trihalide/haloform

[stratosphere]

how do the rates of chlorination of a ethanal vs hydrolysis of a trichloroethal compare?

the reason i ask is i was wondering if by using OH- as the limiting reagent(3mols OH- for every mol ethanl) if it would be possible to produce the trichloroethanl as opposed to the chloroform-formic acid products.

[moo]

Maybe oxidizing/chlorinating ethanol with hypochlorite in acidic conditions, in contrast to basic conditions necessary for haloform reaction to work, might do the trick. If you remember, hypochlorite decomposes to chlorine in acidic conditions, and the HOCl also produced is known to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.

[stratosphere]

in acidic conditions aldehydes only get one alpha halogen.

perhaps free radical conditions would work though.
i doubt the trichloro-ethanal would oxidize to trichloroethanoic acid chloride, especially if you did not use an excess of Cl2.