Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 20 - Carboxylic Acids - Problems - Page 954: Problem 20-8 c

Answer

The OH group proton in case of propan-1-ol shows peak around 4.7 ppm, while it is shifted to around 11.0 ppm in case of propanoic acid. The CH2 group splitting next to OH group of aldehyde is absent in the spectrum of propanoic acid, as the protons are removed due to oxidation.

Work Step by Step

The shifting of OH proton in case of propanoic acid compare to propan-1-ol is due to deshielding effect as COOH is electron withdrawing group, which is attributed to the electron withdrawing nature of C=O group. The figure contains the spectrum of propan-1-ol (A) and propanoic acid (B) as inlet figure.
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