O-Chem: Alkene Reaction with HBr and Methanol

[TrueStar]

Homework Statement

What are the two final products when cis-2-butene reacts with HBr and CH3OH?

Homework Equations

Reactions of Alkenes.

The Attempt at a Solution

I'm not sure if the HBr will attack the double bond first or if the OH on methane will take the H off HBr and create a radical. This sample final I'm working on does not have a key, so there is no way I can check the correct answer and reverse engineer it.

Thank you :)

 

[cep]

Remember there are two products-- what product would each of the options you outlined yield?

 

[TrueStar]

Since there are two secondary carbons, I think I could end up with Bromine on either side of the structure and that the cis-2-butene would be an alkane. I don't know how the methanol plays a part in this though. It's not a peroxide.