Things I Have Done, So You Don’t Have To…
True stories from more than 30 years in chemistry: stubborn reactions, surprising spectra, scale-up lessons, laboratory mishaps and the occasional instrument that appeared to harbour a personal grudge.
Tales from the Bench began as a personal LinkedIn series: practical laboratory stories told with enough chemistry to be useful, and enough hindsight to make them safe to laugh at.
The web editions preserve the original character of the posts while giving each tale more room for the chemistry, diagnosis, context and practical lesson that emerged from it.
Eight expanded stories from the LinkedIn series, covering synthesis, analytical puzzles, scale-up, equipment failure, safety and the occasional argument with artificial intelligence.
A Pummerer reaction appeared to fail for no obvious chemical reason. The culprit was not the route itself, but trace chloride carried forward as sodium chloride.
A successful crystallisation changed behaviour on scale-up and produced a second polymorph. The solution lay in cooling more slowly and adjusting the dilution rather than blaming the compound.
Preparative LC-MS appeared to destroy the purity of a fused-ring compound. A reversible ring-opening process under basic conditions, accompanied by a –14 Da shift, was the real explanation.
A vacuum oven failed overnight and ran beyond 200 °C. The product was carbonised, the bottle distorted and the lesson about unattended equipment arrived in unmistakably blackened form.
One story involved sodium hydride, moisture and a plastic bottle that was never going to win. The other involved a wet acetone-rinsed flask, a hot-air gun and the rapid disappearance of part of an eyebrow.
A sulfonyl chloride reaction on a heterocycle did not reward patience. The chemistry needed timely interruption rather than prolonged attention, proving that “leave it a little longer” is not a universal synthetic strategy.
A disagreement over Turbo-Grignard metalation of 2-(methylthio)-4,6-dichloropyrimidine became a lesson in chemical instinct, mechanistic humility and AI’s ability to defend the wrong answer with extremely convincing prose.
A bottle labelled 1.6 M n-butyllithium had quietly become something closer to half strength: a lesson in reagent age, titration, handling history and the danger of trusting appearances.
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