JEE Main Chemistry question

The product of Cope elimination (pyrolysis) of (cyclohexylmethyl)dimethylamine -oxide, , is

(A)cyclohexyl- (unreacted starting material)
(B)cyclohexyl- (a protonated amine salt)
(C)cyclohexylidene (ring) Correct
(D)ring (a quaternary salt adduct)

Answer: (C)

Solution

In Cope elimination, the -oxide oxygen itself acts as an intramolecular base, removing a -hydrogen from the ring carbon adjacent to the exocyclic group through a 5-membered cyclic transition state. This forms a new ring-to-exocyclic C=C double bond (giving

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Question ID VK-150339