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Which product(s) would form under the conditions given below? Ph он HO Ph HO Ph но, он 1. MCPBA Ph OH HO Ph Ph OH Ph Ph 2. H30* B D ОА В D O A and B O B and C O C and D O All of the products will form under the conditions given. O O O O

Which product(s) would form under the conditions given below? Ph он HO Ph HO Ph но, он 1. MCPBA Ph OH HO Ph Ph OH Ph Ph 2. H30* B D ОА В D O A and B O B and C O C and D O All of the products will form under the conditions given. O O O O

Chemistry
Chemistry
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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
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**Question:** Which product(s) would form under the conditions given below? **Reaction:** A reaction scheme is presented where the starting material is a styrene derivative. The reaction involves two steps: 1. MCPBA (meta-Chloroperoxybenzoic acid) 2. \( \text{H}_3\text{O}^+ \) (hydronium ion) **Possible Products:** - **A:** A vicinal diol with two hydroxyl groups oriented in a syn configuration relative to the phenyl groups. - **B:** A vicinal diol with one hydroxyl group oriented syn and the other anti to the phenyl groups. - **C:** Another vicinal diol with one hydroxyl group oriented syn and the other anti to the phenyl groups. - **D:** A vicinal diol with both hydroxyl groups oriented in an anti configuration relative to the phenyl groups. **Options:** - \( \circ \) A - \( \circ \) B - \( \circ \) C - \( \circ \) D - \( \circ \) A and B - \( \circ \) B and C - \( \circ \) C and D - \( \circ \) All of the products will form under the conditions given. **Diagram Explanation:** The diagram represents the reaction of a substituted alkene with MCPBA, which typically forms an epoxide. The epoxide is then opened to form vicinal diols in the presence of \( \text{H}_3\text{O}^+ \), potentially resulting in different stereochemical outcomes (syn or anti diols). The question asks which of these diols would be expected as products.
Transcribed Image Text:**Question:** Which product(s) would form under the conditions given below? **Reaction:** A reaction scheme is presented where the starting material is a styrene derivative. The reaction involves two steps: 1. MCPBA (meta-Chloroperoxybenzoic acid) 2. \( \text{H}_3\text{O}^+ \) (hydronium ion) **Possible Products:** - **A:** A vicinal diol with two hydroxyl groups oriented in a syn configuration relative to the phenyl groups. - **B:** A vicinal diol with one hydroxyl group oriented syn and the other anti to the phenyl groups. - **C:** Another vicinal diol with one hydroxyl group oriented syn and the other anti to the phenyl groups. - **D:** A vicinal diol with both hydroxyl groups oriented in an anti configuration relative to the phenyl groups. **Options:** - \( \circ \) A - \( \circ \) B - \( \circ \) C - \( \circ \) D - \( \circ \) A and B - \( \circ \) B and C - \( \circ \) C and D - \( \circ \) All of the products will form under the conditions given. **Diagram Explanation:** The diagram represents the reaction of a substituted alkene with MCPBA, which typically forms an epoxide. The epoxide is then opened to form vicinal diols in the presence of \( \text{H}_3\text{O}^+ \), potentially resulting in different stereochemical outcomes (syn or anti diols). The question asks which of these diols would be expected as products.
**Organic Chemistry Reaction Analysis** **Objective:** Determine the major organic product formed under the specific reaction conditions. **Reaction Conditions:** 1. Reagents: - Mercuric acetate \((\text{Hg(OAc)}_2)\) and water \((\text{H}_2\text{O})\) - Sodium borohydride \((\text{NaBH}_4)\) 2. Reaction Pathway: - Initial Addition: The reaction starts with the addition of mercuric acetate in water, indicating an oxymercuration-demercuration reaction. - Reduction: Sodium borohydride is used to reduce the intermediate. **Starting Material:** - Cyclopentene (a five-membered ring with a double bond) **Options for Major Product:** 1. Acetoxycyclopentane (single bond with an acetoxy group attached) 2. Cyclopentanol (single bond with a hydroxyl group attached) 3. Cyclopentylmethanol (attached hydroxyl group in a side chain) 4. 1,2-Cyclopentanediol (two hydroxyl groups on adjacent carbons) 5. Cyclopentylborane (attached borane group) **Analysis:** - The oxymercuration-demercuration reaction typically results in the addition of a hydroxyl group \((-OH)\) across the double bond without rearrangement, favoring Markovnikov addition (hydroxyl group on the more substituted carbon). **Expected Major Product:** - Cyclopentanol, represented as a cyclopentane with a hydroxyl group, is the expected product following these reaction conditions. Use this reaction mechanism and product identification to understand the process of oxymercuration-demercuration in organic synthesis.
Transcribed Image Text:**Organic Chemistry Reaction Analysis** **Objective:** Determine the major organic product formed under the specific reaction conditions. **Reaction Conditions:** 1. Reagents: - Mercuric acetate \((\text{Hg(OAc)}_2)\) and water \((\text{H}_2\text{O})\) - Sodium borohydride \((\text{NaBH}_4)\) 2. Reaction Pathway: - Initial Addition: The reaction starts with the addition of mercuric acetate in water, indicating an oxymercuration-demercuration reaction. - Reduction: Sodium borohydride is used to reduce the intermediate. **Starting Material:** - Cyclopentene (a five-membered ring with a double bond) **Options for Major Product:** 1. Acetoxycyclopentane (single bond with an acetoxy group attached) 2. Cyclopentanol (single bond with a hydroxyl group attached) 3. Cyclopentylmethanol (attached hydroxyl group in a side chain) 4. 1,2-Cyclopentanediol (two hydroxyl groups on adjacent carbons) 5. Cyclopentylborane (attached borane group) **Analysis:** - The oxymercuration-demercuration reaction typically results in the addition of a hydroxyl group \((-OH)\) across the double bond without rearrangement, favoring Markovnikov addition (hydroxyl group on the more substituted carbon). **Expected Major Product:** - Cyclopentanol, represented as a cyclopentane with a hydroxyl group, is the expected product following these reaction conditions. Use this reaction mechanism and product identification to understand the process of oxymercuration-demercuration in organic synthesis.
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