But-2-yne has a pKa~ 38. Evaluate the ability of bases to deprotonate the provided acid. H H3C -H H + :B conjugate acid pKa S = (circle the most appropriate symbol) (a) What does the pKa of the conjugate acid (H-B) need to be in order to completely deprotonate but-2-yne? (Where complete deprotonation is defined as Keq≥10³.) :H H₂C > H H 2 H H + H H-B (b) Which of the following could be used as a base to completely deprotonate but-2-yne (where complete deprotonation is defined as Keq≥10³)? Circle all that could apply. (propose a value informed by the provided pKa of but-2-yne) - Он
But-2-yne has a pKa~ 38. Evaluate the ability of bases to deprotonate the provided acid. H H3C -H H + :B conjugate acid pKa S = (circle the most appropriate symbol) (a) What does the pKa of the conjugate acid (H-B) need to be in order to completely deprotonate but-2-yne? (Where complete deprotonation is defined as Keq≥10³.) :H H₂C > H H 2 H H + H H-B (b) Which of the following could be used as a base to completely deprotonate but-2-yne (where complete deprotonation is defined as Keq≥10³)? Circle all that could apply. (propose a value informed by the provided pKa of but-2-yne) - Он
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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But-2-yne has a pK.~ 38. Evaluate the ability of bases to deprotonate the provided acid.
![**Title: Evaluating the Ability of Bases to Deprotonate But-2-yne**
**Introduction:**
But-2-yne is an alkyne with a pKₐ of approximately 38. This exercise evaluates the ability of various bases to deprotonate but-2-yne completely, which is defined here as an equilibrium constant (K_eq) greater than or equal to 10³.
**Chemical Reaction:**
\[ \text{H}_3\text{C} \equiv \text{C}-\text{H} + \underline{\phantom{......}}\cdot \text{B} \rightleftharpoons \text{H}_3\text{C} \equiv \underline{\phantom{......}}\cdot + \text{H-B} \]
**Questions and Explanations:**
**(a) Determining the pKₐ of the Conjugate Acid H-B:**
- **Question:** What should the pKₐ of the conjugate acid H-B be in order to deprotonate but-2-yne completely? This is defined as achieving K_eq ≥ 10³.
- **Diagram:**
- **Conjugate acid pKₐ**: Options to select — **≤**, **=**, **≥**
- **Task:** Circle the most appropriate symbol.
- **Proposal:** Suggest a value based on the given pKₐ of but-2-yne.
**(b) Identifying Suitable Bases for Deprotonation:**
- **Question:** Which bases can be used to completely deprotonate but-2-yne, ensuring K_eq ≥ 10³? Circle all applicable bases.
- **Options:**
1. Benzyl anion (\[\underline{\phantom{......}}\])
2. Hydride ion (\[\underline{\phantom{......}}\text{H}\])
3. Methide ion (\[\underline{\phantom{......}}\text{CH}_3\])
4. Hydroxide ion (\[\underline{\phantom{......}}\text{OH}\])
**Conclusion:**
The objective is to identify bases strong enough to deprotonate but-2-yne by comparing the pKₐ values of the conjugate acids formed. Understanding this concept is essential in organic chemistry, particularly in reaction mechanisms involving alkyn](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff0cffd2c-87b7-4e41-9317-adfae3706a79%2F14fb73b5-8e28-4c92-9b70-915e8df3d31e%2Fbyjkzzu_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Evaluating the Ability of Bases to Deprotonate But-2-yne**
**Introduction:**
But-2-yne is an alkyne with a pKₐ of approximately 38. This exercise evaluates the ability of various bases to deprotonate but-2-yne completely, which is defined here as an equilibrium constant (K_eq) greater than or equal to 10³.
**Chemical Reaction:**
\[ \text{H}_3\text{C} \equiv \text{C}-\text{H} + \underline{\phantom{......}}\cdot \text{B} \rightleftharpoons \text{H}_3\text{C} \equiv \underline{\phantom{......}}\cdot + \text{H-B} \]
**Questions and Explanations:**
**(a) Determining the pKₐ of the Conjugate Acid H-B:**
- **Question:** What should the pKₐ of the conjugate acid H-B be in order to deprotonate but-2-yne completely? This is defined as achieving K_eq ≥ 10³.
- **Diagram:**
- **Conjugate acid pKₐ**: Options to select — **≤**, **=**, **≥**
- **Task:** Circle the most appropriate symbol.
- **Proposal:** Suggest a value based on the given pKₐ of but-2-yne.
**(b) Identifying Suitable Bases for Deprotonation:**
- **Question:** Which bases can be used to completely deprotonate but-2-yne, ensuring K_eq ≥ 10³? Circle all applicable bases.
- **Options:**
1. Benzyl anion (\[\underline{\phantom{......}}\])
2. Hydride ion (\[\underline{\phantom{......}}\text{H}\])
3. Methide ion (\[\underline{\phantom{......}}\text{CH}_3\])
4. Hydroxide ion (\[\underline{\phantom{......}}\text{OH}\])
**Conclusion:**
The objective is to identify bases strong enough to deprotonate but-2-yne by comparing the pKₐ values of the conjugate acids formed. Understanding this concept is essential in organic chemistry, particularly in reaction mechanisms involving alkyn
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