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In the first step, due to the selectivity of bromine in a free radical reaction, the tertiary carbon which has a $\ce{-CH3}$ group attached to it forms the radical. Now, since the radical is a $\ce{^{.}CR3}$ radical, the carbon radical in the intermediate becomes $\ce{sp^2}$. This means that $\ce{^{.}Br}$ can attack from both the top and the bottom since ...

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