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 over a few minutes to one that just has 5H aromatic protons and an upfield 3H singlet. What happens? Explain with mechanisms. H3C,

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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 over a few minutes to one that just
has 5H aromatic protons and an upfield 3H singlet. What happens? Explain with mechanisms.
H3C.
Transcribed Image Text: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 over a few minutes to one that just has 5H aromatic protons and an upfield 3H singlet. What happens? Explain with mechanisms. H3C.
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