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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc198

A hydrocarbon undergoes a Diels-Alder reaction with maleic anhydride. Its reductive ozonolysis gives only methanal and butane-2,3-dione. The hydrocarbon is:

  1. AHexa-1,3-diene
  2. BHexa-1,5-diene
  3. C2,3-Dimethylbuta-1,3-diene
  4. DCyclohexa-1,3-diene

Answer: C

is conjugated and on cleavage gives 2 and . Hexa-1,3-diene would give propanal and glyoxal as well as methanal. Hexa-1,5-diene is not conjugated and gives butanedial. Cyclohexa-1,3-diene gives glyoxal and butanedial.
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