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$1. \,{H_3}C - \mathop O\limits^ + {H_2} \to CH_3^ + + {H_2}O$
$2.\,{(C{H_3})_3}C - \mathop O\limits^ + {H_2} \to {(C{H_3})_3}{C^ + } + {H_2}O$
$3.\,{(C{H_3})_2}CH - \mathop O\limits^ + {H_2} \to {(C{H_3})_2}C{H^ + } + {H_2}O$
$\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\
{C{H_3} - CH - C{H_2} - C - C{H_3}} \\
{\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\
{\,\,\,\,\,\,\,OH\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH\,}
\end{array}$ and $\begin{array}{*{20}{c}}
{C{H_2} - CH - C{H_2}} \\
{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,} \\
{CN\,\,\,\,\,\,\,\,CN\,\,\,\,\,\,\,\,CN\,\,}
\end{array}$