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Draw the major elimination and substitution products formed in this reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers, where applicable. Ignore any inorganic byproducts. CH3CH2ONA, CH3CH2OH heat CI

Draw the major elimination and substitution products formed in this reaction. Use a dash or wedge bond to indicate stereochemistry of substituents on asymmetric centers, where applicable. Ignore any inorganic byproducts. CH3CH2ONA, CH3CH2OH heat CI

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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**Reaction Mechanism Overview:** This exercise asks us to identify the major elimination and substitution products for a given reaction. The reaction is to use a dash or wedge bond to indicate stereochemistry on asymmetric centers, ignoring inorganic byproducts. **Reaction Setup:** - **Reactant:** A chlorocyclohexane compound. - **Reagents:** Sodium ethoxide (CH₃CH₂ONa) in ethanol (CH₃CH₂OH). - **Conditions:** Heat is applied. **Explanation of Reaction:** - **Elimination Reaction (E2):** The presence of a strong base (sodium ethoxide) and heat suggests an E2 mechanism is likely. This would result in the formation of an alkene. The hydrogen adjacent to the carbon bonded to chlorine will be removed, leading to the formation of a double bond after the removal of Cl⁻. - **Substitution Reaction (Sₙ2):** The nucleophile (ethoxide) can replace the leaving group (chloride), resulting in an ether product if this pathway is favored. **Stereochemistry Consideration:** Use of dash/wedge bonds is essential to show the three-dimensional arrangement of atoms around the asymmetric centers created after the reaction. This setup provides a practical means to understand reaction mechanisms, highlighting competition between elimination and substitution processes.
Transcribed Image Text:**Reaction Mechanism Overview:** This exercise asks us to identify the major elimination and substitution products for a given reaction. The reaction is to use a dash or wedge bond to indicate stereochemistry on asymmetric centers, ignoring inorganic byproducts. **Reaction Setup:** - **Reactant:** A chlorocyclohexane compound. - **Reagents:** Sodium ethoxide (CH₃CH₂ONa) in ethanol (CH₃CH₂OH). - **Conditions:** Heat is applied. **Explanation of Reaction:** - **Elimination Reaction (E2):** The presence of a strong base (sodium ethoxide) and heat suggests an E2 mechanism is likely. This would result in the formation of an alkene. The hydrogen adjacent to the carbon bonded to chlorine will be removed, leading to the formation of a double bond after the removal of Cl⁻. - **Substitution Reaction (Sₙ2):** The nucleophile (ethoxide) can replace the leaving group (chloride), resulting in an ether product if this pathway is favored. **Stereochemistry Consideration:** Use of dash/wedge bonds is essential to show the three-dimensional arrangement of atoms around the asymmetric centers created after the reaction. This setup provides a practical means to understand reaction mechanisms, highlighting competition between elimination and substitution processes.
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