JEE MainChemistryHydrocarbons
A hydrocarbon 'Y' with the molecular formula C ₈ H ₁₂ absorbs two moles of H ₂ on catalytic hydrogenation. On reductive ozonolysis, one mole of 'Y' yields one mole of hexane- 2,5 -dione and one mole of ethanedial. The hydrocarbon 'Y' is :
Options
- A1,4 -dimethylcyclohexa- 1,4 -diene
- B1,4 -dimethylcyclohexa- 1,3 -diene
- C2,3 -dimethylcyclohexa- 1,3 -diene
- D1,2 -dimethylcyclohexa- 1,4 -diene
Correct answer
B. 1,4 -dimethylcyclohexa- 1,3 -diene
Step-by-step solution
Degree of unsaturation (DBE) for C ₈ H ₁₂ = 8 + 1 - 12 2 = 3 . Since one mole of 'Y' absorbs two moles of H ₂ , it contains two double bonds. The remaining 1 DBE indicates the presence of one ring. Reductive ozonolysis of 'Y' yields hexane- 2,5 -dione ( CH ₃ COCH ₂ CH ₂ COCH ₃ ) and ethanedial ( OHC - CHO ). To find the structure of 'Y', we perform a retrosynthetic analysis by removing the oxygen atoms from the carbonyl groups of the products and connecting the respective carbon atoms with double bonds. Aligning th