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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc234

The cyclic diene shown is subjected to ozonolysis with reductive work-up. Which statements are correct?

  1. ATwo distinct carbonyl compounds are formed.
  2. BOne product contains both an aldehyde group and a ketone group.
  3. CWith work-up, propanedioic acid is one of the products.
  4. DBoth products are dialdehydes.

Answer: A, B, C

The compound shown is 1-methylcyclohexa-1,4-diene. Cleaving both double bonds gives 3-oxobutanal (, from the methyl-bearing end) and propanedial (, from the central unit). Oxidative work-up would oxidise the dialdehyde to propanedioic (malonic) acid. Only the central unit is a dialdehyde, so the last statement is wrong.
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