JEE Advanced levelSingle correct optionDifficulty 3 of 3pl181
Ozonolysis of natural rubber followed by reductive work-up (Zn/HX2O) cleaves every C=C of the 1,4-polyisoprene chain. The main product is
ACHX3−CO−CHX2−CHX2−CHO (4-oxopentanal)
BCHX3−CO−CHX2−CO−CHX3 (pentane-2,4-dione)
COHC−CH(CHX3)−CHX2−CHO (2-methylbutanedial)
DCHX3−CO−CHX3 (propanone) and HCHO
Answer: A
The repeat unit is −CHX2−C(CHX3)=CH−CHX2X−. Cleaving the C=C converts C(CHX3)= into a ketone and =CHX− into an aldehyde. Each repeat unit therefore becomes CHX3−CO−CHX2−CHX2−CHO.