Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 3, Problem 68P

Recall from section 1.10B that there is restricted rotation around carbon-carbon double

bonds. Maleic acid and fumaric acid are two isomers with vasity different physical properties and p K a values for loss of both protons. Explain why each of these differences occurs.

Chapter 3, Problem 68P, 3.65 Recall from section 1.10B that there is restricted rotation around carbon-carbon double 
bonds.

maleic acid fumaric acid

mp ( ο C ) 130 solubility ( g/L ) in H 2 O at 25 ο C 788 p K a 1 1.9 p K a 2 6.5 286 7 3.0 4.5

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