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JEE Main 2016 · Chemistry · Hydrocarbons · medium

Alkenes, on reductive ozonolysis (O3 then Zn/H2O), gives a single product that answers both Tollens' test and the iodoform test?

Single correct option

Which of the following alkenes, on reductive ozonolysis (O3\mathrm{O_3} then Zn/H2O\mathrm{Zn/H_2O}), gives a single product that answers both Tollens' test and the iodoform test?
  1. A. 1-Methylcyclopentene
  2. B. Cyclohexene
  3. C. 1,2-Dimethylcyclohexene
  4. D. Methylenecyclohexane
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Answer: (A) 1-Methylcyclopentene

1-Methylcyclopentene is cleaved at the ring double bond to give one open-chain compound CH3CO(CH2)3CHO\mathrm{CH_3CO(CH_2)_3CHO} (5-oxohexanal). It has a CHO group (Tollens' positive) and a CH3CO−\mathrm{CH_3CO-} group (iodoform positive). Cyclohexene gives hexanedial: Tollens' positive, iodoform negative. 1,2-Dimethylcyclohexene gives octane-2,7-dione: iodoform positive but no CHO. Methylenecyclohexane gives two products, cyclohexanone and methanal, so it fails the 'single product' condition and neither responds to both tests.
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