Single correct option
A hydrocarbon A () decolourises bromine water. On ozonolysis followed by it gives a single compound B () which gives a positive iodoform test. Warming B with dilute NaOH gives an -unsaturated ketone C by intramolecular aldol condensation. C is
- A. 3-methylcyclohex-2-en-1-one
- B. 1-acetylcyclopentene
- C. 2-methylcyclohex-2-en-1-one
- D. 4-methylcyclohex-2-en-1-one
Show answer and solution
Answer: (A) 3-methylcyclohex-2-en-1-one
A has two degrees of unsaturation, and since ozonolysis gives one product containing both carbonyls, A is a cyclic alkene: 1,2-dimethylcyclopentene. Its reductive ozonolysis opens the ring to heptane-2,6-dione, (B), which has the group needed for the iodoform test. In base, the terminal (C-1) enolate attacks the other carbonyl (C-6), closing a six-membered ring (C1 to C6); dehydration gives 3-methylcyclohex-2-en-1-one, . Attack from C-3 would need a strained four-membered ring.
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