**Part I (Quantitative):** A substitution reaction using the tertiary diol below will produce a product that can be isolated and characterized. - **Chemical Reaction:** - Reactants: 2,5-dimethylhexane-2,5-diol - Reagent: concentrated HCl - Product: 2,5-dichloro-2,5-dimethylhexane - Melting Point: 63–66.5 °C **Part II (Qualitative):** The substitution of various alkyl halides will provide insight into the effects of substrate structure, leaving group, and reaction temperature on \( S_N2 \) and \( S_N1 \) reactions. You will be able to draw conclusions about these reactions based on your observations. The available alkyl halides are listed later in the experimental procedures section. - **Available Reaction Solutions:** - 18% sodium iodide in acetone - 1% silver nitrate in ethanol **Instructions:** **For Part I (Quantitative):** - **a.** Draw the overall synthetic reaction, including all structures, relevant physical data, amounts, and safety information. - **b.** Clearly show the calculation (including units throughout) of the theoretical yield of the reaction. Indicate the limiting reagent. **For Part II (Qualitative):** - **c.** Include the names and structures of all alkyl halides, as well as the structures and physical properties of other reagents used. Quantities of alkyl halides and reagents are not necessary for Part II. **Questions:** 1. Based on your understanding of factors that influence \( S_N2 \) and \( S_N1 \) reactions, briefly explain whether the sodium iodide/acetone solution will favor an \( S_N2 \) or \( S_N1 \) reaction. 2. Based on your understanding of factors that influence \( S_N2 \) and \( S_N1 \) reactions, briefly explain whether the silver nitrate/ethanol solution will favor an \( S_N2 \) or \( S_N1 \) reaction. 3. Explain why a trichloroacetimidate is a good leaving group. You should include structures in your answer.

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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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**Part I (Quantitative):** A substitution reaction using the tertiary diol below will produce a product that can be isolated and characterized.

- **Chemical Reaction:**
  - Reactants: 2,5-dimethylhexane-2,5-diol
  - Reagent: concentrated HCl
  - Product: 2,5-dichloro-2,5-dimethylhexane 
  - Melting Point: 63–66.5 °C

**Part II (Qualitative):** The substitution of various alkyl halides will provide insight into the effects of substrate structure, leaving group, and reaction temperature on \( S_N2 \) and \( S_N1 \) reactions. You will be able to draw conclusions about these reactions based on your observations. The available alkyl halides are listed later in the experimental procedures section.

- **Available Reaction Solutions:**
  - 18% sodium iodide in acetone
  - 1% silver nitrate in ethanol

**Instructions:**

**For Part I (Quantitative):**
- **a.** Draw the overall synthetic reaction, including all structures, relevant physical data, amounts, and safety information.
- **b.** Clearly show the calculation (including units throughout) of the theoretical yield of the reaction. Indicate the limiting reagent.

**For Part II (Qualitative):**
- **c.** Include the names and structures of all alkyl halides, as well as the structures and physical properties of other reagents used. Quantities of alkyl halides and reagents are not necessary for Part II.

**Questions:**
1. Based on your understanding of factors that influence \( S_N2 \) and \( S_N1 \) reactions, briefly explain whether the sodium iodide/acetone solution will favor an \( S_N2 \) or \( S_N1 \) reaction.
2. Based on your understanding of factors that influence \( S_N2 \) and \( S_N1 \) reactions, briefly explain whether the silver nitrate/ethanol solution will favor an \( S_N2 \) or \( S_N1 \) reaction.
3. Explain why a trichloroacetimidate is a good leaving group. You should include structures in your answer.
Transcribed Image Text:**Part I (Quantitative):** A substitution reaction using the tertiary diol below will produce a product that can be isolated and characterized. - **Chemical Reaction:** - Reactants: 2,5-dimethylhexane-2,5-diol - Reagent: concentrated HCl - Product: 2,5-dichloro-2,5-dimethylhexane - Melting Point: 63–66.5 °C **Part II (Qualitative):** The substitution of various alkyl halides will provide insight into the effects of substrate structure, leaving group, and reaction temperature on \( S_N2 \) and \( S_N1 \) reactions. You will be able to draw conclusions about these reactions based on your observations. The available alkyl halides are listed later in the experimental procedures section. - **Available Reaction Solutions:** - 18% sodium iodide in acetone - 1% silver nitrate in ethanol **Instructions:** **For Part I (Quantitative):** - **a.** Draw the overall synthetic reaction, including all structures, relevant physical data, amounts, and safety information. - **b.** Clearly show the calculation (including units throughout) of the theoretical yield of the reaction. Indicate the limiting reagent. **For Part II (Qualitative):** - **c.** Include the names and structures of all alkyl halides, as well as the structures and physical properties of other reagents used. Quantities of alkyl halides and reagents are not necessary for Part II. **Questions:** 1. Based on your understanding of factors that influence \( S_N2 \) and \( S_N1 \) reactions, briefly explain whether the sodium iodide/acetone solution will favor an \( S_N2 \) or \( S_N1 \) reaction. 2. Based on your understanding of factors that influence \( S_N2 \) and \( S_N1 \) reactions, briefly explain whether the silver nitrate/ethanol solution will favor an \( S_N2 \) or \( S_N1 \) reaction. 3. Explain why a trichloroacetimidate is a good leaving group. You should include structures in your answer.
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