[hairygorillaz]

Hi guys,

I have a question about 1-bromoethanol and whether it will undergo the iodoform reaction. I have two possible reaction pathways. (1) Oxidation to the acyl bromide, followed by hydrolysis and deprotonation to form an acetate anion. Or (2) Nucleophilic substitution of the bromide, forming a geminal diol, forming acetaldehyde upon losing water which then undergoes the iodoform reaction.

I'm more inclined for (1). Any thoughts? Thanks!

[chenbeier]

I think it will, because also Bromine or Chlorine unter go this reaction. Probably you get a Bromine- diiodinemethan as Product.

[sjb]

I think 1-bromoethanol is quite unstable and will probably decompose to HBr and acetaldehyde / ethanal fairly quickly and probably won't get a chance to undergo the steps you've outlined

[chenbeier]

Oh yes,  I over read the 1. I was thinking 2-Bromoethanol. But even 1-Bromoethanol is meant it will go as you described to acetaldehyd and this will do the Iodoform reaction.

[rolnor]

Its a interesting reaction;

https://en.wikipedia.org/wiki/Haloform_reaction