Suppose you have compounds A-D at your disposal. Using these compounds, devise two different ways to make E. Which one of these methods is preferred, and why? Be sure to answer all parts. Part 1: CH3I Method [1]: Method [2]: Part 2: A B NaOCH3 B + C D + AV CH3OH THF D ONa E E E OCH 3 Which one of these methods is preferred, and why? Method [2] is preferred because the less substituted alkyl halide results in a more stable carbocation. Method [1] is preferred because the alkyl halide should be relatively hindered in an SN2 reaction mechanism. Method [2] is preferred because the alkyl halide should be unhindered in an S№2 reaction mechanism. Method [1] is preferred because the more substituted alkyl halide results in a more stable carbocation.

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**Title: Reaction Pathway Selection for Synthesizing Compound E**

**Introduction:**
Suppose you have compounds A-D at your disposal. Using these compounds, devise two different ways to make E. Which one of these methods is preferred, and why? Be sure to answer all parts.

**Compounds:**
- A: CH₃I
- B: Cyclohexyl iodide
- C: Sodium methoxide (NaOCH₃)
- D: Sodium cyclohexoxide (ONa)
- E: Cyclohexyl methyl ether (OCH₃)

**Part 1: Reaction Methods**

**Method [1]:**
- **Reaction:** B + C → E
- **Solvent:** CH₃OH (Methanol)

**Method [2]:**
- **Reaction:** D + A → E
- **Solvent:** THF (Tetrahydrofuran)

**Part 2: Preferred Method**

**Question: Which one of these methods is preferred, and why?**

- **Option 1:** Method [2] is preferred because the less substituted alkyl halide results in a more stable carbocation.
- **Option 2:** Method [1] is preferred because the alkyl halide should be relatively hindered in an Sₙ2 reaction mechanism.
- **Option 3:** Method [2] is preferred because the alkyl halide should be unhindered in an Sₙ2 reaction mechanism.
- **Option 4:** Method [1] is preferred because the more substituted alkyl halide results in a more stable carbocation.

**Preferred Answer:** 
- **Method [2] is preferred because the alkyl halide should be unhindered in an Sₙ2 reaction mechanism.** 

This conclusion emphasizes the advantage of using an unhindered alkyl halide in facilitating the bimolecular nucleophilic substitution (Sₙ2) mechanism, which is known for favoring primary or unhindered substrates.
Transcribed Image Text:**Title: Reaction Pathway Selection for Synthesizing Compound E** **Introduction:** Suppose you have compounds A-D at your disposal. Using these compounds, devise two different ways to make E. Which one of these methods is preferred, and why? Be sure to answer all parts. **Compounds:** - A: CH₃I - B: Cyclohexyl iodide - C: Sodium methoxide (NaOCH₃) - D: Sodium cyclohexoxide (ONa) - E: Cyclohexyl methyl ether (OCH₃) **Part 1: Reaction Methods** **Method [1]:** - **Reaction:** B + C → E - **Solvent:** CH₃OH (Methanol) **Method [2]:** - **Reaction:** D + A → E - **Solvent:** THF (Tetrahydrofuran) **Part 2: Preferred Method** **Question: Which one of these methods is preferred, and why?** - **Option 1:** Method [2] is preferred because the less substituted alkyl halide results in a more stable carbocation. - **Option 2:** Method [1] is preferred because the alkyl halide should be relatively hindered in an Sₙ2 reaction mechanism. - **Option 3:** Method [2] is preferred because the alkyl halide should be unhindered in an Sₙ2 reaction mechanism. - **Option 4:** Method [1] is preferred because the more substituted alkyl halide results in a more stable carbocation. **Preferred Answer:** - **Method [2] is preferred because the alkyl halide should be unhindered in an Sₙ2 reaction mechanism.** This conclusion emphasizes the advantage of using an unhindered alkyl halide in facilitating the bimolecular nucleophilic substitution (Sₙ2) mechanism, which is known for favoring primary or unhindered substrates.
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