JEE Main · 2021 · Shift-IImediumBOND-147

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

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

Options
  1. a

    (a), (b) and (c)

  2. b

    (b) only

  3. c

    (c) only

  4. d

    (a) and (b) only

Correct Answerb

(b) only

Detailed Solution

🧠 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.

Answer: (b) only — 4-acetamidophenol (paracetamol)\boxed{\text{Answer: (b) only — 4-acetamidophenol (paracetamol)}}

Practice this question with progress tracking

Want timed practice with adaptive difficulty? Solve this question (and hundreds more from Chemical Bonding) inside The Crucible, our adaptive practice platform.

The compound(s) which will show significant intermolecular H-bonding is/are: (a) o-nitrophenol (b)… (JEE Main 2021) | Canvas Classes