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25. Determine whether the following reaction proceeds via an SN1 or an SN2 mechanism and product(s) of the reaction ? H-Br NaCN DMF OTS (d) H20 Br NaCN DMSO (f)

25. Determine whether the following reaction proceeds via an SN1 or an SN2 mechanism and product(s) of the reaction ? H-Br NaCN DMF OTS (d) H20 Br NaCN DMSO (f)

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
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**Title: Determining SN1 or SN2 Mechanisms and Reaction Products** **Question 25:** Determine whether the following reaction proceeds via an SN1 or an SN2 mechanism and identify the product(s) of the reaction. **Reactants and Conditions:** 1. **First Reaction:** - Substrate: A secondary alcohol. - Reagent: HBr. - Mechanism Question: Is it SN1 or SN2? 2. **Second Reaction:** - Substrate: A secondary alkyl iodide. - Reagent: H₂O. - Mechanism Question: Does this proceed via SN1 or SN2? 3. **Third Reaction (d):** - Substrate: Ethyl tosylate (OTs). - Reagent: NaCN in DMF. - Mechanism Question: Determine the mechanism (SN1 or SN2) and predict the product. 4. **Fourth Reaction (f):** - Substrate: Cyclohexyl bromide. - Reagent: NaCN in DMSO. - Mechanism Question: Determine the mechanism (SN1 or SN2) and predict the product. **Explanation:** - **SN1 Mechanism:** - Typically involves tertiary substrates or secondary substrates in polar protic solvents. - Proceeds through a carbocation intermediate. - Reaction rate is unimolecular, depending solely on the concentration of the substrate. - **SN2 Mechanism:** - Usually occurs with primary or secondary substrates in polar aprotic solvents. - Involves a direct nucleophilic attack, leading to a single transition state. - Reaction rate is bimolecular, depending on the concentration of both the substrate and the nucleophile. Remember to consider factors such as substrate structure, solvent type, and reagent strength when determining the likely reaction mechanism and products.
Transcribed Image Text:**Title: Determining SN1 or SN2 Mechanisms and Reaction Products** **Question 25:** Determine whether the following reaction proceeds via an SN1 or an SN2 mechanism and identify the product(s) of the reaction. **Reactants and Conditions:** 1. **First Reaction:** - Substrate: A secondary alcohol. - Reagent: HBr. - Mechanism Question: Is it SN1 or SN2? 2. **Second Reaction:** - Substrate: A secondary alkyl iodide. - Reagent: H₂O. - Mechanism Question: Does this proceed via SN1 or SN2? 3. **Third Reaction (d):** - Substrate: Ethyl tosylate (OTs). - Reagent: NaCN in DMF. - Mechanism Question: Determine the mechanism (SN1 or SN2) and predict the product. 4. **Fourth Reaction (f):** - Substrate: Cyclohexyl bromide. - Reagent: NaCN in DMSO. - Mechanism Question: Determine the mechanism (SN1 or SN2) and predict the product. **Explanation:** - **SN1 Mechanism:** - Typically involves tertiary substrates or secondary substrates in polar protic solvents. - Proceeds through a carbocation intermediate. - Reaction rate is unimolecular, depending solely on the concentration of the substrate. - **SN2 Mechanism:** - Usually occurs with primary or secondary substrates in polar aprotic solvents. - Involves a direct nucleophilic attack, leading to a single transition state. - Reaction rate is bimolecular, depending on the concentration of both the substrate and the nucleophile. Remember to consider factors such as substrate structure, solvent type, and reagent strength when determining the likely reaction mechanism and products.
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