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3. For each of the following compounds provide appropriate reactants and solvent SN2 systems to synthesize them by a substitution reaction. Show which type of substitution: SN1 or SN2. cannar Br NH2 Br NaCN NH3 acetone CN can メ ズ Br OH HBr Super NASH Br DMSO SH Nay happing

3. For each of the following compounds provide appropriate reactants and solvent SN2 systems to synthesize them by a substitution reaction. Show which type of substitution: SN1 or SN2. cannar Br NH2 Br NaCN NH3 acetone CN can メ ズ Br OH HBr Super NASH Br DMSO SH Nay happing

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
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Substitution Reactions: S<sub>N1</sub> and S<sub>N2</sub> Mechanisms** In this exercise, we explore appropriate reactants and solvents to achieve specific substitution reactions with given compounds. Each method will be identified as an S<sub>N1</sub> or S<sub>N2</sub> process based on the reaction conditions. ### Reaction 1: - **Starting Material:** Alkyl bromide - **Reagent and Solvent:** NaCN in acetone - **Product:** Alkyl cyanide - **Mechanism Type:** S<sub>N2</sub> - **Notes:** The reaction proceeds via an S<sub>N2</sub> mechanism, suitable for primary or secondary carbon centers due to less steric hindrance. ### Reaction 2: - **Starting Material:** Alcohol - **Reagent:** HBr - **Product:** Alkyl bromide - **Mechanism Type:** S<sub>N1</sub> - **Notes:** This tertiary alcohol undergoes substitution via an S<sub>N1</sub> mechanism due to carbocation stability. ### Reaction 3: - **Starting Material:** Bromocyclopentane - **Reagent:** NH<sub>3</sub> (Ammonia) - **Product:** Aminocyclopentane - **Mechanism Type:** S<sub>N2</sub> - **Notes:** Despite being cycloalkane, the steric environment allows for S<sub>N2</sub> substitution in the presence of a strong nucleophile like NH<sub>3</sub>. ### Reaction 4: - **Starting Material:** Cyclohexyl bromide - **Reagent and Solvent:** NaSH in DMSO - **Product:** Thiol derivative - **Mechanism Type:** S<sub>N1</sub> - **Notes:** The nature of the solvent and the bulkiness of the nucleophile contribute to a preference for an S<sub>N1</sub> mechanism. **Handwritten Annotations:** - "S<sub>N2</sub> cannot undergo tertiary": Emphasizes why S<sub>N2</sub> isn't favored in certain reactions due to steric hindrance. - "S<sub>N2</sub> can": Indicates conditions under which an S<sub>N2</sub> reaction is favorable. - "
Transcribed Image Text:**Substitution Reactions: S<sub>N1</sub> and S<sub>N2</sub> Mechanisms** In this exercise, we explore appropriate reactants and solvents to achieve specific substitution reactions with given compounds. Each method will be identified as an S<sub>N1</sub> or S<sub>N2</sub> process based on the reaction conditions. ### Reaction 1: - **Starting Material:** Alkyl bromide - **Reagent and Solvent:** NaCN in acetone - **Product:** Alkyl cyanide - **Mechanism Type:** S<sub>N2</sub> - **Notes:** The reaction proceeds via an S<sub>N2</sub> mechanism, suitable for primary or secondary carbon centers due to less steric hindrance. ### Reaction 2: - **Starting Material:** Alcohol - **Reagent:** HBr - **Product:** Alkyl bromide - **Mechanism Type:** S<sub>N1</sub> - **Notes:** This tertiary alcohol undergoes substitution via an S<sub>N1</sub> mechanism due to carbocation stability. ### Reaction 3: - **Starting Material:** Bromocyclopentane - **Reagent:** NH<sub>3</sub> (Ammonia) - **Product:** Aminocyclopentane - **Mechanism Type:** S<sub>N2</sub> - **Notes:** Despite being cycloalkane, the steric environment allows for S<sub>N2</sub> substitution in the presence of a strong nucleophile like NH<sub>3</sub>. ### Reaction 4: - **Starting Material:** Cyclohexyl bromide - **Reagent and Solvent:** NaSH in DMSO - **Product:** Thiol derivative - **Mechanism Type:** S<sub>N1</sub> - **Notes:** The nature of the solvent and the bulkiness of the nucleophile contribute to a preference for an S<sub>N1</sub> mechanism. **Handwritten Annotations:** - "S<sub>N2</sub> cannot undergo tertiary": Emphasizes why S<sub>N2</sub> isn't favored in certain reactions due to steric hindrance. - "S<sub>N2</sub> can": Indicates conditions under which an S<sub>N2</sub> reaction is favorable. - "
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