Complete ozonolysis (followed by reductive cleavage) of a perfect, unbranched cis-1,4-polyisoprene c — Polymers Chemistry Question
Question
Complete ozonolysis (followed by reductive cleavage) of a perfect, unbranched cis-1,4-polyisoprene chain yields predominantly a specific dicarbonyl compound. How many oxygen atoms are present in a single molecule of this primary product?
Answer: 2
💡 Solution & Explanation
The repeating unit is $[-CH_2-C(CH_3)=CH-CH_2-]$. Ozonolysis cleaves the $C=C$ double bond, yielding 4-oxopentanal (levulinaldehyde), which has the structure $CH_3-CO-CH_2-CH_2-CHO$. This molecule contains 1 ketone oxygen and 1 aldehyde oxygen, totaling 2 oxygen atoms.
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