Propose best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible). Note: Some compounds cannot be made using Williamson synthesis reaction. A: B: C: OH OH KH KH -OK OK Br SN2 Br SN1 Cannot be synthesized using Williamson ether syntheses.
Propose best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible). Note: Some compounds cannot be made using Williamson synthesis reaction. A: B: C: OH OH KH KH -OK OK Br SN2 Br SN1 Cannot be synthesized using Williamson ether syntheses.
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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**Option A:**
1. Starting Material: t-Butyl alcohol (t-BuOH)
2. Process: Treated with potassium hydride (KH) to form the t-butoxide ion (t-BuOK) and potassium cation, eliminating hydrogen gas.
3. Intermediate: t-Butoxide ion (t-BuOK)
4. Next Step: Reacted with benzyl bromide (PhCH2Br) via an S_N2 mechanism.
**Option B:**
1. Starting Material: Benzyl alcohol (PhCH2OH)
2. Process: Treated with potassium hydride (KH) to form the benzyloxide ion (PhCH2OK) and potassium cation, eliminating hydrogen gas.
3. Intermediate: Benzyloxide ion (PhCH2OK)
4. Next Step: Reacted with t-butyl bromide (t-BuBr) via an S_N1 mechanism.
**Option C:**
- **Note**: The compound cannot be synthesized using Williamson ether synthesis.
This representation provides a clear understanding of which synthetic routes are appropriate for achieving the target ether compound using Williamson ether synthesis, highlighting the correct reagents and mechanisms involved in each step.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4bb9e18c-70fc-4215-b182-b6a4a136308d%2F9b4bce2e-30c4-4c38-b76b-8a1e58140d1d%2Fuwo09m_processed.png&w=3840&q=75)
Transcribed Image Text:Propose best **Williamson ether syntheses** for the following compounds. Select all applicable options (multiple answers can be possible).
**Note:** Some compounds cannot be made using Williamson synthesis reaction.
**Diagram Explanation:**
The image illustrates various synthetic routes for producing the desired ether compound shown in the top-right corner, which features a t-butyl group attached to an ethereal oxygen and a phenyl group:
**Option A:**
1. Starting Material: t-Butyl alcohol (t-BuOH)
2. Process: Treated with potassium hydride (KH) to form the t-butoxide ion (t-BuOK) and potassium cation, eliminating hydrogen gas.
3. Intermediate: t-Butoxide ion (t-BuOK)
4. Next Step: Reacted with benzyl bromide (PhCH2Br) via an S_N2 mechanism.
**Option B:**
1. Starting Material: Benzyl alcohol (PhCH2OH)
2. Process: Treated with potassium hydride (KH) to form the benzyloxide ion (PhCH2OK) and potassium cation, eliminating hydrogen gas.
3. Intermediate: Benzyloxide ion (PhCH2OK)
4. Next Step: Reacted with t-butyl bromide (t-BuBr) via an S_N1 mechanism.
**Option C:**
- **Note**: The compound cannot be synthesized using Williamson ether synthesis.
This representation provides a clear understanding of which synthetic routes are appropriate for achieving the target ether compound using Williamson ether synthesis, highlighting the correct reagents and mechanisms involved in each step.
![### Williamson Ether Synthesis
**Objective:**
Propose the best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible).
**Note:** Some compounds cannot be made using the Williamson synthesis reaction.
#### Compound A:
**Starting Materials:**
Ethyl alcohol (ethanol) reacts in the following steps:
1. \( \text{C}_2\text{H}_5\text{OH} + \text{Na} \rightarrow \text{C}_2\text{H}_5\text{O}^- \text{Na}^+ \)
2. The resulting ethoxide ion reacts with chlorobenzene:
\[ \text{C}_2\text{H}_5\text{O}^- \text{Na}^+ + \text{C}_6\text{H}_5\text{CH}_2\text{Cl} \rightarrow \text{C}_2\text{H}_5\text{OCH}_2\text{C}_6\text{H}_5} + \text{NaCl} \]
**Diagram Explanation:**
- **First Step:** Ethanol is deprotonated by sodium (Na) to form sodium ethoxide.
- **Second Step:** Sodium ethoxide undergoes an S\(_N2\) reaction with benzyl chloride.
#### Compound B:
**Starting Materials:**
Benzyl alcohol reacts in the following steps:
1. \( \text{C}_6\text{H}_5\text{CH}_2\text{OH} + \text{NaH} \rightarrow \text{C}_6\text{H}_5\text{CH}_2\text{O}^- \text{Na}^+ \)
2. The resulting benzyl oxide ion reacts with ethyl bromide:
\[ \text{C}_6\text{H}_5\text{CH}_2\text{O}^- \text{Na}^+ + \text{C}_2\text{H}_5\text{Br} \rightarrow \text{C}_6\text{H}_5\text{CH}_2\text{OCH}_2\text{C}_2\text{H}_5 + \text{NaBr} \]
**Diagram Explanation:**
- **First Step:**](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4bb9e18c-70fc-4215-b182-b6a4a136308d%2F9b4bce2e-30c4-4c38-b76b-8a1e58140d1d%2Frgmtcbf_processed.png&w=3840&q=75)
Transcribed Image Text:### Williamson Ether Synthesis
**Objective:**
Propose the best Williamson ether syntheses for the following compounds. Select all applicable options (multiple answers can be possible).
**Note:** Some compounds cannot be made using the Williamson synthesis reaction.
#### Compound A:
**Starting Materials:**
Ethyl alcohol (ethanol) reacts in the following steps:
1. \( \text{C}_2\text{H}_5\text{OH} + \text{Na} \rightarrow \text{C}_2\text{H}_5\text{O}^- \text{Na}^+ \)
2. The resulting ethoxide ion reacts with chlorobenzene:
\[ \text{C}_2\text{H}_5\text{O}^- \text{Na}^+ + \text{C}_6\text{H}_5\text{CH}_2\text{Cl} \rightarrow \text{C}_2\text{H}_5\text{OCH}_2\text{C}_6\text{H}_5} + \text{NaCl} \]
**Diagram Explanation:**
- **First Step:** Ethanol is deprotonated by sodium (Na) to form sodium ethoxide.
- **Second Step:** Sodium ethoxide undergoes an S\(_N2\) reaction with benzyl chloride.
#### Compound B:
**Starting Materials:**
Benzyl alcohol reacts in the following steps:
1. \( \text{C}_6\text{H}_5\text{CH}_2\text{OH} + \text{NaH} \rightarrow \text{C}_6\text{H}_5\text{CH}_2\text{O}^- \text{Na}^+ \)
2. The resulting benzyl oxide ion reacts with ethyl bromide:
\[ \text{C}_6\text{H}_5\text{CH}_2\text{O}^- \text{Na}^+ + \text{C}_2\text{H}_5\text{Br} \rightarrow \text{C}_6\text{H}_5\text{CH}_2\text{OCH}_2\text{C}_2\text{H}_5 + \text{NaBr} \]
**Diagram Explanation:**
- **First Step:**
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