\(\underset{\begin{smallmatrix}
2\,-\,oc\tan ol \\
(optically\,\,active)
\end{smallmatrix}}{\mathop{\begin{matrix}
C{{H}_{3}}-\overset{*}{\mathop{C}}\,H-{{(C{{H}_{2}})}_{5}}-C{{H}_{3}} \\
|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
:\underset{\scriptscriptstyle\centerdot\centerdot}{O}H\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
\end{matrix}}}\,\)\(\xrightarrow{{dil\,.\,acid}}\,C{H_3} - CH = CH - {(C{H_2})_4} - C{H_3}\)
$I. \,\,C{H_2} = CHC{H_2}Cl$
$II.\,\,C{H_3}C{H_2}C{H_2}Br$
$III.\,\,{(C{H_3})_3}CC{H_2}Br$
$IV.\,\,C{H_3}C{H_2}C{H_2}Cl$