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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![**Nucleophilic Substitution Reaction Mechanism**
**Question:**
Which mechanism is this reaction most likely to use?
**Reaction Details:**
1. **Starting Material:** Cyclohexyl bromide (a six-membered cyclohexane ring with a bromine atom attached).
2. **Reactant:** NaSH (sodium hydrosulfide).
3. **Product:** Cyclohexyl mercaptan (a six-membered cyclohexane ring with a thiol group, SH, attached).
The reaction scheme is as follows:
\[ \text{Cyclohexyl bromide (Br) + NaSH} \rightarrow \text{Cyclohexyl mercaptan (SH)} \]
**Reaction Mechanism Options:**
- \( S_N1 \)
- \( S_N2 \)
**Explanation:**
The diagram likely indicates a nucleophilic substitution reaction where the bromine atom is replaced by the thiol group. The mechanism could proceed via either an \( S_N1 \) or \( S_N2 \) pathway. Students should analyze the substrate structure, the nature of the leaving group, and the nucleophile to determine the most probable mechanism.
In this case, cyclohexyl bromide is a primary alkyl halide, NaSH is a strong nucleophile, and the reaction is likely to proceed via an \( S_N2 \) mechanism due to the direct substitution of the bromine atom by the thiol group, typical for primary substrates with strong nucleophiles.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F61e08100-95fd-4f62-9899-841872b9b376%2F6322f072-ab96-49de-8739-e2cc2b10754e%2Fplj4l3j_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Nucleophilic Substitution Reaction Mechanism**
**Question:**
Which mechanism is this reaction most likely to use?
**Reaction Details:**
1. **Starting Material:** Cyclohexyl bromide (a six-membered cyclohexane ring with a bromine atom attached).
2. **Reactant:** NaSH (sodium hydrosulfide).
3. **Product:** Cyclohexyl mercaptan (a six-membered cyclohexane ring with a thiol group, SH, attached).
The reaction scheme is as follows:
\[ \text{Cyclohexyl bromide (Br) + NaSH} \rightarrow \text{Cyclohexyl mercaptan (SH)} \]
**Reaction Mechanism Options:**
- \( S_N1 \)
- \( S_N2 \)
**Explanation:**
The diagram likely indicates a nucleophilic substitution reaction where the bromine atom is replaced by the thiol group. The mechanism could proceed via either an \( S_N1 \) or \( S_N2 \) pathway. Students should analyze the substrate structure, the nature of the leaving group, and the nucleophile to determine the most probable mechanism.
In this case, cyclohexyl bromide is a primary alkyl halide, NaSH is a strong nucleophile, and the reaction is likely to proceed via an \( S_N2 \) mechanism due to the direct substitution of the bromine atom by the thiol group, typical for primary substrates with strong nucleophiles.
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