[bhkuk]

hellow
i am making areaction with (-)Menthyl (R)-p-toluenesulfinate with methylmagnesium iodide, the reaction thake place at anhydrous benzene. after doing the reaction i am making hydrolyse with ammonium chloride.
so i have to question about the reaction:
A. why does my solvent is benzene? why not to do it in anhydrous ether?
B. why do i make hydrolise with ammonium chloride? which reaction is accure? what is the mechnism? why not to hydrolise with water?

[trufalup]

A: Only God knows why. Most likely, the nature of your toluenesilfinyl group is more polare and more soluble in benzene than in ether.

B. You need a weak acid to destroy the excess Grignard reagent (also, the Mg coordinated intermediate). If you use a stronger source of protons, like methanol, you run the risk of a highly volatile and exothermic reaction when you gret rid of the Magnesium.