Another Qvault OC Question...

[hope_to_match]

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I am a little confused by how they were able to get the product. I mean I chose that answer because it made sense the most but Br is a better leaving group than Cl is, so why would it replace Cl? Am I over thinking this?

 

[Jordwin]

I am a little confused by how they were able to get the product. I mean I chose that answer because it made sense the most but Br is a better leaving group than Cl is, so why would it replace Cl? Am I over thinking this?

That reagent is tosyl chloride and is a very good leaving group. Good question tho it's tricky

 

[hope_to_match]

ohh grrr i get it now. too bad i didnt recognize that it represents TsCl..! thanks

 

[FeralisExtremum]

I could be wrong, but I'm not seeing Tosyl Chloride anywhere in that reaction...did you mean thionyl chloride?

 

[hope_to_match]

I could be wrong, but I'm not seeing Tosyl Chloride anywhere in that reaction...

its the one after the plus sign with SoCl2 group (the 'real' TsCl has Ch3 instead of NO2) so i guess the react the same

 

[FeralisExtremum]

its the one after the plus sign with SoCl2 group (the 'real' TsCl has Ch3 instead of NO2) so i guess the react the same

Tosyl chloride has two O's and one Cl on the Sulfur group though. SO2Cl vs SOCl2

 

[hope_to_match]

Tosyl chloride has two O's and one Cl on the Sulfur group though. SO2Cl vs SOCl2

ohh you are right! I guess it looks similar so it reacts similar? i dont see any other reason why it would form this product unless it's assumed that this is a similar protecting group as TsCl

 

[FeralisExtremum]

From what I can tell it acts very similar to Tosyl chloride, so reaction-wise it's probably close enough.