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Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation. CH3OH CH2CH3

Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation. CH3OH CH2CH3

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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### Question 7: "Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation." #### Reaction Description: - **Reactant**: A cyclohexane ring with an iodine (I) atom and an ethyl group (CH₂CH₃) attached to adjacent carbon atoms. - **Reagent**: Methanol (CH₃OH). - **Condition**: Heat (indicated by the delta symbol, Δ). #### Explanation: This reaction likely proceeds through a nucleophilic substitution or elimination mechanism, typical for haloalkanes in the presence of an alcohol under heat. A stepwise mechanism could involve the following: 1. **Formation of a Carbocation**: The iodine group is a good leaving group, so it will detach from the carbon, forming a carbocation on the cyclohexane ring. This is an example of an Sₙ1 reaction (unimolecular nucleophilic substitution). 2. **Nucleophilic Attack**: The methanol (CH₃OH) acts as a nucleophile and attacks the carbocation, forming an intermediary oxonium ion. 3. **Deprotonation**: A base present in the solution, possibly another methanol molecule, will remove a proton from the oxonium ion, forming the ether product. This mechanism would result in the substitution of the iodine group with a methoxy (OCH₃) group from the methanol, yielding the final major organic product. If elimination occurs instead, an alkene could be formed through deprotonation adjacent to the carbocation. The major product prediction and mechanism would depend on the conditions and intermediates explored in deeper studies of reaction specifics, such as the solvent effects and temperature influence.
Transcribed Image Text:### Question 7: "Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation." #### Reaction Description: - **Reactant**: A cyclohexane ring with an iodine (I) atom and an ethyl group (CH₂CH₃) attached to adjacent carbon atoms. - **Reagent**: Methanol (CH₃OH). - **Condition**: Heat (indicated by the delta symbol, Δ). #### Explanation: This reaction likely proceeds through a nucleophilic substitution or elimination mechanism, typical for haloalkanes in the presence of an alcohol under heat. A stepwise mechanism could involve the following: 1. **Formation of a Carbocation**: The iodine group is a good leaving group, so it will detach from the carbon, forming a carbocation on the cyclohexane ring. This is an example of an Sₙ1 reaction (unimolecular nucleophilic substitution). 2. **Nucleophilic Attack**: The methanol (CH₃OH) acts as a nucleophile and attacks the carbocation, forming an intermediary oxonium ion. 3. **Deprotonation**: A base present in the solution, possibly another methanol molecule, will remove a proton from the oxonium ion, forming the ether product. This mechanism would result in the substitution of the iodine group with a methoxy (OCH₃) group from the methanol, yielding the final major organic product. If elimination occurs instead, an alkene could be formed through deprotonation adjacent to the carbocation. The major product prediction and mechanism would depend on the conditions and intermediates explored in deeper studies of reaction specifics, such as the solvent effects and temperature influence.
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