Question
Out of o-nitrophenol and p-nitrophenol, which is more volatile? Explain.

Answer

Ortho nitrophenol is much more volatile in steam due to chelation. Intramolecular hydrogen bonding is present in o-nitrophenol and intermolecular hydrogen bonding in p-nitrophenol.

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$\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Br}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{CH}_3-\text{CH}-\text{CH}-\text{CH}_3\xrightarrow{\ \ \ \text{HBr} \ \ }\text{CH}_3-\text{C}-\text{CH}_2-\text{CH}_3\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3\ \ \ \ \text{OH}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{CH}_3$

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