Select the compound from the following that will show intramolecular hydrogen bonding:
Chemical Bonding · Class 11 · JEE Main Previous Year Question
Select the compound from the following that will show intramolecular hydrogen bonding:
- a
- b
- c
- d✓
o-nitrophenol
o-nitrophenol
🧠 Intramolecular hydrogen bonding forms within the same molecule — typically when an O–H or N–H group and a lone-pair-bearing atom are on the same molecule, close enough to form a ring.
🗺️ Analyse each option:
- : only intermolecular H-bonding (no intramolecular geometry possible)
- : only intermolecular H-bonding
- : only intermolecular H-bonding (no nearby acceptor group)
- o-nitrophenol: The phenolic –OH and the ortho group are on adjacent carbons. The O–H hydrogen bonds to one oxygen of , forming a 6-membered intramolecular ring → intramolecular H-bonding ✓
⚡ This is why o-nitrophenol has a lower melting and boiling point than p-nitrophenol: the intramolecular H-bond "uses up" the donor, reducing intermolecular associations.
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