Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Dicarboxylic acids have two pKa's.
For maleic acid (cis-2-butenedioic acid) these are pKa¹ = 2.0, and pK₂² = 6.3
For fumaric acid (trans-2-butenedioic acid) these are pka¹ = 3.0, and pk₂² = 4.5
Which factor best explains why the cis-isomer has a smaller pK₂¹ and a larger pK₂²
than the trans-isomer?
2
a. Intramolecular dipole repulsion
b. Intramolecular steric hindrance
c. Selective solvation in water
d. Intramolecular hydrogen bonding
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Transcribed Image Text:Dicarboxylic acids have two pKa's. For maleic acid (cis-2-butenedioic acid) these are pKa¹ = 2.0, and pK₂² = 6.3 For fumaric acid (trans-2-butenedioic acid) these are pka¹ = 3.0, and pk₂² = 4.5 Which factor best explains why the cis-isomer has a smaller pK₂¹ and a larger pK₂² than the trans-isomer? 2 a. Intramolecular dipole repulsion b. Intramolecular steric hindrance c. Selective solvation in water d. Intramolecular hydrogen bonding
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