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JEE Main levelSingle correct optionDifficulty 2 of 3hc275

An alkene A gives the compound shown as its only organic product on ozonolysis followed by . Which structure is A?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

The compound shown is pentanedioic (glutaric) acid. A five-carbon chain with carboxyl groups at both ends comes from cleaving the double bond of cyclopentene, since all five ring carbons are retained. Cyclohexene would give hexanedioic acid, and the two cyclic dienes would each give two different acids (cyclopentadiene gives oxalic and malonic acids).
Practice Hydrocarbons More on Alkene identification from ozonolysis data and side-chain oxidation of alkylbenzenes

More questions on Alkene identification from ozonolysis data and side-chain oxidation of alkylbenzenes