$w.r.t.$ the question asked, $1$ -pentanol has maximum number of carbons, so it is least soluble in water. $\{$ extent of $H-$ bonding decreases $\}$
મિથેનોલ, ફિનોલ, $p-$ ઇથોક્સિફિનોલ
$\begin{array}{*{20}{c}}
{OH\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{C{H_3}CHC{H_2}C{H_2}N{H_2}}
\end{array}$ $\xrightarrow[{triethyla\min e}]{{ethyl\,formate\,\left( {1\,equiv} \right)}}$
${C_6}{H_5}C{H_2}CH(OH)CH{(C{H_3})_2}\xrightarrow{{conc.\,{H_2}S{O_4}}}\,?$