JEE MAIN - Chemistry (2012 - No. 20)

Ortho–Nitrophenol is less soluble in water than p– and m– Nitrophenols because :
o–Nitrophenol is more volatile in steam than those of m – and p–isomers
o–Nitrophenol shows Intramolecular H–bonding
o–Nitrophenol shows Intermolecular H–bonding
Melting point of o–Nitrophenol is lower than those of m–and p–isomers.

Explanation

As in ortho-Nitrophenol H of -OH is already in Intra-moleculer H Bond and become stable so it will not perticipate in H bonding with H2O by breaking this H bonding. That is why solublity of Ortho–Nitrophenol is less in water. AIEEE 2012 Chemistry - Alcohols, Phenols and Ethers Question 167 English Explanation 1

para– and meta– Nitrophenols both shows inter-moleculer H bonding with H2O. That is why both are more soluble in water.

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