
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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![Use the information in the \( pK_a \) table to rank the molecules in order of increasing basicity. For example, select "1" in the second column for the weakest base and "2" for the next weakest base and so on.
**Table: Molecules**
- Cl\(^-\) [(Choose one) ▼]
- CH\(_3\)NH\(^-\) [(Choose one) ▼]
- NH\(_3\) [(Choose one) ▼]
- HSO\(_4^-\) [(Choose one) ▼]
**\( pK_a \) table:**
- CH\(_4\): 48
- NH\(_3\): 38
- H\(_2\): 36
- CH\(_3\)NH\(_2\): 33
- H\(_2\)O: 15.7
- CH\(_3\)OH: 15.5
- CH\(_3\)NH\(_3^+\): 10.6
- CH\(_3\)SH: 10.4
- HCN: 9.4
- NH\(_4^+\): 9.2
- H\(_2\)S: 7.00
- CH\(_3\)CO\(_2\)H: 4.76
- HF: 3.17
- H\(_3\)O\(^+\): -1.7
- CH\(_3\)OH\(_2^+\): -2.2
- H\(_2\)SO\(_4\): -3.0
- HCl: -7
- HBr: -9](https://content.bartleby.com/qna-images/question/70c6702f-1254-4f2b-ba5a-ac93276291c3/d30cdccd-0ce4-48fc-9599-8655c98824df/x0hh9w5_thumbnail.jpeg)
Transcribed Image Text:Use the information in the \( pK_a \) table to rank the molecules in order of increasing basicity. For example, select "1" in the second column for the weakest base and "2" for the next weakest base and so on.
**Table: Molecules**
- Cl\(^-\) [(Choose one) ▼]
- CH\(_3\)NH\(^-\) [(Choose one) ▼]
- NH\(_3\) [(Choose one) ▼]
- HSO\(_4^-\) [(Choose one) ▼]
**\( pK_a \) table:**
- CH\(_4\): 48
- NH\(_3\): 38
- H\(_2\): 36
- CH\(_3\)NH\(_2\): 33
- H\(_2\)O: 15.7
- CH\(_3\)OH: 15.5
- CH\(_3\)NH\(_3^+\): 10.6
- CH\(_3\)SH: 10.4
- HCN: 9.4
- NH\(_4^+\): 9.2
- H\(_2\)S: 7.00
- CH\(_3\)CO\(_2\)H: 4.76
- HF: 3.17
- H\(_3\)O\(^+\): -1.7
- CH\(_3\)OH\(_2^+\): -2.2
- H\(_2\)SO\(_4\): -3.0
- HCl: -7
- HBr: -9

Transcribed Image Text:**Title: Determining Acidity of Highlighted Hydrogen Atoms in Organic Molecules**
---
**Instructions:**
In each row, select the molecule with the highlighted hydrogen (H) atom that is more acidic.
---
### Row 1:
- **Molecule 1:** Features a sulfur atom attached to a carbon-hydrogen chain. The highlighted hydrogen is bonded directly to a sulfur (SH).
- **Molecule 2:** Shows a similar carbon-hydrogen chain with sulfur, but the highlighted hydrogen is not directly bonded to sulfur.
**Selection:**
- The first molecule has the more acidic hydrogen atom, indicated by a checkmark circle.
### Row 2:
- **Molecule 1:** Contains a nitrogen atom bonded within the carbon chain. The highlighted hydrogen is on a nitrogen (NH).
- **Molecule 2:** Shows the highlighted hydrogen bonded to a nitrogen within a similar carbon structure.
**Selection:**
- No selection is indicated for either molecule.
### Row 3:
- **Molecule 1:** A cyclic structure with a sulfur atom. The highlighted hydrogen is bonded to a carbon in the ring.
- **Molecule 2:** A similar cyclic structure with sulfur, but the highlighted hydrogen is directly bonded to sulfur (SH).
**Selection:**
- No selection is indicated for either molecule.
### Row 4:
- **Molecule 1:** Linear carbon-hydrogen chain with the highlighted hydrogen on an end carbon.
- **Molecule 2:** Similar linear chain, but with the highlighted hydrogen closer to an oxygen atom (OH).
**Selection:**
- No selection is indicated for either molecule.
---
**Conclusion:**
The acidity of hydrogen atoms in organic molecules can vary significantly depending on the surrounding atoms and the functional group to which they are attached. Typically, hydrogen atoms bonded to electronegative elements or groups capable of stabilizing the negative charge are more acidic.
This exercise aims to enhance the understanding of how molecular structure impacts acidity, crucial for predicting reactivity and behavior in chemical reactions.
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