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.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F61a43bfd-18b5-4406-a2b4-a4c6180dbd9a%2Ff28d6d00-96e9-4d1d-9695-8535d9be9f35%2Fdwskwmm_processed.png&w=3840&q=75)
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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