Sciencemadness Discussion Board

Reaction of formyl bromide with isopropenyl alcohol?

ScienceSquirrel - 7-5-2013 at 03:30

http://www.chemsink.com/reaction/348863/

Nicodem - 7-5-2013 at 08:21

Idiocy like that is more common than what one would hope. I have seen professors giving out problems involving reactions with formyl chloride at the university level, so I'm not surprised. This one is actually even more funny. Not only it gives a reaction that involves a reactant that does not and cannot exist (HCOBr), but the other reactant has a half-life of about half an hour at room temperature in absolute absence of any trace of acids or bases. Its half-life shortens to seconds in the presence of even slightest trace of acids or bases (isn't HBr a very strong acid?). What's more absurd, even if we ignore the existence/stability of the two reactants, the reaction depicts only one product, or at least insinuates an unlikely selectivity. It is uncertain that the product would be only the isopropenyl formate. There should form also substantial amounts of the 3-oxo-butanal, because the nucleophile is ambident and the electrophile is relatively soft (in the HSAB sense) when compared to acid anhydrides or acyl chlorides.

zed - 8-5-2013 at 18:09

Hey! I once had to sit in a Bio-Chem class, conducted by a Bio-Chem PHD Candidate, wherein it was pronounced that Acetone was the simplest Ester.

Oddly enough, though I knew substantially more about chemistry than the instructor, I was somehow unable to get an A in that class.

Alas, I was a younger man then, and though I hid in the back rows, I was unable to completely control my frequent head shaking. Made him very uneasy, I suppose. Not my fault he didn't know basic O-Chem; that it was just something he once memorized, in route to an advanced degree in Chemistry.

Punished me with a B he did. Not that I gave a crap.


woelen - 14-5-2013 at 04:06

Quote: Originally posted by ScienceSquirrel  
http://www.chemsink.com/reaction/348863/
This is higher chemistry, mixed with advanced physics! It is clear to me that this is about a reaction in a slightly different universe with slightly different atomic properties. Of course formyl bromide is dirt cheap and stable in that universe :P