[faust]

Hello,

this is an exercice where we hydrolyze two tosylate. I think there is a neighbouring group participation from the tosyle in one case in order to produce one enantiomere.

And in the second case, we have a SN1. But how could you explain, in that case, why we don't have the neighbouring group participation from the aromatic?

Thank you

[Dan]

Does this argument look sensible to you guys?

*updated*

[faust]

Thank you that's the answer I think!

[Dan]

Hang on! It's not sterics, I thought that was a dodgy argument! If you look at the bridged intermediate from the first one, attach by water can occur on either carbon, so the product is racemic.

Same for the second, but both lead to the same product. I will update the scheme in my previous post!