Among the compounds A and B with molecular formula C9H18O3, A has a higher boiling point than B. The possible…
Chemical Bonding · Class 11 · JEE Main Previous Year Question
Among the compounds A and B with molecular formula , A has a higher boiling point than B. The possible structures of A and B are:
(1) A = 1,3,5-trimethoxycyclohexane; B = 1,3,5-trimethoxycyclohexane (2) A = 1,3,5-trimethoxycyclohexane; B = 1,3,5-trimethoxycyclohexane (3) A = 1,3,5-tris(hydroxymethyl)cyclohexane; B = 1,3,5-trimethoxycyclohexane (4) A = 1,3,5-trimethoxycyclohexane; B = 1,3,5-tris(hydroxymethyl)cyclohexane
- a
Option 1
- b
Option 2
- c✓
Option 3
- d
Option 4
Option 3
🧠 Two isomers with formula : one has –OCH₃ ether groups (no O–H), the other has –CH₂OH groups (with O–H). The one with O–H has much higher boiling point due to H-bonding.
🗺️ Identify the structures:
1,3,5-trimethoxycyclohexane: Three –OCH₃ ether groups
- No O–H bonds → no H-bond donor capability
- Only van der Waals and weak dipole–dipole forces
- Lower boiling point → this is B
1,3,5-tris(hydroxymethyl)cyclohexane: Three –CH₂OH groups
- Three O–H bonds → extensive intermolecular H-bonding (three donors per molecule)
- Much stronger intermolecular association
- Higher boiling point → this is A
⚡ The molecule with O–H groups always has a significantly higher boiling point than its ether isomer — H-bonds (20–40 kJ/mol per bond) are far stronger than dipole–dipole forces (2–5 kJ/mol).
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