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Predict all product (s) of the following reactic applies. Determine which one is the major product: tomo DMF O Na DMSO

Predict all product (s) of the following reactic applies. Determine which one is the major product: tomo DMF O Na DMSO

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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### Organic Chemistry Reactions and Stereochemistry #### Reaction Prediction and Stereochemical Outcomes **Objective:** Predict all product(s) of the following reactions and show the stereochemical outcome if applicable. Determine which one is the major product. --- **Reaction 1:** - **Reactants:** - A cyclohexane ring with a chlorine (Cl) substituent in an axial position. - The nucleophile is sodium tert-butoxide (tert-butyl group with a negatively charged oxygen and a sodium cation), dissolved in DMF (Dimethylformamide). - **Reaction Scheme:** ``` Cl ———————> | * | + tBuO−Na+ DMF ``` **Explanation:** In this reaction, the base (tert-butoxide) will deprotonate the cyclohexane ring, leading to the elimination of the chlorine substituent and formation of a double bond (alkene). Due to the strong basic nature of tert-butoxide, the reaction follows an E2 mechanism, which favors the formation of the most stable (more substituted) alkene through an anti-elimination process. --- **Reaction 2:** - **Reactants:** - A cyclohexane ring with a chlorine (Cl) substituent in an axial position, adjacent to a methyl group. - The nucleophile is sodium ethoxide (an ethyl group with a negatively charged oxygen and a sodium cation), dissolved in DMSO (Dimethyl sulfoxide). - **Reaction Scheme:** ``` Cl ———————> | * | Me − + EtO−Na+ DMSO ``` **Explanation:** This reaction involves sodium ethoxide, a strong base, facilitating an E2 elimination reaction. Similar to Reaction 1, the base abstracts a proton leading to the elimination of chlorine, and the formation of a double bond in the cyclohexane ring resulting in the most stable alkene. Given the substituent adjacent to the reaction site, the stereochemical outcome will be considered, ensuring anti-periplanar geometry for the elimination process. #### Determining the Major Product: In both reactions, we aim to form the most substituted and hence, the most stable alkene due to Zaitsev's rule (which states the more substituted alkene is the
Transcribed Image Text:### Organic Chemistry Reactions and Stereochemistry #### Reaction Prediction and Stereochemical Outcomes **Objective:** Predict all product(s) of the following reactions and show the stereochemical outcome if applicable. Determine which one is the major product. --- **Reaction 1:** - **Reactants:** - A cyclohexane ring with a chlorine (Cl) substituent in an axial position. - The nucleophile is sodium tert-butoxide (tert-butyl group with a negatively charged oxygen and a sodium cation), dissolved in DMF (Dimethylformamide). - **Reaction Scheme:** ``` Cl ———————> | * | + tBuO−Na+ DMF ``` **Explanation:** In this reaction, the base (tert-butoxide) will deprotonate the cyclohexane ring, leading to the elimination of the chlorine substituent and formation of a double bond (alkene). Due to the strong basic nature of tert-butoxide, the reaction follows an E2 mechanism, which favors the formation of the most stable (more substituted) alkene through an anti-elimination process. --- **Reaction 2:** - **Reactants:** - A cyclohexane ring with a chlorine (Cl) substituent in an axial position, adjacent to a methyl group. - The nucleophile is sodium ethoxide (an ethyl group with a negatively charged oxygen and a sodium cation), dissolved in DMSO (Dimethyl sulfoxide). - **Reaction Scheme:** ``` Cl ———————> | * | Me − + EtO−Na+ DMSO ``` **Explanation:** This reaction involves sodium ethoxide, a strong base, facilitating an E2 elimination reaction. Similar to Reaction 1, the base abstracts a proton leading to the elimination of chlorine, and the formation of a double bond in the cyclohexane ring resulting in the most stable alkene. Given the substituent adjacent to the reaction site, the stereochemical outcome will be considered, ensuring anti-periplanar geometry for the elimination process. #### Determining the Major Product: In both reactions, we aim to form the most substituted and hence, the most stable alkene due to Zaitsev's rule (which states the more substituted alkene is the
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