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JEE Advanced levelNumerical answerDifficulty 3 of 3g2243

The compound shown has several nitrogen atoms. Count the nitrogen atoms whose lone pair can accept a proton from dilute acid. Treat as non-basic any nitrogen whose lone pair is delocalised into a pi system (amide N, N attached directly to the electron-poor pyridine ring); the in-plane lone pair of a pyridine-type ring nitrogen counts as available. Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 2

The amide NH2 lone pair is delocalised onto C=O. The piperazine nitrogen bonded to the pyridine ring is conjugated with the ring and treated as non-basic. The pyridine ring nitrogen (in-plane sp2 lone pair) and the secondary amine N-H of piperazine (sp3, localised) are basic. Number of basic nitrogens = 2.
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