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Chemistry

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  • $\begingroup$ I did read that geminal diol stability varies and why (oxygen repulsion). However, I read the exact same reasons for hemiacetal instability. So I figured I should find hard numbers like equilibrium constants. The only source I can find showing equilibrium constants for a wide variety of carbonyl species is a page of lecture notes that cites two old sources, one for hemiacetals and one for hydrates, and it suggests that the more readily an aldehyde reacts with water, the more readily it reacts with methanol. I can't find a single mention of a glucose-geminal-diol, like it didn't exist. $\endgroup$
    – BatWannaBe
    Commented Apr 15, 2019 at 18:32
  • $\begingroup$ You are referring to this source $\endgroup$
    – Karsten ♦
    Commented Apr 15, 2019 at 18:44
  • 1
    $\begingroup$ Yes, exactly. Not great because the methanol is the most similar to water in size and shape of all the alcohols, but it was the only source I could find with both hemiacetal and hydrate reactions for a wide variety of species that wasn't behind a paywall. $\endgroup$
    – BatWannaBe
    Commented Apr 15, 2019 at 18:55
  • $\begingroup$ @BatWannaBe I added two references (still not exactly what you were asking, but relevant). $\endgroup$
    – Karsten ♦
    Commented Apr 15, 2019 at 19:31