When an NMR spectrum is taken of the molecule below, there is the expected 5H in the aromatic region, triplet (3H) and quartet (2H) upfield of the aromatic region. After adding a drop of acidic D2O, the spectrum changes to one that just has 5H aromatic protons and an upfield 3H singlet. What happens? Explain with mechanisms step by step and include charges and lone pairs of all compounds involved.

When an NMR spectrum is taken of the molecule below, there is the expected 5H in the aromatic region, triplet (3H) and quartet (2H) upfield of the aromatic region. After adding a drop of acidic D2O, the spectrum changes to one that just has 5H aromatic protons and an upfield 3H singlet. What happens? Explain with mechanisms step by step and include charges and lone pairs of all compounds involved.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 49AP: The infrared spectrum of the compound with the mass spectrum shown below has a medium-intensity peak...

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