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Assume that in a certain H NMR spectrum you find two peaks ofroughly equal inten

ID: 690015 • Letter: A

Question

Assume that in a certain H NMR spectrum you find two peaks ofroughly equal intensity. You are not certain whether these twopeaks are singlets arising from uncoupled protons at differentchemical shifts or are two peaks of a doublet that arise fromprotons coupling with a single adjacent proton. What simpleexperiment could you do perform to distinguish between these twopossibilities?
(this is question 9.33 in Chang's Organic Chemistry 9thedition)
(this is question 9.33 in Chang's Organic Chemistry 9thedition)

Explanation / Answer

A mass spectroscopy or an IR spectroscopy could help; the former because you might be able to get a rough estimate of what compounds are in the molecule, the latter because knowing functional groups can help with determining chemical shift values.