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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc144

Limonene is 1-methyl-4-(prop-1-en-2-yl)cyclohexene, , with one ring double bond and one isopropenyl double bond. It is treated with excess , followed by dimethyl sulfide. Which description is correct?

  1. A2 mol of are consumed per mole, and two organic products form: methanal and one acyclic keto-aldehyde-ketone
  2. B2 mol of are consumed per mole, and three organic products form: methanal, propanone and a cyclic ketone
  3. C1 mol of is consumed per mole, and two organic products form
  4. D3 mol of are consumed per mole, and the product is a single compound

Answer: A

Limonene has two C=C bonds, so 2 mol of ozone are used. The ring bond opens to give a chain with at one end and CHO at the other. The isopropenyl group becomes on the ring carbon and releases . The ring is opened, so the second product is one acyclic compound () plus methanal.
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