CrimpJiggler - 7-9-2011 at 02:53
Does aqueous HCl react with acetone to form 2-chloro-2-hydroxy-propane? Cl- is quite a strong nucleophile so I assume that it should add to the
carbonyl carbon on in acetone and other non sterically hindered ketones but I can't find any info on hydrohalogenations of ketones. Is there something
I'm not taking into consideration here?
[Edited on 7-9-2011 by CrimpJiggler]
ScienceSquirrel - 7-9-2011 at 05:31
Halide is also a very good leaving group and the competing reaction of eliminating hydrogen chloride is even more favourable than addition.
The major reaction is protonation to form the protonated ketone / enol, if a good electrophile like halogen is present you get alpha halogenation to
form the extremely lacrymatory chloroacetone which is poor man's tear gas! 