Chemistry - PRACTICAL ORGANIC CHEMISTRY Question with Solution | TestHub

Naphthalene can sublime directly to vapour upon heating, but benzoic acid do not. Related Theory When benzoic acid is heated in presence of $a$ strong dehydrating agent like ${\mathrm{P}}_2{\mathrm{O}}_5$ or ${\mathrm{H}}_2{\mathrm{SO}}_f$ it forms benzoic anhydride. $$2{\mathrm{C}}_6{\mathrm{H}}_5\mathrm{COOH}\underset{{\mathrm{BaOl}}_5}{⟶}{\left({\mathrm{C}}_6{\mathrm{H}}_5\mathrm{CO}\right)}_2\mathrm{O}+{\mathrm{H}}_2\mathrm{O}$$ Caution Naphthalene is volatile and benzoic acid is non-volatile due to the formation of dimer via hydrogen bonding (intermolecular).