JEE Main Chemistry question

The compound CH₃–C(CH₃)=CH–CH₃ (2-methylbut-2-ene) on reaction with NaIO₄ in the presence of KMnO₄ gives

(A)CH₃COCH₃
(B)CH₃COCH₃ + CH₃COOH
(C)CH₃COCH₃ + CH₃CHOCorrect
(D)CH₃CHO + CO₂

Answer: (C)

Solution

2-Methylbut-2-ene, (CH₃)₂C=CH–CH₃, is an unsymmetrically substituted (trisubstituted) alkene: one alkene carbon bears two methyl groups, while the other bears one methyl group and one H. Oxidative cleavage of the C=C bond (NaIO₄/KMnO₄, a Lemieux–von Rudloff-type cleavage that stops at the carbonyl stage) converts the

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Question ID VK-149339