The compound(s) which will show significant intermolecular H-bonding is/are: (a) o-nitrophenol (b) 4-acetamidophenol…
Chemical Bonding · Class 11 · JEE Main Previous Year Question
The compound(s) which will show significant intermolecular H-bonding is/are:
(a) o-nitrophenol (b) 4-acetamidophenol (paracetamol) (c) 2,4,6-trimethylphenol
- a
(a), (b) and (c)
- b✓
(b) only
- c
(c) only
- d
(a) and (b) only
(b) only
🧠 Intramolecular H-bonding uses up the H-bond donor within the same molecule, reducing availability for intermolecular H-bonds. Steric hindrance near the –OH also prevents intermolecular H-bond formation.
🗺️ Analyse each compound:
(a) o-nitrophenol: –OH and adjacent –NO₂ form a 6-membered intramolecular H-bond ring → the –OH is not available for intermolecular H-bonding → significant intermolecular H-bonding: No ✗
(b) 4-acetamidophenol (paracetamol): Has both phenolic –OH and amide N–H (–NHCOCH₃) at para positions — no intramolecular H-bonding possible due to distance; both groups are accessible → forms extensive intermolecular H-bonds ✓
(c) 2,4,6-trimethylphenol: The two ortho-methyl groups sterically shield the –OH from approaching other molecules → intermolecular H-bonding is hindered ✗
⚡ Only paracetamol has unhindered, non-intramolecularly-blocked H-bond donor groups.
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