Alcohol To Alkyl Bromide

#Chemistry

Reagents

$\displaystyle \ce{PBr_{3}}$

Mechanism: SN2

  1. $\displaystyle \ce{O}$ from $\displaystyle \ce{OH}$ attacks $\displaystyle \ce{P}$, which kicks off a $\displaystyle \ce{Br-}$
  2. $\displaystyle \ce{Br-}$ back side attacks the $\displaystyle \alpha$ carbon, kicking off $\displaystyle \ce{{}^{-}O-PBr_{2}}$ and creating $\displaystyle \ce{R-Br}$
  3. Steps 1-2 occur 2 more times, resulting in $\displaystyle \ce{H_{3}PO_{4}}$ being produced and 3 total $\displaystyle \ce{R-Br}$