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Topic: Would 1-Bromoethanol Undergo Iodoform Reaction  (Read 409 times)

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Offline hairygorillaz

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Would 1-Bromoethanol Undergo Iodoform Reaction
« 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!

Offline chenbeier

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Re: Would 1-Bromoethanol Undergo Iodoform Reaction
« Reply #1 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.

Offline sjb

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Re: Would 1-Bromoethanol Undergo Iodoform Reaction
« Reply #2 on: May 09, 2020, 08:32:02 AM »
I think 1-bromoethanol CC(Br)O 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

Offline chenbeier

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Re: Would 1-Bromoethanol Undergo Iodoform Reaction
« Reply #3 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.

Online rolnor

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Re: Would 1-Bromoethanol Undergo Iodoform Reaction
« Reply #4 on: May 09, 2020, 10:46:32 AM »

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