[clowell]

Convert 1-methylcyclohexanol to 1-bromo-2-methylcyclohexane.

Should I use HBr and peroxides?

[kp2171]

This is an older post so probably too late for a test, though something that would be on midterm or final so here's the answer.

You'd be fine using HBr with peroxide, but remember that its used commonly to add across C=C bonds... so you need to dehydrate the alcohol to make an alkene first (H2SO4 and heat commonly, or CH3OH and heat) and then do the addition of the HBr anti markovnikov using HBr and peroxides.