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all right so it turns out instead of using hbr for both primary and secondary alcohols thereamp;#39;s an alternative and thatamp;#39;s using pbr3 here in this case itamp;#39;s only works for primary technicals because it goes through an sn2 mechanism and you canamp;#39;t do sn2 on a tertiary carbon so thatamp;#39;s why you canamp;#39;t use this with tertiary alcohols but for primary and secondary alcohols itamp;#39;s a great alternative and in this case it always goes sn2 thereamp;#39;s no of this debate as a test and one or is it sn2 itamp;#39;s always sn2 and in this case being sn2 if it happens at a chiral center you do have to worry about inversion of configuration as Iamp;#39;ve got diagrammed right here letamp;#39;s kind of take a look at how the mechanism works here so first step as your alcohols gonna come and attack phosphorus causing one of the bro means to leave so your phosphorus is still domina - bro means and then you still have another bromide ion now floating
