**Question 6:** Based on the following pKₐ values, which do you think is more important in determining inductive effects: electronegativity or distance from the reactive acidic hydrogen? Explain in 1–3 complete sentences. **Structures and pKₐ Values:** 1. Structure: A carboxylic acid molecule with a fluorine atom directly attached to the alpha carbon. - pKₐ = 2.68 2. Structure: A carboxylic acid molecule with a fluorine atom attached to the beta carbon. - pKₐ = 3.85 3. Structure: A carboxylic acid molecule with a chlorine atom directly attached to the alpha carbon. - pKₐ = 2.95 4. Structure: A carboxylic acid molecule with a chlorine atom attached to the beta carbon. - pKₐ = 3.97 **Explanation of Inductive Effects:** Inductive effects refer to the electron-withdrawing or electron-donating properties of substituents, affecting the acidity of molecules. The closer an electronegative atom like fluorine or chlorine is to the acidic hydrogen, the stronger the inductive effect is, lowering the pKₐ and therefore increasing acidity. In this example, molecules 1 and 3 (with substituents at the alpha position) have lower pKₐ values compared to molecules 2 and 4 (with substituents at the beta position), indicating that distance has a significant impact on acidity alongside electronegativity.
**Question 6:** Based on the following pKₐ values, which do you think is more important in determining inductive effects: electronegativity or distance from the reactive acidic hydrogen? Explain in 1–3 complete sentences. **Structures and pKₐ Values:** 1. Structure: A carboxylic acid molecule with a fluorine atom directly attached to the alpha carbon. - pKₐ = 2.68 2. Structure: A carboxylic acid molecule with a fluorine atom attached to the beta carbon. - pKₐ = 3.85 3. Structure: A carboxylic acid molecule with a chlorine atom directly attached to the alpha carbon. - pKₐ = 2.95 4. Structure: A carboxylic acid molecule with a chlorine atom attached to the beta carbon. - pKₐ = 3.97 **Explanation of Inductive Effects:** Inductive effects refer to the electron-withdrawing or electron-donating properties of substituents, affecting the acidity of molecules. The closer an electronegative atom like fluorine or chlorine is to the acidic hydrogen, the stronger the inductive effect is, lowering the pKₐ and therefore increasing acidity. In this example, molecules 1 and 3 (with substituents at the alpha position) have lower pKₐ values compared to molecules 2 and 4 (with substituents at the beta position), indicating that distance has a significant impact on acidity alongside electronegativity.
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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Transcribed Image Text:**Question 6:**
Based on the following pKₐ values, which do you think is more important in determining inductive effects: electronegativity or distance from the reactive acidic hydrogen? Explain in 1–3 complete sentences.
**Structures and pKₐ Values:**
1. Structure: A carboxylic acid molecule with a fluorine atom directly attached to the alpha carbon.
- pKₐ = 2.68
2. Structure: A carboxylic acid molecule with a fluorine atom attached to the beta carbon.
- pKₐ = 3.85
3. Structure: A carboxylic acid molecule with a chlorine atom directly attached to the alpha carbon.
- pKₐ = 2.95
4. Structure: A carboxylic acid molecule with a chlorine atom attached to the beta carbon.
- pKₐ = 3.97
**Explanation of Inductive Effects:**
Inductive effects refer to the electron-withdrawing or electron-donating properties of substituents, affecting the acidity of molecules. The closer an electronegative atom like fluorine or chlorine is to the acidic hydrogen, the stronger the inductive effect is, lowering the pKₐ and therefore increasing acidity. In this example, molecules 1 and 3 (with substituents at the alpha position) have lower pKₐ values compared to molecules 2 and 4 (with substituents at the beta position), indicating that distance has a significant impact on acidity alongside electronegativity.
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