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CGP EDU Academic Team
Published on: August 13, 2026
When semicarbazide reacts with a ketone (or aldehyde) to form semicarbazone. Only one nitrogen atom of semicarbazide acts as a nucleophile and attack the carbonyl carbon of the ketone. The product of the reaction consequently is R 2 C=N–NH–CONH 2 rather than R 2 C=NCONH–NH 2 . What factor account for the fact that two nitrogen atoms of semicarbazide are relatively non nucleophilic ?
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Two nitrogen atoms of semicarbazide that are adjacent to the (C=O) group have their lone pair present in conjugation so nucleophilicity decreases.
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