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 4:**
Explain why the pKa values of the indicated hydrogen atoms change as they do for these three compounds.
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**Diagram Explanation:**
The image shows three different organic compounds. Each compound has a hydrogen atom indicated, and its respective pKa value is provided.
1. **Compound 1:**
- Structure: Alkane with a simple carbon chain
- Indicated Hydrogen: Attached to a carbon in the chain
- pKa = 50
2. **Compound 2:**
- Structure: Ketone (carbonyl group present)
- Indicated Hydrogen: Attached to a carbon adjacent to the carbonyl group
- pKa = 20
3. **Compound 3:**
- Structure: 1,3-Dicarbonyl compound (two carbonyl groups present)
- Indicated Hydrogen: Attached to a carbon between the two carbonyl groups
- pKa = 10
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**Analysis:**
The decreasing pKa values reflect increasing acidity of the hydrogen atoms in the compounds. The differences arise due to the following reasons:
- **Inductive Effect:** The presence of electronegative atoms or groups (such as the carbonyl groups) pulls electron density away from the hydrogen, stabilizing the negative charge that results when the hydrogen ionizes.
- **Resonance Stabilization:** In compound 3, the ionized form of the hydrogen is stabilized by resonance between the two carbonyl groups, significantly lowering the pKa compared to compound 2.
- **Hybridization:** The hybridization of the carbon atom to which hydrogen is attached also affects acidity, with more s-character leading to stronger acids.
This detailed exploration helps students understand how structural features influence acidity in organic molecules.
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