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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: hairygorillaz on May 09, 2020, 06:02:21 AM

Title: Would 1-Bromoethanol Undergo Iodoform Reaction
Post by: hairygorillaz on May 09, 2020, 06:02:21 AM

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!

Title: Re: Would 1-Bromoethanol Undergo Iodoform Reaction
Post by: chenbeier on May 09, 2020, 06:13:40 AM

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

Title: Re: Would 1-Bromoethanol Undergo Iodoform Reaction
Post by: sjb on May 09, 2020, 08:32:02 AM

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

Title: Re: Would 1-Bromoethanol Undergo Iodoform Reaction
Post by: chenbeier on May 09, 2020, 09:47:36 AM

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.

Title: Re: Would 1-Bromoethanol Undergo Iodoform Reaction
Post by: rolnor on May 09, 2020, 10:46:32 AM

Its a interesting reaction;

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