Given : [figure] The enthalpy of hydrogenation of these compounds will be in the order as
- II > III > I
- II > I > III
- I > II > III
- III > II > I
Answer
(4) III > II > I
Solution
All three compounds take up 3 mol H2 and give the same product, 1,3,5-trimethylcyclohexane.
⇒ The less stable the starting compound, the more heat is released on hydrogenation.
I (mesitylene) is aromatic ⇒ large resonance stabilisation ⇒ most stable ⇒ least enthalpy of hydrogenation.
II has three conjugated C=C (non-aromatic) ⇒ some stabilisation by conjugation.
III has three isolated exocyclic C=C ⇒ no conjugation ⇒ least stable ⇒ largest enthalpy of hydrogenation.
∴ III > II > I
Answer: (4)