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4. Explain why the pka values of the indicated hydrogen atoms change as they do for these three compounds jh fl f pka 10 pka-10 Ka-20

4. Explain why the pka values of the indicated hydrogen atoms change as they do for these three compounds jh fl f pka 10 pka-10 Ka-20

Chemistry
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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Question 4:** Explain why the pKa values of the indicated hydrogen atoms change as they do for these three compounds. --- **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 --- **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.
Transcribed Image Text:**Question 4:** Explain why the pKa values of the indicated hydrogen atoms change as they do for these three compounds. --- **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 --- **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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