Tautomerization Memes

The chemical equivalent of ghosting someone. One minute you're an ynol with your hydroxyl group happily attached, then a proton comes along and suddenly you're a ketene with your oxygen on the complete opposite end. Chemistry's version of "it's not you, it's me" followed by completely rearranging your molecular structure. Organic chemists spend years trying to stabilize these relationships only for H + to slide into DMs and ruin everything.

Organic chemistry professors take tautomerization very seriously. Skip that critical step in alkyne hydration and they'll look at you like you've just claimed water isn't polar. The unstable alcohol intermediate rearranges faster than a grad student clearing their bench when free pizza arrives. Not showing this mechanism step is basically a criminal offense in the organic chemistry world. Some professors still have nightmares about students drawing straight-to-ketone reactions.