MolSynapsequestion bank
MolSynapse / Question bank / Hydrocarbons / Ozonolysis and oxidative cleavage
JEE Advanced levelSingle correct optionDifficulty 3 of 3hc141

1-Methylcyclohexene is treated with followed by . The organic product is

  1. A6-oxoheptanoic acid
  2. B6-oxoheptanal
  3. Cheptanedioic acid
  4. D1-methylcyclohexane-1,2-diol

Answer: A

The ring double bond () is cleaved. C1 (fully substituted) becomes a ketone ; C2 bears H and becomes CHO, which the oxidative work-up converts into COOH. The chain is , 6-oxoheptanoic acid. The aldehyde (6-oxoheptanal) would be obtained with Zn/H2O.
Practice Hydrocarbons More on Ozonolysis and oxidative cleavage

More questions on Ozonolysis and oxidative cleavage