting epoxide involves the oxygens forming a ring with the two adjacent carbons that were part of the initial four-carbon chain. ### Conclusion: The described process transforms the starting material (4-bromo-2-butanol) using sodium hydride in a substitution reaction to produce an epoxide. --- This content outlines a substitution reaction mechanism in organic chemistry, typically covered in undergraduate-level courses. It includes a thorough explanation of the chemical processes involved, making it suitable for students seeking to understand the reaction pathway and the product formation.
Transcribed Image Text:## Determine the Product(s) of the Following Substitution Reaction ### Reaction Scheme: **Reactants:** - The given reactant is a molecule consisting of a four-carbon chain with a hydroxyl group (OH) and a bromine atom (Br) attached to the second carbon. **Reagent:** - Sodium hydride (NaH) is used as a reagent in this reaction. **Process:** 1. The hydroxyl group (OH) is prone to deprotonation by NaH, forming an alkoxide ion. 2. The alkoxide ion, a strong nucleophile, then displaces the bromine atom through an intramolecular nucleophilic substitution reaction. ### Detailed Explanation: - **Step 1: Deprotonation** - The sodium hydride (NaH) reagent introduces a hydride ion (H⁻), which abstracts the proton (H⁺) from the hydroxyl group, resulting in the formation of water (H2O) and a negatively charged alkoxide ion (RO⁻). - **Step 2: Intramolecular Substitution** - The negatively charged alkoxide ion (RO⁻) formed in the first step acts as a nucleophile. It attacks the carbon bonded to the bromine atom, leading to the expulsion of the bromide ion (Br⁻) and the formation of a new carbon-oxygen bond. ### Expected Product: The product of this reaction is typically an epoxide (a three-membered ether ring), formed by the intramolecular attack of the alkoxide ion on the carbon atom bearing the leaving group (bromide). The structure of the resulting epoxide involves the oxygens forming a ring with the two adjacent carbons that were part of the initial four-carbon chain. ### Conclusion: The described process transforms the starting material (4-bromo-2-butanol) using sodium hydride in a substitution reaction to produce an epoxide. --- This content outlines a substitution reaction mechanism in organic chemistry, typically covered in undergraduate-level courses. It includes a thorough explanation of the chemical processes involved, making it suitable for students seeking to understand the reaction pathway and the product formation.
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