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
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.
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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