Organic Chemistry (8th Edition)

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

Chapter 21 - Carboxylic Acid Derivatives - Problems - Page 992: Problem 21-2

Answer

The Aldhyde Stretch in IR will appear as two peaks at 2700 and 2800 $cm^{-1}$ plus the carbonyl stretch around 1725 $cm^{-1}$. The Carboxylic Acid stretch appear as Broad Stretch from 2500 to 3500 $cm^{-1}$ Plus the carbonyl stretch around 1710 $cm^{-1}$.

Work Step by Step

Simply 1- if Aldhyde instead of ester it will give us stretches at 1725 $cm^{-1}$ as in the spectrum with us, but will not give us the saturated C-H stretch just before the 3000 $cm^{-1}$ and will give us stretches of aldhyde at 2700 $cm^{-1}$ and 2800 $cm^{-1}$ (two peaks there). 2- And If there is Carboxylic Acid it will give us the Carbonyl stretch as usual, plus the broad stretch from 2500 to 3500 $cm^{-1}$ of the hydroxyl group (-OH). So we can rule out the presence of Aldhyde and Carboxylic acid easily.
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