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

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...
icon
Related questions
Question
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
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
Expert Solution
steps

Step by step

Solved in 2 steps

Blurred answer
Knowledge Booster
Spectroanalytical Methods
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY