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Which compound in each of the following pairs is the stronger acid? + + (a) NH N. H2 I or II (b) O2N -NH3" H3C- -NH

Which compound in each of the following pairs is the stronger acid? + + (a) NH N. H2 I or II (b) O2N -NH3" H3C- -NH

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
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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**Comparing Acidic Strength in Compound Pairs** In evaluating the stronger acid from each pair of compounds, consider both structural features and electronic effects that influence acidity. **Pair (a):** - **Compound I**: Ethyl ammonium ion, depicted as \(\text{C}_2\text{H}_5\text{NH}_3^+\). - **Compound II**: Ethyl ammonium ion with an additional methyl group, depicted as \(\text{C}_2\text{H}_5\text{NH}_2^+\). In pair (a), we compare the acidity of two ammonium ions. The presence of an additional alkyl group can influence the electron-donating effect and potentially decrease acidity. **Pair (b):** - **Compound I**: Nitroanilinium ion, depicted as \(\text{O}_2\text{N}-\text{C}_6\text{H}_4-\text{NH}_3^+\). - **Compound II**: Methyl anilinium ion, depicted as \(\text{CH}_3-\text{C}_6\text{H}_4-\text{NH}_3^+\). In pair (b), the nitro group in Compound I is a strong electron-withdrawing group, which can enhance acidity by stabilizing the negative charge in the conjugate base more effectively than the methyl group in Compound II. **Conclusion** Analyzing the electronic effects, substituents that withdraw electrons tend to increase acidity by stabilizing the conjugate base, while electron-donating groups may decrease acidity.
Transcribed Image Text:**Comparing Acidic Strength in Compound Pairs** In evaluating the stronger acid from each pair of compounds, consider both structural features and electronic effects that influence acidity. **Pair (a):** - **Compound I**: Ethyl ammonium ion, depicted as \(\text{C}_2\text{H}_5\text{NH}_3^+\). - **Compound II**: Ethyl ammonium ion with an additional methyl group, depicted as \(\text{C}_2\text{H}_5\text{NH}_2^+\). In pair (a), we compare the acidity of two ammonium ions. The presence of an additional alkyl group can influence the electron-donating effect and potentially decrease acidity. **Pair (b):** - **Compound I**: Nitroanilinium ion, depicted as \(\text{O}_2\text{N}-\text{C}_6\text{H}_4-\text{NH}_3^+\). - **Compound II**: Methyl anilinium ion, depicted as \(\text{CH}_3-\text{C}_6\text{H}_4-\text{NH}_3^+\). In pair (b), the nitro group in Compound I is a strong electron-withdrawing group, which can enhance acidity by stabilizing the negative charge in the conjugate base more effectively than the methyl group in Compound II. **Conclusion** Analyzing the electronic effects, substituents that withdraw electrons tend to increase acidity by stabilizing the conjugate base, while electron-donating groups may decrease acidity.
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