Chloral hydrate, or 2,2,2-trichloroethane-1,1-diol to the IUPAC confessor, is a controversial little chemical, in at least three different ways that I can think of right now.

chloral hydrate

I am pretty sure Justus von Liebig did not see it coming, the day he first prepared it in 1832. (Note to the layman: Justus is to organic chemistry, what Elvis is to rock and roll.)

Firstly, the structure is upsetting to organic chemists, because geminal diols are not supposed to be stable. But this one is. On the bright side, this gives us the opportunity to mumble “hyperconjugation“. (Note to the layman: the typical organic chemist has no idea what hyperconjugation really means, but it sounds awesome and helps us excuse a couple of anomalies.)

Secondly, lonely girls in nightclubs should fear chloral hydrate, because it is the magic ingredient in knock-out drops. (Note to the layman: work on your pick-up lines instead.)

Thirdly, perhaps the most debated Nobel Prize ever – the 1948 Physiology or Medicine Award (not even in Chemistry!) “for the discovery of the high efficiency of DDT as a contact poison against several arthropods” – should concern all of mankind, especially since the release of Silent Spring in 1962. (Note to the layman: DDT is a potent but toxic pesticide. It is made from chlorobenzene, a dash of sulfuric acid and – chloral hydrate.)


6 Responses to Chloral hydrate — A feisty little bugger

  1. CatalysisAlex says:

    Oh boy, you got me all teary eyed when I read hyperconjugation….
    Just imagine the discussions one could have at certain places if people remembered…..
    Sorry, just move along, there is nothing to see here.

  2. milkshake says:

    Chloral hydrate is great form making isatins. For a date rape gamma hydroxybutyrate or Rohypnol are the preferred choices (chloral hydrate has a pleasant but fairly strong and characteristic odor and a burning/tingling taste. It has to be given in rather large doses). A funny-tasting drink will give the game away – One might as well use the speedy pick up line: “Does this rag smell like chloroform to you?”

  3. former process chemist says:

    I never knew DDT was a mixture, interesting..

  4. milkshake says:

    commonly-used DDT is actually a mixture of isomers, containing up to 20% of the ortho, para-isomer. These isomeric impurities are not removed because they have similar potency as insecticide as the pure para, para isomer. However they differ significantly in the hormonal-disruptive effects of their main metabolites. The des-chloro metabolite of ortho, para-DDT has been actually developed as adrenal gland suppressor under name Mitoxane. This drug it is given to patients with late-stage metastatic cancer, to block the production of corticosteroids

  5. milkshake says:

    o,p-DDD drug is called Mitotane, sorry for typo

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