$C{{H}_{3}}-CH=C{{H}_{2}}\xrightarrow{HBr}\underset{2-bromopropane}{\mathop{\begin{matrix}
   C{{H}_{3}}-CH-C{{H}_{3}}  \\
   |\,\,\,\,  \\
   Br\,  \\
\end{matrix}}}\,$

$C{{H}_{3}}-C\equiv CH\xrightarrow{HBr}\begin{matrix}
   C{{H}_{3}}-C=C{{H}_{2}}  \\
   |  \\
   Br  \\
\end{matrix}$ $\xrightarrow{{HBr}}\mathop {\begin{array}{*{20}{c}}
  {\,Br} \\ 
  | \\ 
  {C{H_3} - C - C{H_3}} \\ 
  | \\ 
  {\,Br} 
\end{array}}\limits_{2,2 - dibromopropane} $

$C{H_3}CH = CHBr\xrightarrow{{HBr}}\mathop {\begin{array}{*{20}{c}}
  {C{H_3} - CH - C{H_2}Br} \\ 
  {|\,\,\,\,\,\,\,\,\,\,} \\ 
  {\,Br\,\,\,\,\,\,\,\,\,} 
\end{array}}\limits_{1,2 - dibromopropane} $