Consider the reaction sequence below to answer the following questions: Hg(OAc)2, H₂O/THE لی ستی OH HgOAc + HOẠc NaBH ОН + Hg Write the complete reaction mechanism for the first step of this reaction sequence. Show all electron flow with arrows and show all intermediate structures.
Consider the reaction sequence below to answer the following questions: Hg(OAc)2, H₂O/THE لی ستی OH HgOAc + HOẠc NaBH ОН + Hg Write the complete reaction mechanism for the first step of this reaction sequence. Show all electron flow with arrows and show all intermediate structures.
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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
Transcribed Image Text:**Title: Reaction Mechanism and Sequence Analysis**
**Instructions:**
1. **Consider the reaction sequence below to answer the following questions:**
The sequence starts with a benzene ring with an attached vinyl group (styrene). The reaction involves the following key steps and reagents:
- Reaction with \( \text{Hg(OAc)}_2, \text{H}_2\text{O/THF} \) resulting in the formation of a phenylmercuric acetate derivative.
- Subsequent reduction with \( \text{NaBH}_4 \) yielding an alcohol product.
2. **Reaction Details:**
- **Step 1: Oxymercuration-Demercuration**
The vinyl compound reacts with \( \text{Hg(OAc)}_2 \) in the presence of water and tetrahydrofuran (THF). This step adds the acetate group and hydroxyl group to the double bond, forming an intermediate that includes a hydroxyl group (OH) and an acetate group (HgOAc).
- **Intermediate Formation:**
The intermediate has a phenyl group with an attached carbon chain bearing both an OH and HgOAc group.
- **Step 2: Reduction**
Treatment with \( \text{NaBH}_4 \) reduces the intermediate, removing the mercury group and forming the final alcohol product.
- **Final Product:**
The final product is an alcohol with the hydroxyl group (OH) attached to the former vinyl carbon, ensuring Markovnikov orientation.
3. **Write the complete reaction mechanism for the first step of this reaction sequence. Show all electron flow with arrows and display all intermediate structures.**
Diagrammatic representation should include:
- Arrow pushing to show electron flow during the formation of the mercurinium ion intermediate.
- Arrows indicating the opening of the mercurinium ion and subsequent attack by water, leading to the intermediate formation.
**Conclusion:**
This sequence provides a clear example of the oxymercuration-demercuration reaction, which is an important method for synthesizing alcohols from alkenes. Ensure to analyze the mechanistic details, highlighting the importance of each reagent and the electron flow involved in transforming starting materials to the final product.
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