Theory suggests that the
experiment should work. However, the only
precedent you find is either a)
in another language b) from 1927 c)
has no experimental explanation or d)
was published by a group nobody knows about and has never been cited.
It's 9 PM. None of your glassware is clean.
You can't decide what scale to run it on
and you don't have any of the reagents.
You need to weigh four different reagents: a hygroscopic solid that
gets liquidy in the air, 0.05 mg of catalyst, a liquid that clogs
syringes and must be distilled immediately before use, and your
precious reactant, which is heat and acid sensitive. The reaction
must be done at -30oC under argon using a complex glass apparatus,
and requires three flasks for successive dropwise addition via
cannula.
The reaction takes hours to complete: however, the product is unstable
and decomposes slowly under the reaction conditions. Progress cannot
be monitored by TLC.
The product mixture is highly reactive and requires dropwise addition
of quenching reagent to prevent a volcano-like exothermic eruption.
A number of nightmares are possible at this point:
Upon combination of organic and aqueous solutions gives a gooey or
insoluble precipitate is present, which floats between the two layers
and obscures the border.
When an aqueous solvent is added to the diluted reaction mixture, an
emulsion forms. All efforts to resolve the layers fail, your solution
has swollen to gargantuan proportions, and you can't find or can't
lift a separatory funnel large enough to hold it.
During Acid/Base Workup, the expected precipitate does not form.
Upon addition of aqueous bicarbonate, the organic layer
becomes a graceful fountain, coating the inside of your fume hood.
Addition of aqueous solution to your black organic
reaction mixture leads to a uniform black mixture.
The aqueous solution you use to wash the organic
layer turns yellow, orange, brown or pink-
the first ten times you try it.
Your compound is an oil. No purification method has
been reported for its isolation. The crude reaction mixture
has three or four isomeric components, all with similar
boiling points and Rf values.
All of the peaks in your 1H NMR spectrum overlap,
the compound is not the one you expected, and you don't know what it is.
It's time to write your thesis. You find that
characterization data is missing, and need to repeat
some experiments you ran earlier. Your notebook is not
very detailed, and you have trouble reproducing the results,
and have to work out the experimental conditions and a
purification protocol all over again.