What is the reaction workup that ruined your day?

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Okay, I am a trained organic chemist. I wonder how universal the problem is to other fields, but have you ever heavily invested in a reaction (reaction, time, and hair loss) only to find that you cannot extract your product?

I am asking this question to try to survey difficult tasks in (manual) experimentation, particularly liquid-liquid extraction, and work with colleagues to solve them with new automated equipment and computer vision, etc.

Please post your sad stories here. Please indicate the reaction type, what worked for you, and what did not.

If you prefer privacy, submit your stories here: https://forms.gle/AYPQiUYm3eBW5Aky7.

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One example:
I made a super water-soluble peptide. I tried to extract it with dichloromethane from water but did not get much out. I had to do the extraction many times blindly because the peptide did not have any chromophores for detection using DAD. Later I realized that the pH was too low.
How should I track the compound if it does not have chromophores?

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