In which case first has higher solubility than second?
(I) Phenol, Benzene
(II) Nitrobenzene, Phenol
(III) o-Hydroxybenzaldehyde, p-Hydroxy benzaldehyde
(IV) $C H_{3} C H O, C H_{3} - O - C H_{3}$
(V) o-Nitrophenol, p-Nitrophenol

Only I

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III, V

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I, IV

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II, IV

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Solution

The correct option is C I, IV
(I) Phenol has a higher solubility than benzene due to a presence of polar $- O H$ group which can form hydrogen bonds with water.
(II) Nitrobenzene has lower solubility than phenol as phenol contains polar $- O H$ group which can form hydrogen bonds with water.
(III) o-hydroxybenzaldehyde has lower solubility than p-hydroxybenzaldehyde as o--hydroxybenzaldehyde forms intramolecular hydrogen bonds whereas p-hydroxybenzaldehyde forms intermolecular hydrogen bonds with water.
(IV) Acetaldehyde has a higher solubility than dimethyl ether due to a presence of polar carbonyl group which can form hydrogen bonds with water.

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