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10.69 Draw a stepwise mechanism for the following reaction. ay OH H₂SO4 os + H₂O

10.69 Draw a stepwise mechanism for the following reaction. ay OH H₂SO4 os + H₂O

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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**Stepwise Mechanism for Organic Reaction** In this exercise, you are required to draw a stepwise mechanism for an organic reaction involving the dehydration of an alcohol using sulfuric acid (\( \text{H}_2\text{SO}_4 \)) as a catalyst. **Reaction Overview:** - **Starting Material:** A cyclopentene ring attached to a chain with an alcohol group (\( \text{OH} \)) and a dimethyl group. - **Reagents Used:** \( \text{H}_2\text{SO}_4 \) (Sulfuric Acid) - **Products Formed:** - A bicyclic compound with two alkene groups is formed. - Water (\( \text{H}_2\text{O} \)) is also produced as a byproduct. **Mechanism Explanation:** 1. **Protonation of Alcohol Group:** - The reaction begins with the protonation of the hydroxyl group using sulfuric acid. This step makes the hydroxyl group a better leaving group. 2. **Formation of a Carbocation:** - After protonation, the water molecule leaves, forming a carbocation. 3. **Rearrangement:** - The carbocation may rearrange to a more stable carbocation if necessary, potentially involving shifts or ring expansions. 4. **Cyclization:** - The intermediate undergoes cyclization through intramolecular attack, resulting in the formation of a double bond. 5. **Elimination:** - The final step involves the removal of a proton to form the desired bicyclic compound with a double bond. 6. **Removal of Water:** - The reaction also results in the formation of water as a byproduct. This mechanism illustrates the common organic chemistry theme of elimination reactions where alcohols are converted to alkenes, often using acid catalysis. Understanding each step allows for insight into bond formation and reorganization during organic transformations.
Transcribed Image Text:**Stepwise Mechanism for Organic Reaction** In this exercise, you are required to draw a stepwise mechanism for an organic reaction involving the dehydration of an alcohol using sulfuric acid (\( \text{H}_2\text{SO}_4 \)) as a catalyst. **Reaction Overview:** - **Starting Material:** A cyclopentene ring attached to a chain with an alcohol group (\( \text{OH} \)) and a dimethyl group. - **Reagents Used:** \( \text{H}_2\text{SO}_4 \) (Sulfuric Acid) - **Products Formed:** - A bicyclic compound with two alkene groups is formed. - Water (\( \text{H}_2\text{O} \)) is also produced as a byproduct. **Mechanism Explanation:** 1. **Protonation of Alcohol Group:** - The reaction begins with the protonation of the hydroxyl group using sulfuric acid. This step makes the hydroxyl group a better leaving group. 2. **Formation of a Carbocation:** - After protonation, the water molecule leaves, forming a carbocation. 3. **Rearrangement:** - The carbocation may rearrange to a more stable carbocation if necessary, potentially involving shifts or ring expansions. 4. **Cyclization:** - The intermediate undergoes cyclization through intramolecular attack, resulting in the formation of a double bond. 5. **Elimination:** - The final step involves the removal of a proton to form the desired bicyclic compound with a double bond. 6. **Removal of Water:** - The reaction also results in the formation of water as a byproduct. This mechanism illustrates the common organic chemistry theme of elimination reactions where alcohols are converted to alkenes, often using acid catalysis. Understanding each step allows for insight into bond formation and reorganization during organic transformations.
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