Dicarboxylic acids have two pKa's. For maleic acid (cis-2-butenedioic acid) these are pka¹ = 2.0, and pKå² = 6.3 For fumaric acid (trans-2-butenedioic acid) these are pK₂¹ = 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 O d. Intramolecular hydrogen bonding
Dicarboxylic acids have two pKa's. For maleic acid (cis-2-butenedioic acid) these are pka¹ = 2.0, and pKå² = 6.3 For fumaric acid (trans-2-butenedioic acid) these are pK₂¹ = 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 O d. Intramolecular hydrogen bonding
Chapter20: Carboxylic Acids And Nitriles
Section20.4: Substituent Effects On Acidity
Problem 7P: Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a...
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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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe7149786-a633-455d-90e0-b7ec6ba41ada%2F0011eeec-9943-4f70-8613-30b8fe340708%2Ftqtnno_processed.png&w=3840&q=75)
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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