Identify the binary mixture(s) that can be separated into individual compounds, by differential extraction…
Identify the binary mixture(s) that can be separated into individual compounds, by differential extraction as shown in the given scheme.
$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}$
$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}$
$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}$
$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}$ and $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{COOH}$
Solution
(a) Both are soluble in $\mathrm{NaOH}$. Hence, inseparable.
(b) Only benzoic acid $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\right)$ is soluble in $\mathrm{NaOH}$ and $\mathrm{NaHCO}_{3}$, while benzyl alcohol $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\right)$ is not. Hence, separable.
(c) Although $\mathrm{NaOH}$ can enable separation between benzyl alcohol $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\right)$ and phenol $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\right)$ as only the latter is soluble in $\mathrm{NaOH}$. However, in $\mathrm{NaHCO}_{3}$, both are insoluble. Hence, inseparable.
(d) $\alpha$-Phenylacetic acid $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{COOH}\right)$ is soluble in $\mathrm{NaOH}$ and $\mathrm{NaHCO}_{3}$, while benzyl alcohol $\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\right)$ is not. Hence, separable.
