JEE Main · 2020 · Shift-IhardBOND-168

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

Question

Among the compounds A and B with molecular formula C9H18O3\mathrm{C_9H_{18}O_3}, 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

Options
  1. a

    Option 1

  2. b

    Option 2

  3. c

    Option 3

  4. d

    Option 4

Correct Answerc

Option 3

Detailed Solution

🧠 Two isomers with formula C9H18O3\mathrm{C_9H_{18}O_3}: 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).

Answer: A = 1,3,5-tris(hydroxymethyl)cyclohexane; B = 1,3,5-trimethoxycyclohexane\boxed{\text{Answer: A = 1,3,5-tris(hydroxymethyl)cyclohexane; B = 1,3,5-trimethoxycyclohexane}}

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