JEE Main · 2024 · Shift-IIeasyBOND-142

Select the compound from the following that will show intramolecular hydrogen bonding:

Chemical Bonding · Class 11 · JEE Main Previous Year Question

Question

Select the compound from the following that will show intramolecular hydrogen bonding:

Options
  1. a

    H2O\mathrm{H_2O}

  2. b

    NH3\mathrm{NH_3}

  3. c

    C2H5OH\mathrm{C_2H_5OH}

  4. d

    o-nitrophenol

Correct Answerd

o-nitrophenol

Detailed Solution

🧠 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:

  • H2O\mathrm{H_2O}: only intermolecular H-bonding (no intramolecular geometry possible)
  • NH3\mathrm{NH_3}: only intermolecular H-bonding
  • C2H5OH\mathrm{C_2H_5OH}: only intermolecular H-bonding (no nearby acceptor group)
  • o-nitrophenol: The phenolic –OH and the ortho NO2\mathrm{–NO_2} group are on adjacent carbons. The O–H hydrogen bonds to one oxygen of NO2\mathrm{–NO_2}, 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.

Answer: o-nitrophenol\boxed{\text{Answer: o-nitrophenol}}

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