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3. In the E2 reaction of 1-bromo-4-tert-butylcyclohexane, the cis isomer reacts 500 times faster than the trans isomer. Provide an explanation for why this is. Br fast cis Br slow trans

3. In the E2 reaction of 1-bromo-4-tert-butylcyclohexane, the cis isomer reacts 500 times faster than the trans isomer. Provide an explanation for why this is. Br fast cis Br slow trans

Chemistry
Chemistry
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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
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3. In the E2 reaction of 1-bromo-4-tert-butylcyclohexane, the cis isomer reacts 500 times faster than the trans isomer. Provide an explanation for why this is. **Diagrams:** 1. **Cis Isomer Reaction:** - **Reactant:** The cis isomer of 1-bromo-4-tert-butylcyclohexane is depicted. The bromine atom (Br) and the tert-butyl group are on the same side of the cyclohexane ring. - **Reaction Arrow:** Indicates a fast E2 reaction characterized by the removal of the leaving group (Br) and the formation of a double bond. - **Product:** The resulting alkene product shows a double bond formed within the cyclohexane ring. 2. **Trans Isomer Reaction:** - **Reactant:** The trans isomer is shown with the bromine atom and tert-butyl group on opposite sides of the cyclohexane ring. - **Reaction Arrow:** Indicates a slow E2 reaction. - **Product:** Similar alkene product but with a slower reaction rate compared to the cis isomer. **Explanation:** The difference in reaction rates can be attributed to the stereochemistry of the isomers. In the cis isomer, the leaving group and the hydrogen atom that is removed during the E2 reaction are already oriented in such a way that the reaction can occur more efficiently. This is due to the favorable antiperiplanar arrangement, which is optimal for the E2 mechanism. In contrast, the trans isomer requires additional rotation to achieve this arrangement, slowing down the reaction.
Transcribed Image Text:3. In the E2 reaction of 1-bromo-4-tert-butylcyclohexane, the cis isomer reacts 500 times faster than the trans isomer. Provide an explanation for why this is. **Diagrams:** 1. **Cis Isomer Reaction:** - **Reactant:** The cis isomer of 1-bromo-4-tert-butylcyclohexane is depicted. The bromine atom (Br) and the tert-butyl group are on the same side of the cyclohexane ring. - **Reaction Arrow:** Indicates a fast E2 reaction characterized by the removal of the leaving group (Br) and the formation of a double bond. - **Product:** The resulting alkene product shows a double bond formed within the cyclohexane ring. 2. **Trans Isomer Reaction:** - **Reactant:** The trans isomer is shown with the bromine atom and tert-butyl group on opposite sides of the cyclohexane ring. - **Reaction Arrow:** Indicates a slow E2 reaction. - **Product:** Similar alkene product but with a slower reaction rate compared to the cis isomer. **Explanation:** The difference in reaction rates can be attributed to the stereochemistry of the isomers. In the cis isomer, the leaving group and the hydrogen atom that is removed during the E2 reaction are already oriented in such a way that the reaction can occur more efficiently. This is due to the favorable antiperiplanar arrangement, which is optimal for the E2 mechanism. In contrast, the trans isomer requires additional rotation to achieve this arrangement, slowing down the reaction.
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