Halogenation of 4‐methylcyclohex‐1‐ene

My problem is with the methyl group. If it wasn't there, I had no problem. When the halonium bridge is made does the methyl group shift to give a more stable transition state or not?

• I would believe that Br is attached mostly on the Carbon 4, and Br or OH on the Carbon 3. – Maurice Dec 27 '19 at 13:15
• Why? I would expect a mixture close to 1:1 – Waylander Dec 27 '19 at 13:19

methyl groups will not shift in a non-classical carbocation mechanism. This reaction will first have a $$TS$$ where the $$\ce{Br2}$$ molecule makes a 3 membered ring with the $$\pi%$$ bond and the water molecule will attach itself to $$\ce{C3}$$, as that is a more stable electron-deficient site due to the inductive effect of the methyl group.