I'm relatively new to the Chemistry SE community, and sometimes when I go to ask a question, I notice that the same (or similar) question has already been asked. However, the previous question doesn't have a good answer (or is unanswered). In this case, is it better to ask the question again in a...
The hydroxyl fragment isn't a good leaving group, unless the medium is acidic. Using just HBr, you can convert the hydroxyl group into an oxonium ion (the H2O fragment would be a good leaving group). Upon heterolysis of the C-O bond, a hydride shift occurs simultaneously to create a secondary car...