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Br SH NaSH + NaBr +

Br SH NaSH + NaBr +

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 8:** For the following reactions, assume the concerted process is taking place and draw a mechanism. **Reaction Scheme:** - Reactants: 1. An alkyl bromide (\[\text{R-CH}_2-\text{Br}\]). 2. Sodium hydrosulfide (\[\text{NaSH}\]). - Products: 1. An alkyl thiol (\[\text{R-CH}_2-\text{SH}\]). 2. Sodium bromide (\[\text{NaBr}\]). --- **Explanation:** In this reaction, the sodium ion (\[\text{Na}^+\]) and the bromide ion (\[\text{Br}^-\]) act as spectator ions. The key transformation involves a nucleophilic substitution where the nucleophile (\[\text{SH}^-\]) replaces the leaving group (\[\text{Br}^-\]) in the alkyl bromide. This is typically an \( \text{S}_\text{N}2 \) (bimolecular nucleophilic substitution) mechanism involving a backside attack by the nucleophile, resulting in the inversion of configuration at the carbon center. The final products are the alkyl thiol and sodium bromide.
Transcribed Image Text:**Question 8:** For the following reactions, assume the concerted process is taking place and draw a mechanism. **Reaction Scheme:** - Reactants: 1. An alkyl bromide (\[\text{R-CH}_2-\text{Br}\]). 2. Sodium hydrosulfide (\[\text{NaSH}\]). - Products: 1. An alkyl thiol (\[\text{R-CH}_2-\text{SH}\]). 2. Sodium bromide (\[\text{NaBr}\]). --- **Explanation:** In this reaction, the sodium ion (\[\text{Na}^+\]) and the bromide ion (\[\text{Br}^-\]) act as spectator ions. The key transformation involves a nucleophilic substitution where the nucleophile (\[\text{SH}^-\]) replaces the leaving group (\[\text{Br}^-\]) in the alkyl bromide. This is typically an \( \text{S}_\text{N}2 \) (bimolecular nucleophilic substitution) mechanism involving a backside attack by the nucleophile, resulting in the inversion of configuration at the carbon center. The final products are the alkyl thiol and sodium bromide.
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