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1. Hg(OAc)2, H,O 2. NaBH4 1. Hg(OAc), H,о 2. NaBH4 1. Hg(OAc)2, H,O 2. NaBH4

1. Hg(OAc)2, H,O 2. NaBH4 1. Hg(OAc), H,о 2. NaBH4 1. Hg(OAc)2, H,O 2. NaBH4

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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### Practice Problems: Oxymercuration-Demercuration Reactions These practice problems involve the oxymercuration-demercuration reaction sequence. This method is used to convert alkenes into alcohols. The general reaction involves two main steps, each with specific reagents, as outlined below: #### Problem 1: - **Starting Material:** An alkene with a branched structure. - **Reagents:** 1. **Hg(OAc)₂, H₂O:** This is the oxymercuration step, where the mercuric acetate and water react with the alkene. 2. **NaBH₄:** This is the demercuration step, where sodium borohydride reduces the intermediate, transforming it into an alcohol. #### Problem 2: - **Starting Material:** Another branched alkene with a different structure than Problem 1. - **Reagents:** (same as Problem 1) 1. **Hg(OAc)₂, H₂O** 2. **NaBH₄** #### Problem 3: - **Starting Material:** A cycloalkene. - **Reagents:** (same as above) 1. **Hg(OAc)₂, H₂O** 2. **NaBH₄** ### Explanation: - **Oxymercuration**: In this step, the alkene reacts with mercuric acetate in water. A mercurinium ion intermediate is formed, which then reacts with water to give an organomercury compound. - **Demercuration**: In the second step, sodium borohydride (NaBH₄) reduces the organomercury intermediate to form an alcohol. This step removes the mercury group. These problems offer practice for predicting the product of the reaction sequence and understanding the regioselectivity involved, as the alcohol typically forms at the more substituted carbon in accordance with Markovnikov's rule.
Transcribed Image Text:### Practice Problems: Oxymercuration-Demercuration Reactions These practice problems involve the oxymercuration-demercuration reaction sequence. This method is used to convert alkenes into alcohols. The general reaction involves two main steps, each with specific reagents, as outlined below: #### Problem 1: - **Starting Material:** An alkene with a branched structure. - **Reagents:** 1. **Hg(OAc)₂, H₂O:** This is the oxymercuration step, where the mercuric acetate and water react with the alkene. 2. **NaBH₄:** This is the demercuration step, where sodium borohydride reduces the intermediate, transforming it into an alcohol. #### Problem 2: - **Starting Material:** Another branched alkene with a different structure than Problem 1. - **Reagents:** (same as Problem 1) 1. **Hg(OAc)₂, H₂O** 2. **NaBH₄** #### Problem 3: - **Starting Material:** A cycloalkene. - **Reagents:** (same as above) 1. **Hg(OAc)₂, H₂O** 2. **NaBH₄** ### Explanation: - **Oxymercuration**: In this step, the alkene reacts with mercuric acetate in water. A mercurinium ion intermediate is formed, which then reacts with water to give an organomercury compound. - **Demercuration**: In the second step, sodium borohydride (NaBH₄) reduces the organomercury intermediate to form an alcohol. This step removes the mercury group. These problems offer practice for predicting the product of the reaction sequence and understanding the regioselectivity involved, as the alcohol typically forms at the more substituted carbon in accordance with Markovnikov's rule.
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