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11. 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). OMs Br Br OH мон OH NaSH DMF NaOH H₂O, heat LDA DMF NaOH H₂O, heat HBr H, H₂O heat

11. 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). OMs Br Br OH мон OH NaSH DMF NaOH H₂O, heat LDA DMF NaOH H₂O, heat HBr H, H₂O heat

Chemistry
Chemistry
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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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**Exercise 11: Reaction Mechanisms** 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). 1. **Reaction 1** - **Starting Material:** Cyclohexyl chloride - **Reagent:** NaSH - **Solvent:** DMF - **Mechanism:** Typically occurs via an Sn2 reaction due to the strong nucleophile (NaSH) and polar aprotic solvent (DMF). The product would involve the substitution of the chlorine with SH. 2. **Reaction 2** - **Starting Material:** Cyclohexyl methanesulfonate - **Reagent:** NaOH, H₂O, heat - **Mechanism:** Likely proceeds through an E2 mechanism. The product would be a cyclohexene due to elimination. 3. **Reaction 3** - **Starting Material:** 1-bromo-2-methylpentane - **Reagent:** LDA - **Solvent:** DMF - **Mechanism:** An E2 reaction is favored due to the strong base (LDA) and polar aprotic solvent (DMF). The product will involve dehydrohalogenation resulting in an alkene. 4. **Reaction 4** - **Starting Material:** Bromocyclopentane - **Reagent:** NaOH, H₂O, heat - **Mechanism:** Proceeds through an E2 mechanism forming cyclopentene due to elimination. 5. **Reaction 5** - **Starting Material:** 2-methyl-2-propanol - **Reagent:** HBr - **Mechanism:** Occurs via an Sn1 reaction. The product is a result of substitution where the hydroxyl group is replaced by bromine. 6. **Reaction 6** - **Starting Material:** Phenylethanol - **Reagent:** H⁺, H₂O, heat - **Mechanism:** Likely to proceed through an E1 mechanism resulting in the formation of an alkene as the major product due to dehydration. **Diagram Explanation:** - **Structures**: Each reaction depicts a structural formula of the starting organic compound. - **Reagents and Conditions**: Listed above the reaction arrow
Transcribed Image Text:**Exercise 11: Reaction Mechanisms** 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). 1. **Reaction 1** - **Starting Material:** Cyclohexyl chloride - **Reagent:** NaSH - **Solvent:** DMF - **Mechanism:** Typically occurs via an Sn2 reaction due to the strong nucleophile (NaSH) and polar aprotic solvent (DMF). The product would involve the substitution of the chlorine with SH. 2. **Reaction 2** - **Starting Material:** Cyclohexyl methanesulfonate - **Reagent:** NaOH, H₂O, heat - **Mechanism:** Likely proceeds through an E2 mechanism. The product would be a cyclohexene due to elimination. 3. **Reaction 3** - **Starting Material:** 1-bromo-2-methylpentane - **Reagent:** LDA - **Solvent:** DMF - **Mechanism:** An E2 reaction is favored due to the strong base (LDA) and polar aprotic solvent (DMF). The product will involve dehydrohalogenation resulting in an alkene. 4. **Reaction 4** - **Starting Material:** Bromocyclopentane - **Reagent:** NaOH, H₂O, heat - **Mechanism:** Proceeds through an E2 mechanism forming cyclopentene due to elimination. 5. **Reaction 5** - **Starting Material:** 2-methyl-2-propanol - **Reagent:** HBr - **Mechanism:** Occurs via an Sn1 reaction. The product is a result of substitution where the hydroxyl group is replaced by bromine. 6. **Reaction 6** - **Starting Material:** Phenylethanol - **Reagent:** H⁺, H₂O, heat - **Mechanism:** Likely to proceed through an E1 mechanism resulting in the formation of an alkene as the major product due to dehydration. **Diagram Explanation:** - **Structures**: Each reaction depicts a structural formula of the starting organic compound. - **Reagents and Conditions**: Listed above the reaction arrow
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