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Explain the difference in the products for the compounds below. Using chair structures may help. Is this an E1, E2, S№1 or SN2 reaction? KOtBu A B CI ||||||| CI DMSO KOtBu DMSO

Explain the difference in the products for the compounds below. Using chair structures may help. Is this an E1, E2, S№1 or SN2 reaction? KOtBu A B CI ||||||| CI DMSO KOtBu 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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**Question 23:** Explain the difference in the products for the compounds below. Using chair structures may help. Is this an E1, E2, S<sub>N</sub>1, or S<sub>N</sub>2 reaction? **Compounds:** - Structure A: - A cyclohexane ring with a chlorine atom attached to one carbon, with a wedge indicating an axial position. - Reaction Conditions: - Reactant: KOTBu - Solvent: DMSO - Product for Structure A: - A cyclohexane ring with a double bond, indicating an elimination reaction product. - Structure B: - A cyclohexane ring with a chlorine atom attached to one carbon, with a dash indicating an equatorial position. - Reaction Conditions: - Reactant: KOTBu - Solvent: DMSO - Product for Structure B: - A cyclohexane ring with a double bond, indicating an elimination reaction product. **Explanation:** This problem involves analyzing the elimination reactions of compounds A and B under the influence of potassium tert-butoxide (KOTBu) in DMSO. The difference in the products is due to the stereochemistry of the chlorine substituent (axial for A and equatorial for B), which affects the E2 reaction mechanism. E2 reactions require the leaving group and a hydrogen atom on the adjacent carbon to be anti-coplanar. - Compound A has the chlorine atom in the axial position, aligning well for anti-coplanar elimination to form a double bond. - Compound B has the chlorine atom in the equatorial position, making the formation of the product through an E2 mechanism less favorable or requiring a chair flip to reach axial orientation. Overall, this exercise highlights the impact of stereochemistry on reaction mechanisms and outcomes, specifically how the orientation of substituents in cyclic compounds can influence the pathway (E2 in this case) and thus the final products formed.
Transcribed Image Text:**Question 23:** Explain the difference in the products for the compounds below. Using chair structures may help. Is this an E1, E2, S<sub>N</sub>1, or S<sub>N</sub>2 reaction? **Compounds:** - Structure A: - A cyclohexane ring with a chlorine atom attached to one carbon, with a wedge indicating an axial position. - Reaction Conditions: - Reactant: KOTBu - Solvent: DMSO - Product for Structure A: - A cyclohexane ring with a double bond, indicating an elimination reaction product. - Structure B: - A cyclohexane ring with a chlorine atom attached to one carbon, with a dash indicating an equatorial position. - Reaction Conditions: - Reactant: KOTBu - Solvent: DMSO - Product for Structure B: - A cyclohexane ring with a double bond, indicating an elimination reaction product. **Explanation:** This problem involves analyzing the elimination reactions of compounds A and B under the influence of potassium tert-butoxide (KOTBu) in DMSO. The difference in the products is due to the stereochemistry of the chlorine substituent (axial for A and equatorial for B), which affects the E2 reaction mechanism. E2 reactions require the leaving group and a hydrogen atom on the adjacent carbon to be anti-coplanar. - Compound A has the chlorine atom in the axial position, aligning well for anti-coplanar elimination to form a double bond. - Compound B has the chlorine atom in the equatorial position, making the formation of the product through an E2 mechanism less favorable or requiring a chair flip to reach axial orientation. Overall, this exercise highlights the impact of stereochemistry on reaction mechanisms and outcomes, specifically how the orientation of substituents in cyclic compounds can influence the pathway (E2 in this case) and thus the final products formed.
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