2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice. Compound A

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**Question:**

2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice.

**Diagram Explanation:**

The image includes a structural diagram of Compound A, which is an ether composed of an isopropyl group (a branching with two methyl groups attached to a central carbon) linked via an oxygen atom to a methyl group.

**Discussion:**

To prepare Compound A using Williamson Ether Synthesis, there are two possible approaches involving different alkyl halides and alkoxides:

1. **Route 1:**
   - **Starting Materials:** Isopropyl alcohol to form isopropoxide ion and methyl iodide.
   - **Reaction:** Isopropoxide ion acts as a nucleophile and displaces the iodide ion from methyl iodide via an S_N2 reaction, forming Compound A.

2. **Route 2:**
   - **Starting Materials:** Methyl alcohol to form methoxide ion and isopropyl iodide.
   - **Reaction:** Methoxide ion attacks the isopropyl iodide, displacing iodide ion via an S_N2 mechanism to form Compound A.

**Preferred Route:**

Route 1 is preferred because:
- S_N2 reactions are more favorable with less steric hindrance. Methyl iodide offers less steric hindrance compared to isopropyl iodide, making the reaction with isopropoxide ion more efficient and faster.
- The formation of isopropoxide from isopropyl alcohol is generally more accessible and results in a more reactive alkoxide for the desired synthesis.

By selecting Route 1, the reaction conditions are more favorable, resulting in a higher yield and more efficient synthesis of Compound A.
Transcribed Image Text:**Question:** 2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice. **Diagram Explanation:** The image includes a structural diagram of Compound A, which is an ether composed of an isopropyl group (a branching with two methyl groups attached to a central carbon) linked via an oxygen atom to a methyl group. **Discussion:** To prepare Compound A using Williamson Ether Synthesis, there are two possible approaches involving different alkyl halides and alkoxides: 1. **Route 1:** - **Starting Materials:** Isopropyl alcohol to form isopropoxide ion and methyl iodide. - **Reaction:** Isopropoxide ion acts as a nucleophile and displaces the iodide ion from methyl iodide via an S_N2 reaction, forming Compound A. 2. **Route 2:** - **Starting Materials:** Methyl alcohol to form methoxide ion and isopropyl iodide. - **Reaction:** Methoxide ion attacks the isopropyl iodide, displacing iodide ion via an S_N2 mechanism to form Compound A. **Preferred Route:** Route 1 is preferred because: - S_N2 reactions are more favorable with less steric hindrance. Methyl iodide offers less steric hindrance compared to isopropyl iodide, making the reaction with isopropoxide ion more efficient and faster. - The formation of isopropoxide from isopropyl alcohol is generally more accessible and results in a more reactive alkoxide for the desired synthesis. By selecting Route 1, the reaction conditions are more favorable, resulting in a higher yield and more efficient synthesis of Compound A.
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