Comments on: Thionyl Chloride (SOCl2)

By: James Ashenhurst

James Ashenhurst — Fri, 01 Oct 2021 20:38:32 +0000

In reply to Sarah. If it is a phenol, it will be unreactive towards thionyl chloride since SN2 type reactions are impossible. The acyl halide will be formed instead, however I strongly suggest protecting your phenol group, otherwise you will end up with a mess.

By: Sarah

Sarah — Fri, 01 Oct 2021 15:05:36 +0000

Hi
I have an equestion please
Which is more reactive carboxyl group or hydroxyl group toward thionylchloride (these to functional groups are meta position to each other in certain compound )?I try to synthesis acyl chloride derivarive on carboxyl group , Is that possible in this case ?

By: James Ashenhurst

James Ashenhurst — Thu, 28 May 2020 01:44:11 +0000

This was done awhile ago. I would recommend protonation deprotonation as two separate steps now. Past introductory organic chemistry, we often just say “proton transfer” and be done with it, like waving a magic wand.

By: James Ashenhurst

James Ashenhurst — Thu, 28 May 2020 01:42:38 +0000

Chloride ion can be an OK base. It’s competent to to the deprotonation to restore aromaticity in electrophilic aromatic substitution reactions. Some counterions aren’t basic enough to do this (e.g. triflate).

By: Yves de Montaudouin

Yves de Montaudouin — Tue, 26 May 2020 22:36:21 +0000

By the way your table of 9 or 10 carbonyl mechanism is absolutely fantastic. It was a great idea to have this PT step instead of a protonation-deprotonation.
But aren’t some teacher going to complain about this internal reaction?

By: Yves de Montaudouin

Yves de Montaudouin — Tue, 26 May 2020 22:32:12 +0000

Last step:
I have never seen a Cl- deprotonate anything. Maybe we should have H20 do it.

By: shrajan

shrajan — Mon, 27 Jan 2020 03:06:25 +0000

Thanks your stuff is really helpful.Also i am from India

By: James Ashenhurst

James Ashenhurst — Wed, 28 Aug 2019 02:28:10 +0000

In reply to Aoife Reynolds. I can't really visualize the question. Could you attach an imgur or equivalent?

By: Aoife Reynolds

Aoife Reynolds — Mon, 22 Jul 2019 16:51:04 +0000

What about if you have both an alcohol and carboxylic acid in the molecule and both are chlorinated? With an imidazole present, is it acting as a base to deprotonate the carboxylic hydroxyl or is it acting as a solvent?

By: James Ashenhurst

James Ashenhurst — Tue, 16 Apr 2019 08:04:24 +0000

In reply to Rico.

Thank you. In response to your comment, I spent about ten hours writing this post. See this: https://www.masterorganicchemistry.com/2014/02/10/socl2-and-the-sni-mechanism/