[scienceguy]

Hi there,

When you are brominating an alkene with N-bromosuccinimide, will the bromine be added to the most highly substituted carbon? I ask this because I know the intermediate is stabilized by resonance.

i.e.  CH3-CH2-CH-CH=CH2 brominated to CH3-CHBr-CH2-CH=CH2 or CH2-CH2-CBr-CH=CH2    ?
                    \                                                  \                                 \
                     CH3                                              CH3                             CH3

[Jorriss]

I'm not sure where you're uncertainty stems from...? The first one isn't the most substitute or resonance stabilized.