Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question
**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.
expand button
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.
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY