Question

Which of the following alcohols will yield the corresponding alkyl chloride on reaction with concentrated HCl at room temperature?

Options

• \[\ce{CH3CH2-CH2-OH}\]

• \[\begin{array}{cc}
  \phantom{.}\ce{CH3CH2-CH-OH}\\
  \phantom{.......}|\\
  \phantom{............}\ce{CH3}\\
  \end{array}\]

• \[\begin{array}{cc}
  \phantom{.}\ce{CH3CH2-CH-CH2-OH}\\
  \phantom{}|\\
  \phantom{.....}\ce{CH3}\\
  \end{array}\]

• \[\begin{array}{cc}
  \phantom{............}\ce{CH3}\\
  \phantom{........}|\\
  \phantom{}\ce{CH3CH2-C-OH} \\
  \phantom{........}|\\\phantom{.............}\ce{CH3}\\
  \end{array}\]\[\begin{array}{cc}
  \end{array}\]

Answer 1

\[\begin{array}{cc}
\phantom{............}\ce{CH3}\\
\phantom{........}|\\
\phantom{}\ce{CH3CH2-C-OH} \\
\phantom{........}|\\\phantom{.............}\ce{CH3}\\
\end{array}\]\[\begin{array}{cc}
\end{array}\]

Explanation: 

As tertiary carbocation is more stable, so tertiary alcohols will yield the corresponding alkyl chloride on reaction with concentrated HCl at room temperature.