Answered: The carbonyl stretch for caffeic acid…

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter15: Carboxylic Acids And Esters

Section: Chapter Questions

Problem 15.66E

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Question

Keeping with the theme of autumn, one of Dr. Danahy’s favorite molecules is caffeic acid due to its presence in pumpkins. This structure serves as an antioxidant and is one of many found within pumpkins. Despite its name, it bears no resemblance to caffeine. Answer the following questions about caffeic acid.

The carbonyl stretch for caffeic acid is unusually low for a carboxylic acid at 1646 cm-1. For reference, the carbonyl stretch for propanoic acid is 1716 cm-1. Explain why the carbonyl stretch occurs at a lower wavenumber for caffeic acid.

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