How to convert CH3-CHBr-CH3 into CH3-CHOH-CH2Br ?
i would prefer if anyone could give me the answer in minimum number of steps =)
i would prefer if anyone could give me the answer in minimum number of steps =)
1 Answer
Huh, I can't think of more than one good path. There are others, but they won't give as good of a yield because the alkyl halide is a secondary alkyl halide, which is not great for
Here's what I came up with:
The first step is a second order elimination (
The second step is not one you would normally think you need to use (it might have been introduced as a reaction you want to try to avoid happening when brominating), but it works here.
Bromine adds across the double bond first as a cyclopropane analog, and then water, as a stronger nucleophile, intercepts before the other bromine attacks.
Water targets the carbon where the resultant carbocation is more stable, so it targets carbon-2. The result is a product of Markovnikov anti addition (as opposed to syn addition).