Single correct option
Which of the following alkenes, on reductive ozonolysis ( then ), gives a single product that answers both Tollens' test and the iodoform test?
- A. 1-Methylcyclopentene
- B. Cyclohexene
- C. 1,2-Dimethylcyclohexene
- D. Methylenecyclohexane
Show answer and solution
Answer: (A) 1-Methylcyclopentene
1-Methylcyclopentene is cleaved at the ring double bond to give one open-chain compound (5-oxohexanal). It has a CHO group (Tollens' positive) and a 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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