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JEE Main 2022 · Chemistry · Hydrocarbons · hard

A hydrocarbon A (C7H12) decolourises bromine water. On ozonolysis followed by Zn/H2O it gives a single compound B (C7H12O2) which gives a positive…

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A hydrocarbon A (C7H12\mathrm{C_7H_{12}}) decolourises bromine water. On ozonolysis followed by Zn/H2O\mathrm{Zn/H_2O} it gives a single compound B (C7H12O2\mathrm{C_7H_{12}O_2}) which gives a positive iodoform test. Warming B with dilute NaOH gives an α,β\alpha,\beta-unsaturated ketone C by intramolecular aldol condensation. C is
  1. A. 3-methylcyclohex-2-en-1-one
  2. B. 1-acetylcyclopentene
  3. C. 2-methylcyclohex-2-en-1-one
  4. D. 4-methylcyclohex-2-en-1-one
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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, CH3COCH2CH2CH2COCH3\mathrm{CH_3COCH_2CH_2CH_2COCH_3} (B), which has the CH3CO−\mathrm{CH_3CO-} group needed for the iodoform test. In base, the terminal CH3\mathrm{CH_3} (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, C7H10O\mathrm{C_7H_{10}O}. Attack from C-3 would need a strained four-membered ring.
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