JEE MainChemistryHydrocarbons
An unknown hydrocarbon X ( C₆H₁₀ ) undergoes reductive ozonolysis to yield a single product Y . When Y is treated with excess iodine and aqueous NaOH , it produces a yellow precipitate of iodoform along with the disodium salt of succinic acid. The IUPAC name of hydrocarbon X is
Options
- A1-methylcyclopentene
- Bcyclohexene
- C3-methylcyclopentene
- D1,2-dimethylcyclobutene
Correct answer
D. 1,2-dimethylcyclobutene
Step-by-step solution
The formation of iodoform ( CHI₃ ) upon treatment with I₂/NaOH indicates that the product Y contains at least one methyl ketone group ( -COCH₃ ). The formation of the disodium salt of succinic acid ( NaOOC-CH₂-CH₂-COONa ) along with iodoform from a single molecule Y implies that Y is a diketone that undergoes a double haloform reaction. Working backwards, the structure of Y must be hexane-2,5-dione ( CH₃-CO-CH₂-CH₂-CO-CH₃ ). Since Y is the sole product of the reductive ozonolysis of X ( C₆H₁₀ ), X must be a cyclic