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5. Provide the product/s for the following reactions. Indicate if the reactions proceed via an SN1, or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. a) Br NaOCH3 H,O b) NaOCH3 H,O

5. Provide the product/s for the following reactions. Indicate if the reactions proceed via an SN1, or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. a) Br NaOCH3 H,O b) NaOCH3 H,O

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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parts a and b

**Problem 5:** Provide the product/s for the following reactions. Indicate if the reactions proceed via an SN1 or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. **a) Reaction:** - **Substrate:** 4-bromo-3-methyl-1-pentene - **Reagent:** Sodium methoxide (NaOCH₃) in water (H₂O) **Analysis:** The substrate is a primary allylic halide, which favors the SN2 mechanism due to less steric hindrance and the presence of a good leaving group (Br). The involvement of NaOCH₃ (a strong nucleophile) suggests an SN2 reaction, resulting in the inversion of configuration at the reactive carbon center. The product will include a methoxy group replacing the bromine atom. **b) Reaction:** - **Substrate:** 1-chloro-3-methylcyclohexane - **Reagent:** Sodium methoxide (NaOCH₃) in water (H₂O) **Analysis:** The substrate is a secondary alkyl chloride, suitable for either SN1 or SN2. Given that NaOCH₃ is a strong base and a strong nucleophile, the SN2 pathway is more likely, which involves backside attack and stereochemical inversion. The reaction will replace the chlorine atom with a methoxy group, with inversion of configuration at the chiral center. **Note:** Specific diagrams of the reaction mechanisms and the exact stereochemical configurations of products must be drawn to fully represent the stereochemical outcomes, but the provided answer outlines the predicted products and mechanisms.
Transcribed Image Text:**Problem 5:** Provide the product/s for the following reactions. Indicate if the reactions proceed via an SN1 or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. **a) Reaction:** - **Substrate:** 4-bromo-3-methyl-1-pentene - **Reagent:** Sodium methoxide (NaOCH₃) in water (H₂O) **Analysis:** The substrate is a primary allylic halide, which favors the SN2 mechanism due to less steric hindrance and the presence of a good leaving group (Br). The involvement of NaOCH₃ (a strong nucleophile) suggests an SN2 reaction, resulting in the inversion of configuration at the reactive carbon center. The product will include a methoxy group replacing the bromine atom. **b) Reaction:** - **Substrate:** 1-chloro-3-methylcyclohexane - **Reagent:** Sodium methoxide (NaOCH₃) in water (H₂O) **Analysis:** The substrate is a secondary alkyl chloride, suitable for either SN1 or SN2. Given that NaOCH₃ is a strong base and a strong nucleophile, the SN2 pathway is more likely, which involves backside attack and stereochemical inversion. The reaction will replace the chlorine atom with a methoxy group, with inversion of configuration at the chiral center. **Note:** Specific diagrams of the reaction mechanisms and the exact stereochemical configurations of products must be drawn to fully represent the stereochemical outcomes, but the provided answer outlines the predicted products and mechanisms.
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