Question

An alkyl chloride on Wurtz reaction gives 2,2,5,5-tetramethylhexane. The same alkyl chloride on reduction with a zinc-copper couple in alcohol gives hydrocarbon with molecular formula \[\ce{C5H12}\]. What is the structure of alkyl chloride?

Options

• \[\begin{array}{cc}
  \ce{CH3}\\
  |\phantom{...}\\
  \ce{CH3-C-CH2Cl}\\
  |\phantom{...}\\
  \ce{CH3}
  \end{array}\]

• \[\begin{array}{cc}
  \ce{CH3\phantom{..}}\\
  |\phantom{.....}\\
  \ce{CH3-C-CH2CH3}\\
  |\phantom{.....}\\
  \ce{Cl\phantom{....}}
  \end{array}\]

• \[\begin{array}{cc}
  \ce{CH3-CH2-CH-Cl}\\
  \phantom{......}|\\
  \ce{\phantom{.........}CH3}
  \end{array}\]

• \[\begin{array}{cc}
  \ce{CH3-CH-CH-CHCl}\\
  |\phantom{.....}|\phantom{...}\\
  \ce{\phantom{..}CH3} \ce{\phantom{..}CH3\phantom{..}}
  \end{array}\]

Answer 1

\[\begin{array}{cc}
\ce{CH3}\\
|\phantom{...}\\
\ce{CH3-C-CH2Cl}\\
|\phantom{...}\\
\ce{CH3}
\end{array}\]