An alkene  ${\mathrm{C}}_6{\mathrm{H}}_{12}$ (A) undergoes oxidative ozonolysis to give two different acids (B) and (C).Neither (B) nor (C) contains more than four carbon atoms. How many alkenes can satisfy these criteria? (Consider only structural isomers)

When a C₆H₁₂ alkene undergoes oxidative ozonolysis, it cleaves the carbon-carbon double bond, resulting in two carboxylic acids. Given that neither of these acids contains more than four carbon atoms, we need to identify the alkenes that can produce such products.

Analysis:

• Possible Carboxylic Acids: The carboxylic acids with up to four carbon atoms are:
  • Acetic Acid (C₂H₄O₂): Two carbon atoms.
  • Propanoic Acid (C₃H₆O₂): Three carbon atoms.
  • Butanoic Acid (C₄H₈O₂): Four carbon atoms.
• Alkene Structure: For the ozonolysis of a C₆H₁₂ alkene to yield two different acids, the alkene must have a structure that, upon cleavage, produces these acids.

Possible Alkenes:

1. 1,5-Hexadiene: The double bond between C₁ and C₂ yields acetic acid, and the double bond between C₄ and C₅ yields butanoic acid.
2. 1,4-Hexadiene: The double bond between C₁ and C₂ yields acetic acid, and the double bond between C₃ and C₄ yields propanoic acid.
3. 1,3-Hexadiene: The double bond between C₁ and C₂ yields acetic acid, and the double bond between C₂ and C₃ yields propanoic acid.
4. 2,4-Hexadiene: The double bond between C₂ and C₃ yields propanoic acid, and the double bond between C₄ and C₅ yields propanoic acid.

Final Answer

There are four structural isomers of C₆H₁₂ alkenes that, upon oxidative ozonolysis, yield two different carboxylic acids, each containing no more than four carbon atoms.