[Ciubba]

My book lists the following reaction: +Br₂, all in a methanol solvent

I'm not sure I understand the product. Wouldn't be a more likely product? If there are no acids involved, I don't see that methanol could act as an electrophile, so one of the bromine must be an electrophile. Then, either the bromide ion or methanol could act as a nucleophile for the newly formed R-bromonium complex, with methanol being more likely as its present in larger concentrations.

[kriggy]

The 1st step is addition of bromine to the double bond forming dibromo compound and then the bromines undergo nucleophilic substitution with methanol

[orgopete]

The 1st step is addition of bromine to the double bond forming dibromo compound and then the bromines undergo nucleophilic substitution with methanol

Although some dibromide may form, I doubt the product is produced from it. I also think the product or products will vary with the reaction conditions under which it is carried out. Additions of bromine to alkenes is quite facile and I think the addition should occur at a faster rate than solvolysis of the bromo ether intermediate. I would write this as a reaction that occurs over two steps, perhaps as producing a kinetic product and a thermodynamic product.

I am going to assume the intermediate bromo ether can be isolated and this reaction is the commercial,source of it. I will guess that solvolysis of this bromide can give the product being noted.

[mjc123]

Yes, but what about the rearrangement (isobut-  n-but-)? Assuming the molecules have been drawn correctly.

[orgopete]

What is the "kinetic" product of this reaction? How might this product rearrange? Hint, pinacol-like.