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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Question

Figure A shows a cyclic ketone with the molecular formula C₅H₈O. The α-hydrogen is located on the carbon adjacent to the carbonyl group.
**Compound B:**

Figure B shows a cyclic dione with the molecular formula C₆H₈O₂. The α-hydrogen is located on the carbon adjacent to two carbonyl groups.
Both compounds have their structures represented with equilibrium arrows indicating the deprotonation process:
```
O
/ \
CH2 \
| /
(double arrow showing equilibrium process)
(first compound's equivalent resonance structure(s) - empty box)
```
```
O O
/ \ // \
CH2 \
| /
(double arrow showing first equilibrium process)
(first resonance structure - empty box)
(double arrow showing second equilibrium process)
(second resonance structure - empty box)
```
#### pKa Values
**a)** For Compound A:
```
pKa: (empty box for student input)
```
**b)** For Compound B:
```
pKa: (empty box for student input)
```
#### Discussion
**c)** Explain their difference in pKa:
(Empty line for detailed answer)
The difference in pKa can be attributed to the nature and number of electron-withdrawing groups adjacent to the α-hydrogen. For Compound A, the presence of one carbonyl group impacts the acidity, while for Compound B, the presence of two carbonyl groups significantly increases the withdrawal effect, resulting in a different pKa value.
---
#### Conclusion
This exercise demonstrates the importance of structural features on the acidity of compounds and helps in understanding fundamental concepts of organic chemistry, specifically regarding the electron-withdrawing effects of carbonyl groups on adjacent hydrogens.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F30c2e2f2-e45c-41de-86ef-a25e36084e76%2Fca9fd8dc-0025-4c5f-926d-36e6dca50a87%2Fxja76f.jpeg&w=3840&q=75)
Transcribed Image Text:### Identifying pKa Values of α-Hydrogen in Compounds
#### Introduction
Determining the pKa values of α-hydrogens in various compounds is important in understanding their acidity. Here, we will analyze the pKa values on a scale of 5 of the α-hydrogen in two compounds labeled as A and B, and then explain their differences.
#### Structures and pKa Values
**Compound A:**

Figure A shows a cyclic ketone with the molecular formula C₅H₈O. The α-hydrogen is located on the carbon adjacent to the carbonyl group.
**Compound B:**

Figure B shows a cyclic dione with the molecular formula C₆H₈O₂. The α-hydrogen is located on the carbon adjacent to two carbonyl groups.
Both compounds have their structures represented with equilibrium arrows indicating the deprotonation process:
```
O
/ \
CH2 \
| /
(double arrow showing equilibrium process)
(first compound's equivalent resonance structure(s) - empty box)
```
```
O O
/ \ // \
CH2 \
| /
(double arrow showing first equilibrium process)
(first resonance structure - empty box)
(double arrow showing second equilibrium process)
(second resonance structure - empty box)
```
#### pKa Values
**a)** For Compound A:
```
pKa: (empty box for student input)
```
**b)** For Compound B:
```
pKa: (empty box for student input)
```
#### Discussion
**c)** Explain their difference in pKa:
(Empty line for detailed answer)
The difference in pKa can be attributed to the nature and number of electron-withdrawing groups adjacent to the α-hydrogen. For Compound A, the presence of one carbonyl group impacts the acidity, while for Compound B, the presence of two carbonyl groups significantly increases the withdrawal effect, resulting in a different pKa value.
---
#### Conclusion
This exercise demonstrates the importance of structural features on the acidity of compounds and helps in understanding fundamental concepts of organic chemistry, specifically regarding the electron-withdrawing effects of carbonyl groups on adjacent hydrogens.
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