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JEE Main Chemistry question

ChemistryAminesJEE Main

Pyrolysis of the deuterium-labelled amine -oxide (-dimethylethyl--amine -oxide, i.e. trimethylamine -oxide with one methyl replaced by an ethyl- group) would give:

Answer: (D)

Solution

Pyrolysis of a tertiary amine -oxide (Cope elimination) proceeds through a 5-membered cyclic transition state in which the oxide oxygen removes a -hydrogen (or, here, a -deuterium) syn to it, forming a new carbon–carbon double bond on that substituent while the nitrogen leaves as a hydroxylamine. The

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Question ID VK-150329