Dicarboxylic acids have two pKa's. -  For maleic acid (cis-2-butenedioic acid) these are pKa1 = 2.0, and pKa2 = 6.3 -  For fumaric acid (trans-2-butenedioic acid) these are pKa1 = 3.0, and pKa2 = 4.5 Which factor best explains why the cis-isomer has a smaller pKa1 and a larger pKa2 than the trans-isomer?   a. Intramolecular hydrogen bonding   b. Intramolecular steric hindrance   c. Selective solvation in water   d. Intramolecular dipole repulsion

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
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 pKa2 = 6.3
-  For fumaric acid (trans-2-butenedioic acid) these are pKa1 = 3.0, and pKa2 = 4.5

Which factor best explains why the cis-isomer has a smaller pKa1 and a larger pKa2 than the trans-isomer?

  a.

Intramolecular hydrogen bonding

  b.

Intramolecular steric hindrance

  c.

Selective solvation in water

  d.

Intramolecular dipole repulsion

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