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.

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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. 

 

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