What is this reaction called? What is going on?

[510586]

Would this be some kind of Williamson ether synthesis? No idea

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[DrNutmeg]

After looking at it for 5 secs, I'm thinking aromatic addition? is the answer c?

 

[510586]

It was b ester formation. Thought Williamson needed a Nah

 

[thegreat267]

Correct me if I'm wrong, but this is a sn2 mechanism thats involves a tosylate.

 

[510586]

Correct me if I'm wrong, but this is a sn2 mechanism thats involves a tosylate.

So like Williamson kind of? The end result looks like it

 

[DrNutmeg]

in sn2 with tosylate, shouldn't the tosylate leave? It's like the best leaving group in the game...

 

[510586]

Orgoman will come to the rescue soon lol

 

[LolaSF]

Maybe I'm wrong.. but when I looked at this I saw just the conversion of the OH to a good LG

 

[DAT Destroyer]

View attachment 193553 Would this be some kind of Williamson ether synthesis? No idea

This reaction is the formation of a sulfonate ester. We do this to create a good leaving for a nucleophilic attack. Recall the OH group is not a good leaving group under most circumstances.

This is a substitution type of a mechanism ...think of it as SN2-like.

Hope this helps.

Dr. Romano

 

[100%permwinner]

in sn2 with tosylate, shouldn't the tosylate leave? It's like the best leaving group in the game...

It is a SN2 reaction where the Cl- leaves.

 

[510586]

This reaction is the formation of a sulfonate ester. We do this to create a good leaving for a nucleophilic attack. Recall the OH group is not a good leaving group under most circumstances.

This is a substitution type of a mechanism ...think of it as SN2-like.

Hope this helps.

Dr. Romano

Oh so is this just like the O Ts reactions?

 

[virtualmaster999]

Oh so is this just like the O Ts reactions?

If it makes it easier, picture it like a nucleophilic acyl sub. rxn....acyl chloride with alcohol forms ester....sulfonic ester formed like Dr. Romano stated previously.