O-Acetylation of the N-oxide activates the adjacent methyl group. The Boekelheide rearrangement transfers oxygen functionality to that side chain, removes the N-oxide and restores the aromatic pyridine. The product is 2-(acetoxymethyl)pyridine, C. A and B retain the N-oxide and add an acetyl carbon–carbon bond; D acetoxylates the ring instead.
More Heterocyclic Compounds: Nomenclature of mono- and bicyclic, as well as mono- and di-heteroatomic compounds, Structure, preparation, properties and reactions of furan, pyrrole, thiophene, pyridine, indole, quinoline and isoquinoline. questions
GATE 2024 CY Q25– The reaction(s) that yield(s) 2-methylquinoline as the major product is (are)
GATE 2026 CY Q50– The reaction(s) that produce(s) 2-methylindole as the major product is(are)
GATE 2023 CY Q37– The major product formed in the given reaction sequence is
GATE 2022 CY Q12– The starting material Y in the following reaction is
GATE 2020 CY Q16– The shown ortho-nitrotoluene reacts with diethyl oxalate/NaOEt to give P, followed by…
