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3. Propose a mechanism for the formation of the 4 alkenes shown below from the reaction of 4-methylpentan-2-ol with aqueous sulfuric acid. OH H2SO4 H20 4-methylpentan-2-ol

3. Propose a mechanism for the formation of the 4 alkenes shown below from the reaction of 4-methylpentan-2-ol with aqueous sulfuric acid. OH H2SO4 H20 4-methylpentan-2-ol

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
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**CHM 2070 Lab: Fall 2020** 3. **Objective**: Propose a mechanism for the formation of the four alkenes shown below from the reaction of 4-methylpentan-2-ol with aqueous sulfuric acid. **Reaction Scheme**: - **Starting Material**: 4-methylpentan-2-ol The initial structure is shown as a molecule with an -OH group attached to the second carbon atom in a pentane chain with a methyl group on the fourth carbon. - **Reagents**: H₂SO₄ (sulfuric acid), H₂O (water) - **Products**: Four alkene molecules The products are shown as follows: 1. A double bond between the second and third carbon atoms. 2. A double bond between the first and second carbon atoms. 3. A double bond between the third and fourth carbon atoms. 4. A double bond between the second and first carbon atoms, with a methyl group on the fourth carbon. **Explanation**: The reaction involves the dehydration of an alcohol to form alkenes through an elimination mechanism, typically via E1 or E2 pathways. The presence of sulfuric acid, a strong acid, facilitates the protonation of the hydroxyl group, forming water as a leaving group. Subsequent rearrangement and loss of a proton lead to the formation of the double bond, with multiple possible outcomes due to the adjacent carbon atoms available for proton removal.
Transcribed Image Text:**CHM 2070 Lab: Fall 2020** 3. **Objective**: Propose a mechanism for the formation of the four alkenes shown below from the reaction of 4-methylpentan-2-ol with aqueous sulfuric acid. **Reaction Scheme**: - **Starting Material**: 4-methylpentan-2-ol The initial structure is shown as a molecule with an -OH group attached to the second carbon atom in a pentane chain with a methyl group on the fourth carbon. - **Reagents**: H₂SO₄ (sulfuric acid), H₂O (water) - **Products**: Four alkene molecules The products are shown as follows: 1. A double bond between the second and third carbon atoms. 2. A double bond between the first and second carbon atoms. 3. A double bond between the third and fourth carbon atoms. 4. A double bond between the second and first carbon atoms, with a methyl group on the fourth carbon. **Explanation**: The reaction involves the dehydration of an alcohol to form alkenes through an elimination mechanism, typically via E1 or E2 pathways. The presence of sulfuric acid, a strong acid, facilitates the protonation of the hydroxyl group, forming water as a leaving group. Subsequent rearrangement and loss of a proton lead to the formation of the double bond, with multiple possible outcomes due to the adjacent carbon atoms available for proton removal.
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