Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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### 4a. Challenge Problem: Where will that come from?

Your new boss at Albion Malleable Chemical Company just told you to make the product below. She told you to use one of the bromothiols below, you just can’t remember which one she said. Using your outstanding Albion College education, and knowing that sulfur acts like oxygen, figure out which one will work, and which one won’t, and explain it here with text, mechanisms, complete sentences, and logic.

### Problem Description:
You are provided with two bromothiols:
1. Structure 1:
   - Bromine (Br) attached to a cyclohexane ring with an -SH group (thiol).

2. Structure 2:
   - Bromine (Br) attached to a cyclohexane ring with an -SH group (thiol) on different positions.

### Reaction Information:
- Reactant: One of the bromothiols.
- Reagent: NaH (Sodium Hydride).
- Product: A bridged bicyclic sulfide.

### Analysis:
1. **Identify the correct bromothiol to use**:
   - The product is a bicyclic ring containing sulfur. 
   - Consider the role of sulfur in the mechanism and how it mimics oxygen in terms of nucleophilicity and ability to form rings.

2. **Mechanism**:
   - When reacting with NaH, sulfur (in the thiol as -SH) acts as a nucleophile.
   - NaH deprotonates the thiol (-SH) to form a thiolate anion (S-).
   - The formed thiolate anion then attacks the carbon bonded to the bromine (Br), leading to a nucleophilic substitution reaction (likely SN2).
   - The sulfur then forms a ring by attacking the other electrophilic carbon, forming the bicyclic structure.

3. **Selecting the Correct Bromothiol**:
   - For the product to form the specific bicyclic structure, the initial positions of the -SH and Br groups in the reactant are crucial.
   - Only one specific positioning of Br and -SH in the bromothiol will allow for the correct cyclization and formation of the target bicyclic sulfide product.

### Conclusion:
- Analyze both bromothiols for the ability to form the bicyclic ring:
  - Structure 1 or Structure 2.
- The correct reactant will have a positioning
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Transcribed Image Text:### 4a. Challenge Problem: Where will that come from? Your new boss at Albion Malleable Chemical Company just told you to make the product below. She told you to use one of the bromothiols below, you just can’t remember which one she said. Using your outstanding Albion College education, and knowing that sulfur acts like oxygen, figure out which one will work, and which one won’t, and explain it here with text, mechanisms, complete sentences, and logic. ### Problem Description: You are provided with two bromothiols: 1. Structure 1: - Bromine (Br) attached to a cyclohexane ring with an -SH group (thiol). 2. Structure 2: - Bromine (Br) attached to a cyclohexane ring with an -SH group (thiol) on different positions. ### Reaction Information: - Reactant: One of the bromothiols. - Reagent: NaH (Sodium Hydride). - Product: A bridged bicyclic sulfide. ### Analysis: 1. **Identify the correct bromothiol to use**: - The product is a bicyclic ring containing sulfur. - Consider the role of sulfur in the mechanism and how it mimics oxygen in terms of nucleophilicity and ability to form rings. 2. **Mechanism**: - When reacting with NaH, sulfur (in the thiol as -SH) acts as a nucleophile. - NaH deprotonates the thiol (-SH) to form a thiolate anion (S-). - The formed thiolate anion then attacks the carbon bonded to the bromine (Br), leading to a nucleophilic substitution reaction (likely SN2). - The sulfur then forms a ring by attacking the other electrophilic carbon, forming the bicyclic structure. 3. **Selecting the Correct Bromothiol**: - For the product to form the specific bicyclic structure, the initial positions of the -SH and Br groups in the reactant are crucial. - Only one specific positioning of Br and -SH in the bromothiol will allow for the correct cyclization and formation of the target bicyclic sulfide product. ### Conclusion: - Analyze both bromothiols for the ability to form the bicyclic ring: - Structure 1 or Structure 2. - The correct reactant will have a positioning
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