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a) what is b) what c) How wrong Br would could with the the кот ви make reaction the product in as written Ò below? veaction correct? part a) form?

a) what is b) what c) How wrong Br would could with the the кот ви make reaction the product in as written Ò below? veaction correct? part a) form?

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 3 ### a) What is wrong with the reaction as written below? The image shows a cyclic compound with a bromine (Br) substituent, which is drawn as a wedge, indicating it is above the plane of the cyclohexane ring. This compound is reacted with potassium tert-butoxide (KOtBu) to form a cyclohexene. The issue is that the elimination reaction requires an anti-periplanar arrangement, typically resulting in the formation of a double bond where the leaving group (Br) and the hydrogen to be removed are trans to each other, which is not possible with the current stereochemistry. ### b) What would make the reaction correct? For the reaction to proceed correctly, an anti-periplanar (trans) arrangement between the bromine and a hydrogen atom on an adjacent carbon is necessary. This often requires a ring flip to achieve the trans-diaxial conformation. ### c) How could the product in part a) form? The formation of the product can occur via an elimination reaction where the hydrogen and the bromine are anti-periplanar, allowing for the correct overlap of orbitals to facilitate the leaving group's departure and the formation of the double bond. This might require geometric adjustments in the substrate to reach the reactive conformation.
Transcribed Image Text:## Question 3 ### a) What is wrong with the reaction as written below? The image shows a cyclic compound with a bromine (Br) substituent, which is drawn as a wedge, indicating it is above the plane of the cyclohexane ring. This compound is reacted with potassium tert-butoxide (KOtBu) to form a cyclohexene. The issue is that the elimination reaction requires an anti-periplanar arrangement, typically resulting in the formation of a double bond where the leaving group (Br) and the hydrogen to be removed are trans to each other, which is not possible with the current stereochemistry. ### b) What would make the reaction correct? For the reaction to proceed correctly, an anti-periplanar (trans) arrangement between the bromine and a hydrogen atom on an adjacent carbon is necessary. This often requires a ring flip to achieve the trans-diaxial conformation. ### c) How could the product in part a) form? The formation of the product can occur via an elimination reaction where the hydrogen and the bromine are anti-periplanar, allowing for the correct overlap of orbitals to facilitate the leaving group's departure and the formation of the double bond. This might require geometric adjustments in the substrate to reach the reactive conformation.
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