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What technique would you use to separate...

What technique would you use to separate the following mixtures ?
A mixture of benzoic acid and naphthalene.

Text Solution

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Both these solids sublime on heating. Therefore, these cannot be separated by sublimation. The mixture is heated with water when only benzoic acid will dissolve. Upon filtration, naphthalene is separated and the solution upon cooling gives crystals of benzoic acid.
Alternatively the mixture is reacted with strong aqueous sodium hydroxide when benzoic acid is converted to soluble sodium benzoate whie napthalene is unaffected. It can be separated by filtration. the filtrate is then treated with dilute `HCl` to regenerate benzoic acid.
`underset("Benzoic acid")(C_(6)H_(5)COOH)(s)+NaOH(aq) rarr underset("Sod. benzoate")(C_(6)H_(5)COONa(aq))+H_(2)O`
`C_(6)H_(5)COONa(aq) + HCl (aq) rarr underset("(White ppt.)")(C_(6)H_(5)COOH (s))+NaCl (aq)`
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