JEE Main Chemistry question

Which set of products is expected on reductive ozonolysis of the diolefin 3-methylpenta-1,3-diene, CH₂=CH–C(CH₃)=CH–CH₃?

(A)CH₃CHO; CH₃COCH=CH₂; CH₂O
(B)CH₃CH=C(CH₃)OH; CH₂O
(C)CH₃CHO; CH₃COCHO; CH₂OCorrect
(D)CH₃CHO; CH₃COCH₃; CH₂O

Answer: (C)

Solution

The diene has two C=C bonds: C1=C2 (terminal CH₂=CH–) and C3=C4 (the C(CH₃)=CH– unit), joined by the C2–C3 single bond, which survives ozonolysis. Cleaving C1=C2 converts the terminal =CH₂ into HCHO and C2 into a –CHO carbon. Cleaving C3=C4

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Question ID VK-149048