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6. Determine whether each reaction occurs by an Sn2, Sn1, E1, and/or E2 reaction. Provide a detailed mechanism with curved arrows and the major product(s). CI NaSH DMF OMs NaOH H20, heat LDA Br DMF NaOH Br H20, heat Он HBr он H*, H2O heat

6. Determine whether each reaction occurs by an Sn2, Sn1, E1, and/or E2 reaction. Provide a detailed mechanism with curved arrows and the major product(s). CI NaSH DMF OMs NaOH H20, heat LDA Br DMF NaOH Br H20, heat Он HBr он H*, H2O heat

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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**Exercise 6: Reaction Mechanisms** **Task:** Determine the mechanism type for each reaction (Sn2, Sn1, E1, and/or E2). Provide a detailed mechanism using curved arrows and identify the major product(s). **Reactions:** 1. **Cycloheptyl Chloride Reaction:** - Reactant: Cycloheptyl chloride - Reagents: NaSH, DMF (Dimethylformamide) - Reaction: - The chloride is replaced by a sulfide ion (from NaSH). Consider possible Sn2 or E2 pathways. 2. **Cyclohexyl Methanesulfonate Reaction:** - Reactant: Cyclohexyl methanesulfonate (OMs) - Reagents: NaOH, water, heat - Reaction: - Methanesulfonate is a good leaving group. Analyze for E1 or E2 mechanism due to heat. 3. **3-Bromohexane Reaction:** - Reactant: 3-Bromohexane - Reagents: LDA (Lithium diisopropylamide), DMF - Reaction: - LDA is a strong base, suggesting E2 elimination to form an alkene. 4. **Cyclopentyl Bromide Reaction:** - Reactant: Cyclopentyl bromide - Reagents: NaOH, water, heat - Reaction: - High temperature favors elimination. Check for E2 mechanism. 5. **Tert-butanol Reaction:** - Reactant: Tert-butanol - Reagents: HBr - Reaction: - Alcohol conversion to alkyl bromide. Sn1 mechanism is likely due to tertiary alcohol. 6. **Phenethyl Alcohol Reaction:** - Reactant: Phenethyl alcohol - Reagents: H⁺, water, heat - Reaction: - Presence of acid and heat hints at dehydration via E1 mechanism to produce an alkene. **Diagram and Mechanism Explanation:** - Each reaction shows a starting organic compound with specific reagents leading to products. - Curved arrows should demonstrate: - Movement of electrons during bond breaking/forming. - Intermediate states and transition states if applicable. - Major products should be identified based on mechanism predictions (nucleophilic substitution vs
Transcribed Image Text:**Exercise 6: Reaction Mechanisms** **Task:** Determine the mechanism type for each reaction (Sn2, Sn1, E1, and/or E2). Provide a detailed mechanism using curved arrows and identify the major product(s). **Reactions:** 1. **Cycloheptyl Chloride Reaction:** - Reactant: Cycloheptyl chloride - Reagents: NaSH, DMF (Dimethylformamide) - Reaction: - The chloride is replaced by a sulfide ion (from NaSH). Consider possible Sn2 or E2 pathways. 2. **Cyclohexyl Methanesulfonate Reaction:** - Reactant: Cyclohexyl methanesulfonate (OMs) - Reagents: NaOH, water, heat - Reaction: - Methanesulfonate is a good leaving group. Analyze for E1 or E2 mechanism due to heat. 3. **3-Bromohexane Reaction:** - Reactant: 3-Bromohexane - Reagents: LDA (Lithium diisopropylamide), DMF - Reaction: - LDA is a strong base, suggesting E2 elimination to form an alkene. 4. **Cyclopentyl Bromide Reaction:** - Reactant: Cyclopentyl bromide - Reagents: NaOH, water, heat - Reaction: - High temperature favors elimination. Check for E2 mechanism. 5. **Tert-butanol Reaction:** - Reactant: Tert-butanol - Reagents: HBr - Reaction: - Alcohol conversion to alkyl bromide. Sn1 mechanism is likely due to tertiary alcohol. 6. **Phenethyl Alcohol Reaction:** - Reactant: Phenethyl alcohol - Reagents: H⁺, water, heat - Reaction: - Presence of acid and heat hints at dehydration via E1 mechanism to produce an alkene. **Diagram and Mechanism Explanation:** - Each reaction shows a starting organic compound with specific reagents leading to products. - Curved arrows should demonstrate: - Movement of electrons during bond breaking/forming. - Intermediate states and transition states if applicable. - Major products should be identified based on mechanism predictions (nucleophilic substitution vs
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