- A$C{H_3} - CHOH - C{H_2} - C{H_3}$
- ✓${(C{H_3})_3} - C - OH$
- C$C{H_3} - C{H_2} - C{H_2} - C{H_2} - OH$
- D${(C{H_3})_3} - CH - C{H_2}OH$
$\begin{array}{*{20}{c}}
{\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,C{H_3}} \\
{\,\,\, \downarrow }
\end{array}} \\
{C{H_3} \to C - OH} \\
{\,\,\,\,\, \uparrow } \\
{\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$ $ \to $ $\begin{array}{*{20}{c}}
{\begin{array}{*{20}{c}}
{\,\,\,\,\,C{H_3}} \\
|
\end{array}\,\,\,} \\
{C{H_3} - {C^ + } + O{H^ - }} \\
{|\,\,\,\,} \\
{\,\,C{H_3}}
\end{array}$
Presence of $3$ alkyl group increases electron density on ${3^o}$ carbon atom.
Hence $ - OH$ group is easily removed.
After the removal of $ - OH$ group ${3^o}$ carbonium ion is formed which is most stable
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$3\underset{\raise0.3em\hbox{$\smash{\scriptscriptstyle-}$}}{B} \xrightarrow{{4\,HCl}}\mathop {2C}\limits_{(Purple)} + Mn{O_2} + 2{H_2}O$
$3\underset{\raise0.3em\hbox{$\smash{\scriptscriptstyle-}$}}{C} \xrightarrow{{{H_2}O,KI}}2\underset{\raise0.3em\hbox{$\smash{\scriptscriptstyle-}$}}{A} + 2KOH + \underset{\raise0.3em\hbox{$\smash{\scriptscriptstyle-}$}}{D} $
In the above sequence of reactions, $\underset{\raise0.3em\hbox{$\smash{\scriptscriptstyle-}$}}{A}$ and $\underset{\raise0.3em\hbox{$\smash{\scriptscriptstyle-}$}}{D} $ , respectively are