Organic Chemistry Question about Solvents

[questioneverything3.14]

Hi! Let's say that you have a hydroxy group, and you covert it to OTos by using TosCl and pyridine. Then, you add a nucleophile to the solution to replace the OTos group. So, I have seen LiBr in acetone as the added nucleophile (specifically, the Br-). However, what about KCl, NaCl, KI, NaI...Is it safe to use acetone as the solvent?

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[laczlacylaci]

Yes, acetone would be safe. Though it is recommended to focus more on the nucleophile in this case, than the solvent! 🙂

 

[questioneverything3.14]

Yes, acetone would be safe. Though it is recommended to focus more on the nucleophile in this case, than the solvent! 🙂

Thank you! Yes, I can never figure out the solvents...some weird ones like DMSO I always forget.

 

[BerkReviewTeach]

DMSO is essentially acetone with an S in the middle instead of C.