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Draw the product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. Br CH3CO2Na THF

Draw the product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. Br CH3CO2Na THF

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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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### SN2 Reaction Mechanism #### Task: Draw the product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. #### Reactants: - **Starting Compound**: A benzene ring with a bromomethyl group attached. The bromine atom is shown with a wedge bond, indicating its stereochemical position. - **Reagents**: - Sodium acetate (CH₃CO₂Na) - Solvent: Tetrahydrofuran (THF) #### Reaction Description: The given reaction involves an SN2 (bimolecular nucleophilic substitution) mechanism. In this reaction, the bromine acts as a leaving group, and the acetate ion (CH₃CO₂⁻) from sodium acetate serves as the nucleophile that will attack the electrophilic carbon center. #### Expected Outcome: - **Inversion of Stereochemistry**: In an SN2 reaction, the nucleophile attacks from the opposite side to the leaving group, resulting in an inversion of stereochemistry at the chiral center. Here, the nucleophile attacks the carbon atom bonded to bromine, displacing the bromine ion as a leaving group and forming a new bond with the acetate group. ### Explanation of Stereochemistry: - **Wedge and Dash Bonds**: The wedge indicates the bond projecting out of the plane towards the viewer, and the dash indicates a bond going into the plane away from the viewer. The final product should reflect an inversion where the new acetate group assumes the position previously occupied by the bromine atom, but in the opposite spatial configuration. This reaction is typical within organic chemistry courses to illustrate nucleophilic substitution where stereochemistry is crucial to the structure and properties of the resulting product.
Transcribed Image Text:### SN2 Reaction Mechanism #### Task: Draw the product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. #### Reactants: - **Starting Compound**: A benzene ring with a bromomethyl group attached. The bromine atom is shown with a wedge bond, indicating its stereochemical position. - **Reagents**: - Sodium acetate (CH₃CO₂Na) - Solvent: Tetrahydrofuran (THF) #### Reaction Description: The given reaction involves an SN2 (bimolecular nucleophilic substitution) mechanism. In this reaction, the bromine acts as a leaving group, and the acetate ion (CH₃CO₂⁻) from sodium acetate serves as the nucleophile that will attack the electrophilic carbon center. #### Expected Outcome: - **Inversion of Stereochemistry**: In an SN2 reaction, the nucleophile attacks from the opposite side to the leaving group, resulting in an inversion of stereochemistry at the chiral center. Here, the nucleophile attacks the carbon atom bonded to bromine, displacing the bromine ion as a leaving group and forming a new bond with the acetate group. ### Explanation of Stereochemistry: - **Wedge and Dash Bonds**: The wedge indicates the bond projecting out of the plane towards the viewer, and the dash indicates a bond going into the plane away from the viewer. The final product should reflect an inversion where the new acetate group assumes the position previously occupied by the bromine atom, but in the opposite spatial configuration. This reaction is typical within organic chemistry courses to illustrate nucleophilic substitution where stereochemistry is crucial to the structure and properties of the resulting product.
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