The pKa of phenol is 10.0 and the pKa of para-nitrophenol is 7.2. Given this information, one knows that The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol Both acids are bases

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**Understanding Acidity and Stability in Organic Compounds**

The __p__K<sub>a</sub> of phenol is 10.0 and the __p__K<sub>a</sub> of para-nitrophenol is 7.2. Given this information, one knows that:

1. ☐ The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol.
2. ☐ The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol.
3. ☐ The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol.
4. ☐ Both acids are bases.

**Explanation:**
The __p__K<sub>a</sub> value is a measure of acidity; the lower the __p__K<sub>a</sub>, the stronger the acid. A __p__K<sub>a</sub> of 7.2 for para-nitrophenol indicates that it is a stronger acid compared to phenol, which has a __p__K<sub>a</sub> of 10.0.

- **Option 1:** This statement is incorrect because a stronger acid (lower __p__K<sub>a</sub>) has a more stable conjugate base.
- **Option 2:** This statement is incorrect because the stability of the conjugate base is in question, not the conjugate acid.
- **Option 3:** This is the correct statement. The lower __p__K<sub>a</sub> of para-nitrophenol suggests that its conjugate base is more stable than that of phenol.
- **Option 4:** This statement is incorrect as it suggests that acids can act as bases, which they typically do not as they are proton donors.

In summary, the correct conclusion is:

**The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol.**
Transcribed Image Text:**Understanding Acidity and Stability in Organic Compounds** The __p__K<sub>a</sub> of phenol is 10.0 and the __p__K<sub>a</sub> of para-nitrophenol is 7.2. Given this information, one knows that: 1. ☐ The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol. 2. ☐ The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol. 3. ☐ The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol. 4. ☐ Both acids are bases. **Explanation:** The __p__K<sub>a</sub> value is a measure of acidity; the lower the __p__K<sub>a</sub>, the stronger the acid. A __p__K<sub>a</sub> of 7.2 for para-nitrophenol indicates that it is a stronger acid compared to phenol, which has a __p__K<sub>a</sub> of 10.0. - **Option 1:** This statement is incorrect because a stronger acid (lower __p__K<sub>a</sub>) has a more stable conjugate base. - **Option 2:** This statement is incorrect because the stability of the conjugate base is in question, not the conjugate acid. - **Option 3:** This is the correct statement. The lower __p__K<sub>a</sub> of para-nitrophenol suggests that its conjugate base is more stable than that of phenol. - **Option 4:** This statement is incorrect as it suggests that acids can act as bases, which they typically do not as they are proton donors. In summary, the correct conclusion is: **The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol.**
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