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hydroxylation followed by (2) direct alkene cleavage with ozone. For this sequence below, . CH3 Draw the structure of A. 1. OsO4, pyridine 2. NaHSO3, H₂O A

hydroxylation followed by (2) direct alkene cleavage with ozone. For this sequence below, . CH3 Draw the structure of A. 1. OsO4, pyridine 2. NaHSO3, H₂O A

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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**Alkene Hydroxylation and Diol Cleavage Sequence** The sequence of (1) alkene hydroxylation followed by (2) diol cleavage is often an excellent alternative to direct alkene cleavage with ozone. For this sequence below, answer the following questions. **Reaction Sequence:** 1. **Reagents Used:** - *Step 1:* OsO₄ (osmium tetroxide), pyridine - *Step 2:* NaHSO₃ (sodium bisulfite), H₂O (water) **Chemical Reaction:** The starting material is a cyclohexene ring with a methyl group attached, indicated by the structure with a single double bond between two of the carbon atoms. - The first step involves the addition of osmium tetroxide and pyridine, which typically results in the formation of a diol by adding hydroxyl groups to the carbons involved in the double bond. - The second step uses sodium bisulfite in the presence of water for cleaving the diol, which typically leads to the formation of ketones or aldehydes. **Product Formation:** - The product shown as compound B is a keto-aldehyde, indicating that the oxidative cleavage of the diol has resulted in the formation of these functional groups. The structure retains the cyclohexane ring with a CH₃ group, and two adjacent carbonyl compounds formed where the original double bond was, with one of them being an aldehyde. **Exercise:** - Draw the structure of compound A, which is the intermediate formed after the alkene hydroxylation but before the diol cleavage step. **Note:** Understanding the transformation from the alkene through hydroxylation to cleavage products is crucial in organic synthesis, offering an alternative to ozonolysis for achieving similar transformations with potential advantages in selectivity and yield.
Transcribed Image Text:**Alkene Hydroxylation and Diol Cleavage Sequence** The sequence of (1) alkene hydroxylation followed by (2) diol cleavage is often an excellent alternative to direct alkene cleavage with ozone. For this sequence below, answer the following questions. **Reaction Sequence:** 1. **Reagents Used:** - *Step 1:* OsO₄ (osmium tetroxide), pyridine - *Step 2:* NaHSO₃ (sodium bisulfite), H₂O (water) **Chemical Reaction:** The starting material is a cyclohexene ring with a methyl group attached, indicated by the structure with a single double bond between two of the carbon atoms. - The first step involves the addition of osmium tetroxide and pyridine, which typically results in the formation of a diol by adding hydroxyl groups to the carbons involved in the double bond. - The second step uses sodium bisulfite in the presence of water for cleaving the diol, which typically leads to the formation of ketones or aldehydes. **Product Formation:** - The product shown as compound B is a keto-aldehyde, indicating that the oxidative cleavage of the diol has resulted in the formation of these functional groups. The structure retains the cyclohexane ring with a CH₃ group, and two adjacent carbonyl compounds formed where the original double bond was, with one of them being an aldehyde. **Exercise:** - Draw the structure of compound A, which is the intermediate formed after the alkene hydroxylation but before the diol cleavage step. **Note:** Understanding the transformation from the alkene through hydroxylation to cleavage products is crucial in organic synthesis, offering an alternative to ozonolysis for achieving similar transformations with potential advantages in selectivity and yield.
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