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Natural rubber on complete ozonolysis ( O ₃ /Zn- H ₂ O ) gives compound X as the major product. X gives positive iodoform and Tollen's tests. X on heating with aqueous NaOH gives Y as the major product. Y is

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Natural rubber is cis-1,4-polyisoprene, with the repeating unit [- CH ₂- C ( CH ₃)= CH - CH ₂-]_n . Complete reductive ozonolysis ( O ₃ /Zn- H ₂ O ) of natural rubber cleaves the double bonds to give 4-oxopentanal (levulinaldehyde) as compound X. [- CH ₂- C ( CH ₃)= CH - CH ₂-]_n O ₃/ Zn-H ₂ O n CH ₃- C (= O )- CH ₂- CH ₂- CHO Compound X ( CH ₃- CO - CH ₂- CH ₂- CHO ) has a methyl ketone group, which gives a positive iodoform test, and an aldehyde group, which gives a positive Tollen's test. When X is heated with a

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