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4. Each of the following alkyl bromides gives only one product in via an E2 mechanism. Provide the mechanism and the product for each of the following reaction. Draw Newman projections to determine the E/Z diastereomers. of Br E2 of Br E2

4. Each of the following alkyl bromides gives only one product in via an E2 mechanism. Provide the mechanism and the product for each of the following reaction. Draw Newman projections to determine the E/Z diastereomers. of Br E2 of Br E2

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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
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**4. Each of the following alkyl bromides gives only one product via an E2 mechanism. Provide the mechanism and the product for each of the following reactions. Draw Newman projections to determine the E/Z diastereomers.** **Description of Diagrams:** The image contains two chemical structures, each related to an E2 elimination reaction involving alkyl bromides. 1. **First Reaction:** - **Structure:** A bromine atom (Br) is attached to a benzene ring (cyclohexane) linked to a carbon chain. The carbon adjacent to the bromine displays a solid wedge, indicating the bromine is coming out of the plane. The hydrogen (not shown) would ideally be anti-periplanar for the E2 reaction to occur efficiently. - **Mechanism:** The E2 mechanism requires the elimination of the bromine atom and the beta hydrogen, resulting in the formation of a double bond. - **Newman Projection:** Needs to be drawn along the bond undergoing elimination to determine E/Z configuration. 2. **Second Reaction:** - **Structure:** Similar to the first, this molecule also features a bromine on a cycloalkyl group. The configuration of the bromine is shown with a solid wedge, indicating its position relative to the plane. - **Mechanism:** The E2 reaction proceeds with the removal of bromine and a hydrogen atom to form a double bond. - **Newman Projection:** To discern the stereochemistry (E/Z), a Newman projection is necessary, focusing on the anti-periplanar arrangement of hydrogen and bromine. In both scenarios, following the E2 mechanism will lead to the formation of a stable alkene. The stereochemistry should be analyzed through Newman projections to predict whether the resulting alkene will exhibit E (trans) or Z (cis) configuration, which is critical for understanding the diastereomeric outcomes.
Transcribed Image Text:**4. Each of the following alkyl bromides gives only one product via an E2 mechanism. Provide the mechanism and the product for each of the following reactions. Draw Newman projections to determine the E/Z diastereomers.** **Description of Diagrams:** The image contains two chemical structures, each related to an E2 elimination reaction involving alkyl bromides. 1. **First Reaction:** - **Structure:** A bromine atom (Br) is attached to a benzene ring (cyclohexane) linked to a carbon chain. The carbon adjacent to the bromine displays a solid wedge, indicating the bromine is coming out of the plane. The hydrogen (not shown) would ideally be anti-periplanar for the E2 reaction to occur efficiently. - **Mechanism:** The E2 mechanism requires the elimination of the bromine atom and the beta hydrogen, resulting in the formation of a double bond. - **Newman Projection:** Needs to be drawn along the bond undergoing elimination to determine E/Z configuration. 2. **Second Reaction:** - **Structure:** Similar to the first, this molecule also features a bromine on a cycloalkyl group. The configuration of the bromine is shown with a solid wedge, indicating its position relative to the plane. - **Mechanism:** The E2 reaction proceeds with the removal of bromine and a hydrogen atom to form a double bond. - **Newman Projection:** To discern the stereochemistry (E/Z), a Newman projection is necessary, focusing on the anti-periplanar arrangement of hydrogen and bromine. In both scenarios, following the E2 mechanism will lead to the formation of a stable alkene. The stereochemistry should be analyzed through Newman projections to predict whether the resulting alkene will exhibit E (trans) or Z (cis) configuration, which is critical for understanding the diastereomeric outcomes.
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