An alkyl chloride produces a single alkene on reaction with sodium ethoxide and ethanol. The alkene further undergoes hydrogenation to yield 2-methylbutane. Identify the alkyl chloride amongst the following compounds.

Solution :
\[Cl-C{{H}_{2}}\underset{\begin{smallmatrix} |\,\,\,\,\, \\ C{{H}_{3}}\, \end{smallmatrix}}{\mathop{-CH-}}\,C{{H}_{2}}C{{H}_{3}}\xrightarrow[EtOH]{NaOEt}\]
\[C{{H}_{2}}\underset{\begin{smallmatrix} | \\ \,\,\,C{{H}_{3}} \end{smallmatrix}}{\mathop{=C-}}\,C{{H}_{2}}C{{H}_{3}}\xrightarrow[\text{catalyst}]{{{H}_{2}}}\]       \[\underset{\text{2-Methylbutane}}{\mathop{C{{H}_{3}}\underset{\begin{smallmatrix} |\,\,\,\,\, \\ C{{H}_{3}}\,\, \end{smallmatrix}}{\mathop{-CH-}}\,C{{H}_{2}}C{{H}_{3}}}}\,\]