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What is the major organic product formed when 1-methylcycloheptene is subjected to ozonolysis followed by heating with dilute NaOH?

Options

  1. A2-Methylcyclohex-1-ene-1-carbaldehyde
  2. B1-Acetylcycloheptene
  3. C1-Acetylcyclohexene
  4. D3-Acetylcyclohexene

Correct answer

C. 1-Acetylcyclohexene

Step-by-step solution

Ozonolysis of 1-methylcycloheptene cleaves the double bond to form the 8-carbon keto-aldehyde, 2-oxooctanal ( CH₃-CO-CH₂-CH₂-CH₂-CH₂-CH₂-CHO ). Under basic conditions, an intramolecular aldol condensation occurs. The enolate can form at the -carbon of the ketone or the aldehyde. Since aldehydes are more electrophilic than ketones, the enolate of the ketone preferentially attacks the aldehyde group. Deprotonation at the CH₂ adjacent to the ketone forms an enolate that attacks the aldehyde carbon, forming a stable 6-

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