Monosaccharides - Aldose-Ketose Rearrangement Video Lessons

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Problem: Compound A can interconvert to different sugars by way of enol-ketone tautomerization. Which sugar (1–5) could not be prepared by a  single enol–ketone tautomerization reaction of A?

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Compound A can interconvert to different sugars by way of enol-ketone tautomerization. Which sugar (1–5) could not be prepared by a  single enol–ketone tautomerization reaction of A?

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Based on our data, we think this problem is relevant for Professor Laude's class at TEXAS.