Name the product of the reaction between cyclopentene and OsO4 (+ NaHSO3):

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Name the product of the reaction between cyclopentene and OsO4 (+ NaHSO3):

**Title: Identifying the Reaction Product between Cyclopentene and Osmium Tetroxide (OsO₄)**

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**Reaction Overview:**

In this exercise, we are examining the product formed when cyclopentene reacts with osmium tetroxide (OsO₄) in the presence of sodium bisulfite (NaHSO₃).

**Structure of Reactants:**

The given reactant is cyclopentene, represented by the illustrated cyclopentene molecule, which is a five-membered carbon ring containing one double bond.

**Reaction Mechanism:**

When cyclopentene undergoes oxidation by OsO₄, it forms a cyclic osmate ester intermediate. Subsequent hydrolysis in the presence of a reducing agent such as NaHSO₃ leads to the formation of cis-1,2-cyclopentanediol.

**Expected Product:**

The expected product from this reaction is **cis-1,2-cyclopentanediol**, where the diol (a molecule with two hydroxyl groups) is created by syn addition of hydroxyl groups across the double bond of cyclopentene.

**Explanation of the Product:**

- **cis-1,2-cyclopentanediol**: The two hydroxyl groups are added to the same side of the former double bond, retaining the relative stereochemistry.

By understanding this process, students can explore the concepts of syn-dihydroxylation and the use of specific reagents to achieve desired stereochemical outcomes in organic synthesis.
Transcribed Image Text:**Title: Identifying the Reaction Product between Cyclopentene and Osmium Tetroxide (OsO₄)** --- **Reaction Overview:** In this exercise, we are examining the product formed when cyclopentene reacts with osmium tetroxide (OsO₄) in the presence of sodium bisulfite (NaHSO₃). **Structure of Reactants:** The given reactant is cyclopentene, represented by the illustrated cyclopentene molecule, which is a five-membered carbon ring containing one double bond. **Reaction Mechanism:** When cyclopentene undergoes oxidation by OsO₄, it forms a cyclic osmate ester intermediate. Subsequent hydrolysis in the presence of a reducing agent such as NaHSO₃ leads to the formation of cis-1,2-cyclopentanediol. **Expected Product:** The expected product from this reaction is **cis-1,2-cyclopentanediol**, where the diol (a molecule with two hydroxyl groups) is created by syn addition of hydroxyl groups across the double bond of cyclopentene. **Explanation of the Product:** - **cis-1,2-cyclopentanediol**: The two hydroxyl groups are added to the same side of the former double bond, retaining the relative stereochemistry. By understanding this process, students can explore the concepts of syn-dihydroxylation and the use of specific reagents to achieve desired stereochemical outcomes in organic synthesis.
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