Question

The mixture of dimethylsulfoxide (DMSO) and hydrobromic acid results in the formation of bromodimethylsulfonium bromide, which can serves as a source of electrophilic bromine.

Draw the complete mechanism to generate the major product. Your mechanism should include: generation of the active halogenating species and the steps to provide the stable product, proper arrows, formal charges, and labels for the rate-determining step. You should also draw all important resonance structures for any reaction intermediate(s).

active brominating species Br Br Br HBr DMSO room temperature 2 h (97% yield) bromodimethylsulfonium bromide

Answer 1

DMSO 2ん 97% γ¡eld) Mechalone 씻 ·tp. → t B O M60 Br Activt byomitig species fr 田田 Step Pret)