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d. Benzylic acid vs. acetic acid HO. pKa = 4.2 4.75

d. Benzylic acid vs. acetic acid HO. pKa = 4.2 4.75

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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Explain the following differences in pKa

**Comparison of Acidities: Molecular Structures and pKa Values** **d. Benzylic acid vs. Acetic acid** - **Benzylic Acid**: This molecule consists of a benzene ring attached to a carboxylic acid group (COOH). The pKa value for benzylic acid is 4.2. - **Acetic Acid**: This molecule has a simple structure with a methyl group attached to a carboxylic acid group. The pKa value for acetic acid is 4.75. - **Summary**: Benzylic acid is slightly more acidic than acetic acid. **e. Methylcyclohexane vs. Toluene** - **Methylcyclohexane**: This molecule features a six-membered cycloalkane ring with a single methyl group. Its pKa value is 50. - **Toluene**: This molecule consists of a benzene ring with a methyl group (CH₃) attached. The pKa value for toluene is 41. - **Summary**: Toluene is more acidic than methylcyclohexane. **f. Cyclopentadiene vs. 1,4-Pentadiene** - **Cyclopentadiene**: This molecule is a five-membered ring with two conjugated double bonds and one hydrogen atom. The pKa value is 16. - **1,4-Pentadiene**: This molecule is a linear structure with two double bonds separated by two single bonds. Its pKa value is 43. - **Summary**: Cyclopentadiene is significantly more acidic than 1,4-pentadiene. These comparisons illustrate how molecular structure impacts acidity, as indicated by pKa values. Lower pKa values denote stronger acids.
Transcribed Image Text:**Comparison of Acidities: Molecular Structures and pKa Values** **d. Benzylic acid vs. Acetic acid** - **Benzylic Acid**: This molecule consists of a benzene ring attached to a carboxylic acid group (COOH). The pKa value for benzylic acid is 4.2. - **Acetic Acid**: This molecule has a simple structure with a methyl group attached to a carboxylic acid group. The pKa value for acetic acid is 4.75. - **Summary**: Benzylic acid is slightly more acidic than acetic acid. **e. Methylcyclohexane vs. Toluene** - **Methylcyclohexane**: This molecule features a six-membered cycloalkane ring with a single methyl group. Its pKa value is 50. - **Toluene**: This molecule consists of a benzene ring with a methyl group (CH₃) attached. The pKa value for toluene is 41. - **Summary**: Toluene is more acidic than methylcyclohexane. **f. Cyclopentadiene vs. 1,4-Pentadiene** - **Cyclopentadiene**: This molecule is a five-membered ring with two conjugated double bonds and one hydrogen atom. The pKa value is 16. - **1,4-Pentadiene**: This molecule is a linear structure with two double bonds separated by two single bonds. Its pKa value is 43. - **Summary**: Cyclopentadiene is significantly more acidic than 1,4-pentadiene. These comparisons illustrate how molecular structure impacts acidity, as indicated by pKa values. Lower pKa values denote stronger acids.
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